Refactored all synchronizers to deal with some of the chronic issues.

Wino.Core.Domain/Entities/Shared/MailAccount.cs

@@ -106,6 +106,12 @@ public class MailAccount
     [Ignore]
     public MailAccountPreferences Preferences { get; set; }
 
+    /// <summary>
+    /// Last time folder structure was synchronized.
+    /// Used for optimization - skip folder sync if synced recently.
+    /// </summary>
+    public DateTime? LastFolderStructureSyncDate { get; set; }
+
     /// <summary>
     /// Gets whether the account can perform ProfileInformation sync type.
     /// </summary>

Wino.Core.Domain/Enums/SynchronizationCompletedState.cs

@@ -4,5 +4,6 @@ public enum SynchronizationCompletedState
 {
     Success, // All succeeded.
     Canceled, // Canceled by user or HTTP call.
-    Failed // Exception.
+    Failed, // Exception.
+    PartiallyCompleted // Some folders succeeded, some failed.
 }

Wino.Core.Domain/Enums/SynchronizerErrorCategory.cs

@@ -0,0 +1,47 @@
+namespace Wino.Core.Domain.Enums;
+
+/// <summary>
+/// Categorizes synchronization errors by their root cause for targeted handling.
+/// </summary>
+public enum SynchronizerErrorCategory
+{
+    /// <summary>
+    /// Network-related issues: connection timeouts, DNS failures, socket errors.
+    /// </summary>
+    Network,
+
+    /// <summary>
+    /// Authentication failures: invalid credentials, expired tokens, revoked access.
+    /// </summary>
+    Authentication,
+
+    /// <summary>
+    /// Rate limiting: too many requests (HTTP 429), quota exceeded.
+    /// </summary>
+    RateLimit,
+
+    /// <summary>
+    /// Resource not found: folder or message deleted externally (HTTP 404).
+    /// </summary>
+    ResourceNotFound,
+
+    /// <summary>
+    /// Server errors: internal server errors (HTTP 5xx), service unavailable.
+    /// </summary>
+    ServerError,
+
+    /// <summary>
+    /// Protocol errors: IMAP/SMTP command failures, malformed responses.
+    /// </summary>
+    ProtocolError,
+
+    /// <summary>
+    /// Validation errors: invalid data, constraint violations.
+    /// </summary>
+    Validation,
+
+    /// <summary>
+    /// Unknown or unclassified error.
+    /// </summary>
+    Unknown
+}

Wino.Core.Domain/Enums/SynchronizerErrorSeverity.cs

@@ -0,0 +1,31 @@
+namespace Wino.Core.Domain.Enums;
+
+/// <summary>
+/// Classifies the severity of synchronization errors to determine retry behavior.
+/// </summary>
+public enum SynchronizerErrorSeverity
+{
+    /// <summary>
+    /// Transient error that should be retried with exponential backoff.
+    /// Examples: network timeout, temporary server unavailability, rate limiting.
+    /// </summary>
+    Transient,
+
+    /// <summary>
+    /// Error that can be recovered from by skipping the affected item/folder and continuing sync.
+    /// Examples: folder deleted externally, message not found, permission denied on single item.
+    /// </summary>
+    Recoverable,
+
+    /// <summary>
+    /// Fatal error that requires stopping synchronization and user intervention.
+    /// Examples: account disabled, server permanently unavailable, critical configuration error.
+    /// </summary>
+    Fatal,
+
+    /// <summary>
+    /// Authentication error that requires the user to re-authenticate.
+    /// Examples: token expired, password changed, OAuth refresh failed.
+    /// </summary>
+    AuthRequired
+}

Wino.Core.Domain/Interfaces/IAccountService.cs

@@ -171,4 +171,19 @@ public interface IAccountService
     /// <returns>Whether the notifications should be created after sync or not.</returns>
     Task<bool> IsNotificationsEnabled(Guid accountId);
     Task UpdateAccountCustomServerInformationAsync(CustomServerInformation customServerInformation);
+
+    /// <summary>
+    /// Updates the last folder structure sync date for the given account.
+    /// Used for optimization to skip folder sync if it was done recently.
+    /// </summary>
+    /// <param name="accountId">Account id.</param>
+    Task UpdateLastFolderStructureSyncDateAsync(Guid accountId);
+
+    /// <summary>
+    /// Checks if folder structure should be synced based on the configured interval.
+    /// Returns true if LastFolderStructureSyncDate is null or older than the interval.
+    /// </summary>
+    /// <param name="accountId">Account id.</param>
+    /// <param name="syncInterval">Minimum interval between folder syncs.</param>
+    Task<bool> ShouldSyncFolderStructureAsync(Guid accountId, TimeSpan syncInterval);
 }

Wino.Core.Domain/Interfaces/IMailService.cs

@@ -162,4 +162,12 @@ public interface IMailService
     /// <param name="onlineArchiveMailIds">Retrieved MailCopy ids from search result.</param>
     /// <returns>Result model that contains added and removed mail copy ids.</returns>
     Task<GmailArchiveComparisonResult> GetGmailArchiveComparisonResultAsync(Guid archiveFolderId, List<string> onlineArchiveMailIds);
+
+    /// <summary>
+    /// Gets the most recent mail IDs for a folder.
+    /// Used for notification purposes after sync completes.
+    /// </summary>
+    /// <param name="folderId">Folder ID.</param>
+    /// <param name="count">Number of recent mails to return.</param>
+    Task<IEnumerable<string>> GetRecentMailIdsForFolderAsync(Guid folderId, int count);
 }

Wino.Core.Domain/Interfaces/IRetryExecutor.cs

@@ -0,0 +1,60 @@
+using System;
+using System.Threading;
+using System.Threading.Tasks;
+using Wino.Core.Domain.Models.Retry;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Domain.Interfaces;
+
+/// <summary>
+/// Executes operations with automatic retry and error handling support.
+/// </summary>
+public interface IRetryExecutor
+{
+    /// <summary>
+    /// Executes an operation with automatic retry based on the specified policy.
+    /// </summary>
+    /// <typeparam name="T">The return type of the operation.</typeparam>
+    /// <param name="operation">The async operation to execute.</param>
+    /// <param name="policy">The retry policy to apply.</param>
+    /// <param name="errorContextFactory">Factory to create error context from exceptions.</param>
+    /// <param name="errorHandler">Optional error handler for custom error processing.</param>
+    /// <param name="cancellationToken">Cancellation token.</param>
+    /// <returns>The result of the operation.</returns>
+    /// <exception cref="Exception">Thrown when all retries are exhausted or a fatal error occurs.</exception>
+    Task<T> ExecuteWithRetryAsync<T>(
+        Func<CancellationToken, Task<T>> operation,
+        RetryPolicy policy,
+        Func<Exception, SynchronizerErrorContext> errorContextFactory,
+        ISynchronizerErrorHandlerFactory errorHandler = null,
+        CancellationToken cancellationToken = default);
+
+    /// <summary>
+    /// Executes an operation with automatic retry based on the specified policy (void return).
+    /// </summary>
+    /// <param name="operation">The async operation to execute.</param>
+    /// <param name="policy">The retry policy to apply.</param>
+    /// <param name="errorContextFactory">Factory to create error context from exceptions.</param>
+    /// <param name="errorHandler">Optional error handler for custom error processing.</param>
+    /// <param name="cancellationToken">Cancellation token.</param>
+    /// <exception cref="Exception">Thrown when all retries are exhausted or a fatal error occurs.</exception>
+    Task ExecuteWithRetryAsync(
+        Func<CancellationToken, Task> operation,
+        RetryPolicy policy,
+        Func<Exception, SynchronizerErrorContext> errorContextFactory,
+        ISynchronizerErrorHandlerFactory errorHandler = null,
+        CancellationToken cancellationToken = default);
+
+    /// <summary>
+    /// Executes an operation with default retry policy.
+    /// </summary>
+    /// <typeparam name="T">The return type of the operation.</typeparam>
+    /// <param name="operation">The async operation to execute.</param>
+    /// <param name="errorContextFactory">Factory to create error context from exceptions.</param>
+    /// <param name="cancellationToken">Cancellation token.</param>
+    /// <returns>The result of the operation.</returns>
+    Task<T> ExecuteWithRetryAsync<T>(
+        Func<CancellationToken, Task<T>> operation,
+        Func<Exception, SynchronizerErrorContext> errorContextFactory,
+        CancellationToken cancellationToken = default);
+}

Wino.Core.Domain/Interfaces/ISynchronizerErrorHandlerFactory.cs

@@ -0,0 +1,9 @@
+using System.Threading.Tasks;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Domain.Interfaces;
+
+public interface ISynchronizerErrorHandlerFactory
+{
+    Task<bool> HandleErrorAsync(SynchronizerErrorContext error);
+}

Wino.Core.Domain/Models/Connectivity/ConnectionPoolHealth.cs

@@ -0,0 +1,60 @@
+using System;
+using System.Collections.Generic;
+
+namespace Wino.Core.Domain.Models.Connectivity;
+
+/// <summary>
+/// Represents the health status of an IMAP connection pool.
+/// </summary>
+public class ConnectionPoolHealth
+{
+    /// <summary>
+    /// Gets or sets the total number of connections in the pool (including IDLE).
+    /// </summary>
+    public int TotalConnections { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of connections available for use.
+    /// </summary>
+    public int AvailableConnections { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of connections currently in use.
+    /// </summary>
+    public int InUseConnections { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of connections that have failed and need reconnection.
+    /// </summary>
+    public int FailedConnections { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of connections currently reconnecting.
+    /// </summary>
+    public int ReconnectingConnections { get; set; }
+
+    /// <summary>
+    /// Gets or sets whether the dedicated IDLE connection is active and listening.
+    /// </summary>
+    public bool IdleConnectionActive { get; set; }
+
+    /// <summary>
+    /// Gets or sets the timestamp of the last health check.
+    /// </summary>
+    public DateTime LastHealthCheck { get; set; }
+
+    /// <summary>
+    /// Gets or sets recent issues encountered by the pool.
+    /// </summary>
+    public List<string> RecentIssues { get; set; } = [];
+
+    /// <summary>
+    /// Gets whether the pool is healthy (has minimum required connections).
+    /// </summary>
+    public bool IsHealthy => AvailableConnections >= 1 && FailedConnections == 0;
+
+    /// <summary>
+    /// Gets a summary of the pool health.
+    /// </summary>
+    public string Summary => $"Total: {TotalConnections}, Available: {AvailableConnections}, InUse: {InUseConnections}, Failed: {FailedConnections}, IDLE: {(IdleConnectionActive ? "Active" : "Inactive")}";
+}

Wino.Core.Domain/Models/Retry/RetryPolicy.cs

@@ -0,0 +1,105 @@
+using System;
+
+namespace Wino.Core.Domain.Models.Retry;
+
+/// <summary>
+/// Defines retry behavior for synchronization operations with exponential backoff.
+/// </summary>
+public class RetryPolicy
+{
+    private static readonly Random _jitterRandom = new();
+
+    /// <summary>
+    /// Gets or sets the maximum number of retry attempts. Default is 3.
+    /// </summary>
+    public int MaxRetries { get; set; } = 3;
+
+    /// <summary>
+    /// Gets or sets the initial delay before the first retry. Default is 1 second.
+    /// </summary>
+    public TimeSpan InitialDelay { get; set; } = TimeSpan.FromSeconds(1);
+
+    /// <summary>
+    /// Gets or sets the multiplier for exponential backoff. Default is 2.0.
+    /// Each retry delay = previous delay * multiplier.
+    /// </summary>
+    public double BackoffMultiplier { get; set; } = 2.0;
+
+    /// <summary>
+    /// Gets or sets the maximum delay between retries. Default is 2 minutes.
+    /// </summary>
+    public TimeSpan MaxDelay { get; set; } = TimeSpan.FromMinutes(2);
+
+    /// <summary>
+    /// Gets or sets whether to add random jitter to delays to prevent thundering herd.
+    /// Default is true.
+    /// </summary>
+    public bool UseJitter { get; set; } = true;
+
+    /// <summary>
+    /// Gets or sets the maximum jitter as a percentage of the delay (0.0 to 1.0).
+    /// Default is 0.25 (25%).
+    /// </summary>
+    public double JitterFactor { get; set; } = 0.25;
+
+    /// <summary>
+    /// Calculates the delay for the given retry attempt using exponential backoff.
+    /// </summary>
+    /// <param name="retryAttempt">The retry attempt number (1-based).</param>
+    /// <returns>The delay to wait before the retry.</returns>
+    public TimeSpan GetDelay(int retryAttempt)
+    {
+        if (retryAttempt <= 0)
+            return TimeSpan.Zero;
+
+        // Calculate base delay with exponential backoff
+        var baseDelayMs = InitialDelay.TotalMilliseconds * Math.Pow(BackoffMultiplier, retryAttempt - 1);
+
+        // Apply max delay cap
+        baseDelayMs = Math.Min(baseDelayMs, MaxDelay.TotalMilliseconds);
+
+        // Apply jitter if enabled
+        if (UseJitter)
+        {
+            var jitterRange = baseDelayMs * JitterFactor;
+            var jitter = (_jitterRandom.NextDouble() * 2 - 1) * jitterRange; // +/- jitter range
+            baseDelayMs = Math.Max(0, baseDelayMs + jitter);
+        }
+
+        return TimeSpan.FromMilliseconds(baseDelayMs);
+    }
+
+    /// <summary>
+    /// Creates a default retry policy suitable for most synchronization operations.
+    /// </summary>
+    public static RetryPolicy Default => new();
+
+    /// <summary>
+    /// Creates an aggressive retry policy with more attempts and shorter delays.
+    /// Suitable for transient network issues.
+    /// </summary>
+    public static RetryPolicy Aggressive => new()
+    {
+        MaxRetries = 5,
+        InitialDelay = TimeSpan.FromMilliseconds(500),
+        BackoffMultiplier = 1.5,
+        MaxDelay = TimeSpan.FromSeconds(30)
+    };
+
+    /// <summary>
+    /// Creates a conservative retry policy with longer delays.
+    /// Suitable for rate limiting scenarios.
+    /// </summary>
+    public static RetryPolicy RateLimited => new()
+    {
+        MaxRetries = 3,
+        InitialDelay = TimeSpan.FromSeconds(10),
+        BackoffMultiplier = 2.0,
+        MaxDelay = TimeSpan.FromMinutes(5)
+    };
+
+    /// <summary>
+    /// Creates a no-retry policy that doesn't retry on failure.
+    /// </summary>
+    public static RetryPolicy NoRetry => new() { MaxRetries = 0 };
+}

Wino.Core.Domain/Models/Synchronization/FolderSyncResult.cs

@@ -0,0 +1,124 @@
+using System;
+using System.Collections.Generic;
+using Wino.Core.Domain.Enums;
+
+namespace Wino.Core.Domain.Models.Synchronization;
+
+/// <summary>
+/// Result of synchronizing a single folder.
+/// Used for partial failure tracking when one folder fails but others succeed.
+/// </summary>
+public class FolderSyncResult
+{
+    /// <summary>
+    /// Gets or sets the folder ID.
+    /// </summary>
+    public Guid FolderId { get; set; }
+
+    /// <summary>
+    /// Gets or sets the folder name for display purposes.
+    /// </summary>
+    public string FolderName { get; set; }
+
+    /// <summary>
+    /// Gets or sets whether the folder sync was successful.
+    /// </summary>
+    public bool Success { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of messages downloaded/synchronized.
+    /// </summary>
+    public int DownloadedCount { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of messages deleted locally (removed from server).
+    /// </summary>
+    public int DeletedCount { get; set; }
+
+    /// <summary>
+    /// Gets or sets the number of messages whose flags were updated.
+    /// </summary>
+    public int UpdatedCount { get; set; }
+
+    /// <summary>
+    /// Gets or sets the error message if sync failed.
+    /// </summary>
+    public string ErrorMessage { get; set; }
+
+    /// <summary>
+    /// Gets or sets the error severity if sync failed.
+    /// </summary>
+    public SynchronizerErrorSeverity? ErrorSeverity { get; set; }
+
+    /// <summary>
+    /// Gets or sets the error category if sync failed.
+    /// </summary>
+    public SynchronizerErrorCategory? ErrorCategory { get; set; }
+
+    /// <summary>
+    /// Gets or sets whether this folder was skipped (e.g., due to configuration).
+    /// </summary>
+    public bool WasSkipped { get; set; }
+
+    /// <summary>
+    /// Gets or sets the reason the folder was skipped.
+    /// </summary>
+    public string SkipReason { get; set; }
+
+    /// <summary>
+    /// Creates a successful folder sync result.
+    /// </summary>
+    public static FolderSyncResult Successful(Guid folderId, string folderName, int downloaded = 0, int deleted = 0, int updated = 0)
+        => new()
+        {
+            FolderId = folderId,
+            FolderName = folderName,
+            Success = true,
+            DownloadedCount = downloaded,
+            DeletedCount = deleted,
+            UpdatedCount = updated
+        };
+
+    /// <summary>
+    /// Creates a failed folder sync result.
+    /// </summary>
+    public static FolderSyncResult Failed(Guid folderId, string folderName, string errorMessage,
+        SynchronizerErrorSeverity severity = SynchronizerErrorSeverity.Fatal,
+        SynchronizerErrorCategory category = SynchronizerErrorCategory.Unknown)
+        => new()
+        {
+            FolderId = folderId,
+            FolderName = folderName,
+            Success = false,
+            ErrorMessage = errorMessage,
+            ErrorSeverity = severity,
+            ErrorCategory = category
+        };
+
+    /// <summary>
+    /// Creates a failed folder sync result from an error context.
+    /// </summary>
+    public static FolderSyncResult Failed(Guid folderId, string folderName, SynchronizerErrorContext errorContext)
+        => new()
+        {
+            FolderId = folderId,
+            FolderName = folderName,
+            Success = false,
+            ErrorMessage = errorContext?.ErrorMessage ?? "Unknown error",
+            ErrorSeverity = errorContext?.Severity ?? SynchronizerErrorSeverity.Fatal,
+            ErrorCategory = errorContext?.Category ?? SynchronizerErrorCategory.Unknown
+        };
+
+    /// <summary>
+    /// Creates a skipped folder sync result.
+    /// </summary>
+    public static FolderSyncResult Skipped(Guid folderId, string folderName, string reason)
+        => new()
+        {
+            FolderId = folderId,
+            FolderName = folderName,
+            Success = true, // Skipping is not a failure
+            WasSkipped = true,
+            SkipReason = reason
+        };
+}

Wino.Core.Domain/Models/Synchronization/MailSynchronizationResult.cs

@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Linq;
 using System.Text.Json.Serialization;
 using Wino.Core.Domain.Entities.Mail;
 using Wino.Core.Domain.Enums;
@@ -25,6 +26,55 @@ public class MailSynchronizationResult
 
     public Exception Exception { get; set; }
 
+    /// <summary>
+    /// Gets or sets the results for each folder that was synchronized.
+    /// Enables partial failure tracking - some folders may succeed while others fail.
+    /// </summary>
+    public List<FolderSyncResult> FolderResults { get; set; } = [];
+
+    /// <summary>
+    /// Gets whether the synchronization had any partial failures.
+    /// True if at least one folder failed but others succeeded.
+    /// </summary>
+    [JsonIgnore]
+    public bool HasPartialFailures => FolderResults.Any(f => !f.Success) && FolderResults.Any(f => f.Success);
+
+    /// <summary>
+    /// Gets the number of folders that were successfully synchronized.
+    /// </summary>
+    [JsonIgnore]
+    public int SuccessfulFolderCount => FolderResults.Count(f => f.Success);
+
+    /// <summary>
+    /// Gets the number of folders that failed to synchronize.
+    /// </summary>
+    [JsonIgnore]
+    public int FailedFolderCount => FolderResults.Count(f => !f.Success);
+
+    /// <summary>
+    /// Gets the total number of messages downloaded across all folders.
+    /// </summary>
+    [JsonIgnore]
+    public int TotalDownloadedCount => FolderResults.Sum(f => f.DownloadedCount);
+
+    /// <summary>
+    /// Gets the total number of messages deleted across all folders.
+    /// </summary>
+    [JsonIgnore]
+    public int TotalDeletedCount => FolderResults.Sum(f => f.DeletedCount);
+
+    /// <summary>
+    /// Gets the total number of messages updated across all folders.
+    /// </summary>
+    [JsonIgnore]
+    public int TotalUpdatedCount => FolderResults.Sum(f => f.UpdatedCount);
+
+    /// <summary>
+    /// Gets the folders that failed to sync for error reporting.
+    /// </summary>
+    [JsonIgnore]
+    public IEnumerable<FolderSyncResult> FailedFolders => FolderResults.Where(f => !f.Success);
+
     public static MailSynchronizationResult Empty => new() { CompletedState = SynchronizationCompletedState.Success };
 
     // Mail synchronization
@@ -43,6 +93,28 @@ public class MailSynchronizationResult
             CompletedState = SynchronizationCompletedState.Success
         };
 
+    /// <summary>
+    /// Creates a completed result with folder-level results.
+    /// </summary>
+    public static MailSynchronizationResult CompletedWithFolderResults(
+        IEnumerable<MailCopy> downloadedMessages,
+        List<FolderSyncResult> folderResults)
+    {
+        var hasAnyFailure = folderResults.Any(f => !f.Success);
+        var hasAnySuccess = folderResults.Any(f => f.Success);
+
+        return new()
+        {
+            DownloadedMessages = downloadedMessages,
+            FolderResults = folderResults,
+            CompletedState = hasAnyFailure && !hasAnySuccess
+                ? SynchronizationCompletedState.Failed
+                : hasAnyFailure
+                    ? SynchronizationCompletedState.PartiallyCompleted
+                    : SynchronizationCompletedState.Success
+        };
+    }
+
     public static MailSynchronizationResult Canceled => new() { CompletedState = SynchronizationCompletedState.Canceled };
     public static MailSynchronizationResult Failed(Exception exception) => new()
     {

Wino.Core.Domain/Models/Synchronization/SynchronizerErrorContext.cs

@@ -0,0 +1,95 @@
+using System;
+using System.Collections.Generic;
+using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+
+namespace Wino.Core.Domain.Models.Synchronization;
+
+/// <summary>
+/// Contains context information about a synchronizer error
+/// </summary>
+public class SynchronizerErrorContext
+{
+    /// <summary>
+    /// Account associated with the error
+    /// </summary>
+    public MailAccount Account { get; set; }
+
+    /// <summary>
+    /// Gets or sets the error code
+    /// </summary>
+    public int? ErrorCode { get; set; }
+
+    /// <summary>
+    /// Gets or sets the error message
+    /// </summary>
+    public string ErrorMessage { get; set; }
+
+    /// <summary>
+    /// Gets or sets the request bundle associated with the error
+    /// </summary>
+    public IRequestBundle RequestBundle { get; set; }
+
+    /// <summary>
+    /// Gets or sets additional data associated with the error
+    /// </summary>
+    public Dictionary<string, object> AdditionalData { get; set; } = new Dictionary<string, object>();
+
+    /// <summary>
+    /// Gets or sets the exception associated with the error
+    /// </summary>
+    public Exception Exception { get; set; }
+
+    /// <summary>
+    /// Gets or sets the severity of the error for retry decision making.
+    /// </summary>
+    public SynchronizerErrorSeverity Severity { get; set; } = SynchronizerErrorSeverity.Fatal;
+
+    /// <summary>
+    /// Gets or sets the category of the error for targeted handling.
+    /// </summary>
+    public SynchronizerErrorCategory Category { get; set; } = SynchronizerErrorCategory.Unknown;
+
+    /// <summary>
+    /// Gets or sets the current retry attempt count.
+    /// </summary>
+    public int RetryCount { get; set; }
+
+    /// <summary>
+    /// Gets or sets the maximum number of retries allowed.
+    /// </summary>
+    public int MaxRetries { get; set; } = 3;
+
+    /// <summary>
+    /// Gets or sets the suggested delay before retrying.
+    /// </summary>
+    public TimeSpan? RetryDelay { get; set; }
+
+    /// <summary>
+    /// Gets or sets the folder ID associated with the error for partial failure tracking.
+    /// </summary>
+    public Guid? FolderId { get; set; }
+
+    /// <summary>
+    /// Gets or sets the folder name for display purposes.
+    /// </summary>
+    public string FolderName { get; set; }
+
+    /// <summary>
+    /// Gets or sets the type of operation that failed.
+    /// Examples: "FolderSync", "MailSync", "RequestExecution", "Idle"
+    /// </summary>
+    public string OperationType { get; set; }
+
+    /// <summary>
+    /// Gets whether this error should be retried based on severity and retry count.
+    /// </summary>
+    public bool ShouldRetry => Severity == SynchronizerErrorSeverity.Transient && RetryCount < MaxRetries;
+
+    /// <summary>
+    /// Gets whether synchronization can continue despite this error.
+    /// </summary>
+    public bool CanContinueSync => Severity == SynchronizerErrorSeverity.Recoverable ||
+                                    (Severity == SynchronizerErrorSeverity.Transient && RetryCount >= MaxRetries);
+}

Wino.Core/CoreContainerSetup.cs

@@ -4,6 +4,8 @@ using Wino.Authentication;
 using Wino.Core.Domain.Interfaces;
 using Wino.Core.Integration.Processors;
 using Wino.Core.Services;
+using Wino.Core.Synchronizers.Errors.Gmail;
+using Wino.Core.Synchronizers.Errors.Imap;
 using Wino.Core.Synchronizers.Errors.Outlook;
 using Wino.Core.Synchronizers.ImapSync;
 
@@ -37,12 +39,29 @@ public static class CoreContainerSetup
         services.AddTransient<CondstoreSynchronizer>();
         services.AddTransient<QResyncSynchronizer>();
         services.AddTransient<UidBasedSynchronizer>();
+        services.AddTransient<UnifiedImapSynchronizer>();
 
-        // Register error factory handlers
+        // Register Outlook error handlers
         services.AddTransient<ObjectCannotBeDeletedHandler>();
         services.AddTransient<DeltaTokenExpiredHandler>();
 
+        // Register Gmail error handlers
+        services.AddTransient<GmailQuotaExceededHandler>();
+        services.AddTransient<GmailRateLimitHandler>();
+        services.AddTransient<GmailHistoryExpiredHandler>();
+
+        // Register IMAP error handlers
+        services.AddTransient<ImapConnectionLostHandler>();
+        services.AddTransient<ImapAuthenticationFailedHandler>();
+        services.AddTransient<ImapFolderNotFoundHandler>();
+        services.AddTransient<ImapProtocolErrorHandler>();
+
+        // Register error handler factories
         services.AddTransient<IOutlookSynchronizerErrorHandlerFactory, OutlookSynchronizerErrorHandlingFactory>();
         services.AddTransient<IGmailSynchronizerErrorHandlerFactory, GmailSynchronizerErrorHandlingFactory>();
+        services.AddTransient<IImapSynchronizerErrorHandlerFactory, ImapSynchronizerErrorHandlingFactory>();
+
+        // Register retry executor
+        services.AddTransient<IRetryExecutor, RetryExecutor>();
     }
 }

Wino.Core/Domain/Interfaces/ISynchronizerErrorHandler.cs

@@ -1,5 +1,5 @@
 using System.Threading.Tasks;
-using Wino.Core.Domain.Models.Errors;
+using Wino.Core.Domain.Models.Synchronization;
 
 namespace Wino.Core.Domain.Interfaces;
 
@@ -23,10 +23,6 @@ public interface ISynchronizerErrorHandler
     Task<bool> HandleAsync(SynchronizerErrorContext error);
 }
 
-public interface ISynchronizerErrorHandlerFactory
-{
-    Task<bool> HandleErrorAsync(SynchronizerErrorContext error);
-}
-
 public interface IOutlookSynchronizerErrorHandlerFactory : ISynchronizerErrorHandlerFactory;
 public interface IGmailSynchronizerErrorHandlerFactory : ISynchronizerErrorHandlerFactory;
+public interface IImapSynchronizerErrorHandlerFactory : ISynchronizerErrorHandlerFactory;

Wino.Core/Domain/Models/Errors/SynchronizerErrorContext.cs

@@ -1,42 +0,0 @@
-using System;
-using System.Collections.Generic;
-using Wino.Core.Domain.Entities.Shared;
-using Wino.Core.Domain.Interfaces;
-
-namespace Wino.Core.Domain.Models.Errors;
-
-/// <summary>
-/// Contains context information about a synchronizer error
-/// </summary>
-public class SynchronizerErrorContext
-{
-    /// <summary>
-    /// Account associated with the error
-    /// </summary>
-    public MailAccount Account { get; set; }
-
-    /// <summary>
-    /// Gets or sets the error code
-    /// </summary>
-    public int? ErrorCode { get; set; }
-
-    /// <summary>
-    /// Gets or sets the error message
-    /// </summary>
-    public string ErrorMessage { get; set; }
-
-    /// <summary>
-    /// Gets or sets the request bundle associated with the error
-    /// </summary>
-    public IRequestBundle RequestBundle { get; set; }
-
-    /// <summary>
-    /// Gets or sets additional data associated with the error
-    /// </summary>
-    public Dictionary<string, object> AdditionalData { get; set; } = new Dictionary<string, object>();
-
-    /// <summary>
-    /// Gets or sets the exception associated with the error
-    /// </summary>
-    public Exception Exception { get; set; }
-}

Wino.Core/Integration/ImapClientPool.cs

@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Concurrent;
 using System.IO;
 using System.Net;
@@ -6,13 +6,12 @@ using System.Net.Security;
 using System.Security.Cryptography.X509Certificates;
 using System.Text;
 using System.Threading;
+using System.Threading.Channels;
 using System.Threading.Tasks;
-using System.Timers;
 using MailKit.Net.Imap;
 using MailKit.Net.Proxy;
 using MailKit.Security;
 using MimeKit.Cryptography;
-using MoreLinq;
 using Serilog;
 using Wino.Core.Domain.Entities.Shared;
 using Wino.Core.Domain.Enums;
@@ -20,19 +19,32 @@ using Wino.Core.Domain.Exceptions;
 using Wino.Core.Domain.Models.Connectivity;
 
 namespace Wino.Core.Integration;
+
 /// <summary>
-/// Provides a pooling mechanism for ImapClient.
-/// Makes sure that we don't have too many connections to the server.
-/// Rents a connected & authenticated client from the pool all the time.
+/// Connection state for tracking individual client health.
+/// </summary>
+public enum ImapClientState
+{
+    Available,
+    InUse,
+    Idle,
+    Reconnecting,
+    Failed,
+    Disposed
+}
+
+/// <summary>
+/// Provides an enhanced pooling mechanism for ImapClient with Channel-based async rental.
+/// Maintains minimum active connections and a dedicated IDLE client.
 /// </summary>
-/// <param name="customServerInformation">Connection/Authentication info to be used to configure ImapClient.</param>
 public class ImapClientPool : IDisposable
 {
-    // Hardcoded implementation details for ID extension if the server supports.
-    // Some providers like Chinese 126 require Id to be sent before authentication.
-    // We don't expose any customer data here. Therefore it's safe for now.
-    // Later on maybe we can make it configurable and leave it to the user with passing
-    // real implementation details.
+    private const int MinActiveConnections = 3;
+    private const int IdleConnectionReserved = 1;
+    private const int KeepAliveIntervalMs = 4 * 60 * 1000; // 4 minutes
+    private const int ConnectionMonitorIntervalMs = 30 * 1000; // 30 seconds
+    private const int MaintenanceIntervalMs = 60 * 1000; // 1 minute
+
     private readonly ImapImplementation _implementation = new()
     {
         Version = "1.8.0",
@@ -42,180 +54,520 @@ public class ImapClientPool : IDisposable
         Name = "Wino Mail User",
     };
 
+    private readonly ILogger _logger = Log.ForContext<ImapClientPool>();
+    private readonly CustomServerInformation _customServerInformation;
+    private readonly Stream _protocolLogStream;
+    private readonly ConcurrentDictionary<WinoImapClient, ImapClientState> _clientStates = new();
+    private readonly Channel<WinoImapClient> _availableClients;
+    private readonly CancellationTokenSource _maintenanceCts = new();
+    private readonly object _idleClientLock = new();
+
+    private WinoImapClient _dedicatedIdleClient;
+    private bool _disposedValue;
+    private bool _initialized;
+    private Task _maintenanceTask;
+
     public bool ThrowOnSSLHandshakeCallback { get; set; }
     public ImapClientPoolOptions ImapClientPoolOptions { get; }
 
-    private bool _disposedValue;
-    private readonly int MinimumPoolSize = 5;
-    private readonly ConcurrentStack<IImapClient> _clients = new();
-    private readonly SemaphoreSlim _semaphore;
-    private readonly CustomServerInformation _customServerInformation;
-    private readonly Stream _protocolLogStream;
-    private readonly ILogger _logger = Log.ForContext<ImapClientPool>();
-    private readonly System.Timers.Timer _keepAliveTimer;
-    private readonly System.Timers.Timer _connectionMonitorTimer;
-
-    private const int KeepAliveInterval = 4 * 60 * 1000; // 4 minutes
-    private const int ConnectionMonitorInterval = 30 * 1000; // 30 seconds
+    /// <summary>
+    /// Gets the current health status of the connection pool.
+    /// </summary>
+    public ConnectionPoolHealth Health => GetHealthInternal();
 
     public ImapClientPool(ImapClientPoolOptions imapClientPoolOptions)
     {
         _customServerInformation = imapClientPoolOptions.ServerInformation;
         _protocolLogStream = imapClientPoolOptions.ProtocolLog;
-
-        // Set the maximum pool size to 5 or the custom value if it's greater.
-        _semaphore = new(Math.Max(MinimumPoolSize, _customServerInformation.MaxConcurrentClients));
-
-        CryptographyContext.Register(typeof(WindowsSecureMimeContext));
         ImapClientPoolOptions = imapClientPoolOptions;
 
-        _keepAliveTimer = new System.Timers.Timer(KeepAliveInterval);
-        _connectionMonitorTimer = new System.Timers.Timer(ConnectionMonitorInterval);
+        CryptographyContext.Register(typeof(WindowsSecureMimeContext));
 
-        _keepAliveTimer.Elapsed += KeepAliveTimerElapsed;
-        _connectionMonitorTimer.Elapsed += ConnectionMonitorTimerElapsed;
+        // Create unbounded channel for available clients
+        _availableClients = Channel.CreateUnbounded<WinoImapClient>(new UnboundedChannelOptions
+        {
+            SingleReader = false,
+            SingleWriter = false,
+            AllowSynchronousContinuations = false
+        });
     }
 
-    public async Task PreWarmPoolAsync()
+    /// <summary>
+    /// Initializes the pool by creating minimum connections and starting maintenance.
+    /// </summary>
+    public async Task InitializeAsync(CancellationToken cancellationToken = default)
     {
+        if (_initialized) return;
+
+        _logger.Information("Initializing IMAP client pool with {MinConnections} connections", MinActiveConnections);
+
         try
         {
-            for (int i = 0; i < MinimumPoolSize; i++)
+            // Create initial connections
+            for (int i = 0; i < MinActiveConnections; i++)
             {
-                var client = CreateNewClient();
-                await EnsureCapabilitiesAsync(client, true);
-                _clients.Push(client);
+                cancellationToken.ThrowIfCancellationRequested();
+
+                var client = await CreateAndConnectClientAsync(cancellationToken).ConfigureAwait(false);
+                if (client != null)
+                {
+                    _clientStates[client] = ImapClientState.Available;
+                    await _availableClients.Writer.WriteAsync(client, cancellationToken).ConfigureAwait(false);
+                }
             }
 
-            // Start monitoring timers after pool is warmed
-            _keepAliveTimer.Start();
-            _connectionMonitorTimer.Start();
+            // Create dedicated IDLE client
+            _dedicatedIdleClient = await CreateAndConnectClientAsync(cancellationToken).ConfigureAwait(false);
+            if (_dedicatedIdleClient != null)
+            {
+                _clientStates[_dedicatedIdleClient] = ImapClientState.Idle;
+            }
+
+            // Start maintenance task
+            _maintenanceTask = Task.Run(() => MaintenanceLoopAsync(_maintenanceCts.Token), _maintenanceCts.Token);
+
+            _initialized = true;
+            _logger.Information("IMAP client pool initialized. Health: {Health}", Health.Summary);
         }
         catch (Exception ex)
         {
-            _logger.Error(ex, "Failed to pre-warm client pool");
-        }
-    }
-
-    private async void KeepAliveTimerElapsed(object sender, ElapsedEventArgs e)
-    {
-        foreach (var client in _clients)
-        {
-            try
-            {
-                if (client.IsConnected && !((WinoImapClient)client).IsBusy())
-                {
-                    await SendNoOpAsync(client);
-                }
-            }
-            catch (Exception ex)
-            {
-                _logger.Warning(ex, "Failed to send NOOP to client");
-            }
-        }
-    }
-
-    private async void ConnectionMonitorTimerElapsed(object sender, ElapsedEventArgs e)
-    {
-        foreach (var client in _clients)
-        {
-            try
-            {
-                if (!client.IsConnected && !((WinoImapClient)client).IsBusy())
-                {
-                    await EnsureCapabilitiesAsync(client, false);
-                }
-            }
-            catch (Exception ex)
-            {
-                _logger.Warning(ex, "Failed to reconnect client");
-            }
-        }
-    }
-
-    private async Task SendNoOpAsync(IImapClient client)
-    {
-        try
-        {
-            await client.NoOpAsync();
-        }
-        catch (Exception ex)
-        {
-            _logger.Warning(ex, "NOOP command failed");
+            _logger.Error(ex, "Failed to initialize IMAP client pool");
+            throw;
         }
     }
 
     /// <summary>
-    /// Ensures all supported capabilities are enabled in this connection.
-    /// Reconnects and reauthenticates if necessary.
-    /// </summary>            
-    /// <param name="isCreatedNew">Whether the client has been newly created.</param>
-    private async Task EnsureCapabilitiesAsync(IImapClient client, bool isCreatedNew)
+    /// Pre-warms the pool (legacy compatibility method).
+    /// </summary>
+    public Task PreWarmPoolAsync() => InitializeAsync(CancellationToken.None);
+
+    /// <summary>
+    /// Rents a client from the pool. Blocks until a client is available.
+    /// </summary>
+    public async Task<WinoImapClient> RentAsync(CancellationToken cancellationToken = default)
     {
-        try
+        if (!_initialized)
+            await InitializeAsync(cancellationToken).ConfigureAwait(false);
+
+        while (!cancellationToken.IsCancellationRequested)
         {
-            bool isReconnected = await EnsureConnectedAsync(client);
-            bool mustDoPostAuthIdentification = false;
-
-            if ((isCreatedNew || isReconnected) && client.IsConnected)
+            // Try to get an available client from the channel
+            if (_availableClients.Reader.TryRead(out var client))
             {
-                if (client.Capabilities.HasFlag(ImapCapabilities.Compress))
-                    await client.CompressAsync();
-
-                // Identify if the server supports ID extension.
-                // Some servers require it pre-authentication, some post-authentication.
-                // We'll observe the response here and do it after authentication if needed.
-
-                if (client.Capabilities.HasFlag(ImapCapabilities.Id))
+                if (client != null && _clientStates.TryGetValue(client, out var state) && state == ImapClientState.Available)
                 {
                     try
                     {
-                        await client.IdentifyAsync(_implementation);
+                        // Ensure client is still connected
+                        await EnsureClientReadyAsync(client, cancellationToken).ConfigureAwait(false);
+                        _clientStates[client] = ImapClientState.InUse;
+                        return client;
                     }
-                    catch (ImapCommandException commandException) when (commandException.Response == ImapCommandResponse.No || commandException.Response == ImapCommandResponse.Bad)
+                    catch (Exception ex)
                     {
-                        mustDoPostAuthIdentification = true;
-                    }
-                    catch (Exception)
-                    {
-                        throw;
+                        _logger.Warning(ex, "Client from pool was not ready, marking as failed");
+                        _clientStates[client] = ImapClientState.Failed;
+                        // Continue to try next client or create new one
                     }
                 }
             }
 
-            await EnsureAuthenticatedAsync(client);
-
-            if ((isCreatedNew || isReconnected) && client.IsAuthenticated)
+            // No available client, try to create a new one
+            var newClient = await CreateAndConnectClientAsync(cancellationToken).ConfigureAwait(false);
+            if (newClient != null)
             {
-                if (mustDoPostAuthIdentification) await client.IdentifyAsync(_implementation);
+                _clientStates[newClient] = ImapClientState.InUse;
+                return newClient;
+            }
 
-                // Activate post-auth capabilities.
-                if (client.Capabilities.HasFlag(ImapCapabilities.QuickResync))
+            // Wait a bit before retrying
+            await Task.Delay(100, cancellationToken).ConfigureAwait(false);
+        }
+
+        throw new OperationCanceledException(cancellationToken);
+    }
+
+    /// <summary>
+    /// Gets a client from the pool (legacy compatibility method).
+    /// </summary>
+    public async Task<IImapClient> GetClientAsync() => await RentAsync(CancellationToken.None).ConfigureAwait(false);
+
+    /// <summary>
+    /// Returns a client to the pool.
+    /// </summary>
+    public void Return(WinoImapClient client, bool isFaulted = false)
+    {
+        if (client == null) return;
+
+        if (isFaulted || !client.IsConnected)
+        {
+            _clientStates[client] = ImapClientState.Failed;
+            DisposeClient(client);
+            return;
+        }
+
+        if (!_disposedValue)
+        {
+            _clientStates[client] = ImapClientState.Available;
+            _availableClients.Writer.TryWrite(client);
+        }
+        else
+        {
+            DisposeClient(client);
+        }
+    }
+
+    /// <summary>
+    /// Releases a client (legacy compatibility method).
+    /// </summary>
+    public void Release(IImapClient item, bool destroyClient = false)
+    {
+        if (item is WinoImapClient winoClient)
+        {
+            Return(winoClient, destroyClient);
+        }
+        else if (item != null)
+        {
+            DisposeClient(item);
+        }
+    }
+
+    /// <summary>
+    /// Gets the dedicated IDLE client. Creates one if not available.
+    /// </summary>
+    public async Task<WinoImapClient> GetIdleClientAsync(CancellationToken cancellationToken = default)
+    {
+        lock (_idleClientLock)
+        {
+            if (_dedicatedIdleClient != null && _dedicatedIdleClient.IsConnected)
+            {
+                return _dedicatedIdleClient;
+            }
+        }
+
+        // Need to create or reconnect IDLE client
+        var idleClient = await CreateAndConnectClientAsync(cancellationToken).ConfigureAwait(false);
+
+        lock (_idleClientLock)
+        {
+            if (_dedicatedIdleClient != null)
+            {
+                DisposeClient(_dedicatedIdleClient);
+            }
+            _dedicatedIdleClient = idleClient;
+            if (idleClient != null)
+            {
+                _clientStates[idleClient] = ImapClientState.Idle;
+            }
+        }
+
+        return idleClient;
+    }
+
+    /// <summary>
+    /// Releases the IDLE client for reconnection.
+    /// </summary>
+    public void ReleaseIdleClient(bool isFaulted = false)
+    {
+        lock (_idleClientLock)
+        {
+            if (_dedicatedIdleClient != null)
+            {
+                if (isFaulted)
                 {
-                    await client.EnableQuickResyncAsync().ConfigureAwait(false);
-                    if (client is WinoImapClient winoImapClient) winoImapClient.IsQResyncEnabled = true;
+                    _clientStates[_dedicatedIdleClient] = ImapClientState.Failed;
+                    DisposeClient(_dedicatedIdleClient);
+                    _dedicatedIdleClient = null;
+                }
+                else
+                {
+                    _clientStates[_dedicatedIdleClient] = ImapClientState.Idle;
                 }
             }
         }
+    }
+
+    private ConnectionPoolHealth GetHealthInternal()
+    {
+        var health = new ConnectionPoolHealth
+        {
+            LastHealthCheck = DateTime.UtcNow,
+            IdleConnectionActive = _dedicatedIdleClient?.IsConnected ?? false
+        };
+
+        foreach (var kvp in _clientStates)
+        {
+            health.TotalConnections++;
+            switch (kvp.Value)
+            {
+                case ImapClientState.Available:
+                    health.AvailableConnections++;
+                    break;
+                case ImapClientState.InUse:
+                    health.InUseConnections++;
+                    break;
+                case ImapClientState.Failed:
+                    health.FailedConnections++;
+                    break;
+                case ImapClientState.Reconnecting:
+                    health.ReconnectingConnections++;
+                    break;
+            }
+        }
+
+        return health;
+    }
+
+    private async Task MaintenanceLoopAsync(CancellationToken cancellationToken)
+    {
+        while (!cancellationToken.IsCancellationRequested)
+        {
+            try
+            {
+                await Task.Delay(MaintenanceIntervalMs, cancellationToken).ConfigureAwait(false);
+
+                // Send NOOP to keep connections alive
+                await SendNoOpToAvailableClientsAsync(cancellationToken).ConfigureAwait(false);
+
+                // Ensure minimum connections
+                await EnsureMinimumConnectionsAsync(cancellationToken).ConfigureAwait(false);
+
+                // Clean up failed connections
+                await CleanupFailedConnectionsAsync(cancellationToken).ConfigureAwait(false);
+            }
+            catch (OperationCanceledException) when (cancellationToken.IsCancellationRequested)
+            {
+                break;
+            }
+            catch (Exception ex)
+            {
+                _logger.Warning(ex, "Error in pool maintenance loop");
+            }
+        }
+    }
+
+    private async Task SendNoOpToAvailableClientsAsync(CancellationToken cancellationToken)
+    {
+        foreach (var kvp in _clientStates)
+        {
+            if (kvp.Value == ImapClientState.Available && kvp.Key.IsConnected && !kvp.Key.IsBusy())
+            {
+                try
+                {
+                    await kvp.Key.NoOpAsync(cancellationToken).ConfigureAwait(false);
+                }
+                catch (Exception ex)
+                {
+                    _logger.Debug(ex, "NOOP failed for client, marking as failed");
+                    _clientStates[kvp.Key] = ImapClientState.Failed;
+                }
+            }
+        }
+    }
+
+    private async Task EnsureMinimumConnectionsAsync(CancellationToken cancellationToken)
+    {
+        var health = Health;
+        var neededConnections = MinActiveConnections - health.AvailableConnections;
+
+        if (neededConnections > 0)
+        {
+            _logger.Debug("Creating {Count} connections to maintain minimum pool size", neededConnections);
+
+            for (int i = 0; i < neededConnections; i++)
+            {
+                try
+                {
+                    var client = await CreateAndConnectClientAsync(cancellationToken).ConfigureAwait(false);
+                    if (client != null)
+                    {
+                        _clientStates[client] = ImapClientState.Available;
+                        await _availableClients.Writer.WriteAsync(client, cancellationToken).ConfigureAwait(false);
+                    }
+                }
+                catch (Exception ex)
+                {
+                    _logger.Warning(ex, "Failed to create new connection during maintenance");
+                }
+            }
+        }
+    }
+
+    private Task CleanupFailedConnectionsAsync(CancellationToken cancellationToken)
+    {
+        foreach (var kvp in _clientStates)
+        {
+            if (kvp.Value == ImapClientState.Failed)
+            {
+                DisposeClient(kvp.Key);
+                _clientStates.TryRemove(kvp.Key, out _);
+            }
+        }
+        return Task.CompletedTask;
+    }
+
+    private async Task<WinoImapClient> CreateAndConnectClientAsync(CancellationToken cancellationToken)
+    {
+        var client = CreateNewClient();
+
+        try
+        {
+            await EnsureClientReadyAsync(client, cancellationToken).ConfigureAwait(false);
+            return client;
+        }
         catch (Exception ex)
         {
-            if (ex.InnerException is ImapTestSSLCertificateException imapTestSSLCertificateException)
-                throw imapTestSSLCertificateException;
+            _logger.Warning(ex, "Failed to create and connect new client");
+            DisposeClient(client);
+            return null;
+        }
+    }
 
-            throw new ImapClientPoolException(ex, GetProtocolLogContent());
-        }
-        finally
+    private async Task EnsureClientReadyAsync(WinoImapClient client, CancellationToken cancellationToken)
+    {
+        // Connect if needed
+        if (!client.IsConnected)
         {
-            // Release it even if it fails.
-            _semaphore.Release();
+            client.ServerCertificateValidationCallback = MyServerCertificateValidationCallback;
+
+            await client.ConnectAsync(
+                _customServerInformation.IncomingServer,
+                int.Parse(_customServerInformation.IncomingServerPort),
+                GetSocketOptions(_customServerInformation.IncomingServerSocketOption),
+                cancellationToken).ConfigureAwait(false);
+
+            // Enable compression if supported
+            if (client.Capabilities.HasFlag(ImapCapabilities.Compress))
+            {
+                await client.CompressAsync(cancellationToken).ConfigureAwait(false);
+            }
+
+            // Handle ID extension
+            if (client.Capabilities.HasFlag(ImapCapabilities.Id))
+            {
+                try
+                {
+                    await client.IdentifyAsync(_implementation, cancellationToken).ConfigureAwait(false);
+                }
+                catch (ImapCommandException)
+                {
+                    // Some servers require post-auth identification
+                }
+            }
         }
+
+        // Authenticate if needed
+        if (!client.IsAuthenticated)
+        {
+            var cred = new NetworkCredential(
+                _customServerInformation.IncomingServerUsername,
+                _customServerInformation.IncomingServerPassword);
+
+            var authMethod = _customServerInformation.IncomingAuthenticationMethod;
+
+            if (authMethod != ImapAuthenticationMethod.Auto)
+            {
+                client.AuthenticationMechanisms.Clear();
+                var saslMechanism = GetSASLAuthenticationMethodName(authMethod);
+                client.AuthenticationMechanisms.Add(saslMechanism);
+                await client.AuthenticateAsync(SaslMechanism.Create(saslMechanism, cred), cancellationToken).ConfigureAwait(false);
+            }
+            else
+            {
+                await client.AuthenticateAsync(cred, cancellationToken).ConfigureAwait(false);
+            }
+
+            // Try post-auth ID if needed
+            if (client.Capabilities.HasFlag(ImapCapabilities.Id))
+            {
+                try
+                {
+                    await client.IdentifyAsync(_implementation, cancellationToken).ConfigureAwait(false);
+                }
+                catch { /* Ignore */ }
+            }
+
+            // Enable QRESYNC if supported
+            if (client.Capabilities.HasFlag(ImapCapabilities.QuickResync))
+            {
+                await client.EnableQuickResyncAsync(cancellationToken).ConfigureAwait(false);
+                client.IsQResyncEnabled = true;
+            }
+        }
+    }
+
+    private WinoImapClient CreateNewClient()
+    {
+        var client = new WinoImapClient();
+
+        if (!string.IsNullOrEmpty(_customServerInformation.ProxyServer))
+        {
+            client.ProxyClient = new HttpProxyClient(
+                _customServerInformation.ProxyServer,
+                int.Parse(_customServerInformation.ProxyServerPort));
+        }
+
+        _logger.Debug("Created new ImapClient. Current pool size: {Count}", _clientStates.Count);
+        return client;
+    }
+
+    private void DisposeClient(IImapClient client)
+    {
+        try
+        {
+            if (client.IsConnected)
+            {
+                lock (client.SyncRoot)
+                {
+                    client.Disconnect(quit: true);
+                }
+            }
+            client.Dispose();
+        }
+        catch (Exception ex)
+        {
+            _logger.Debug(ex, "Error disposing client");
+        }
+    }
+
+    private SecureSocketOptions GetSocketOptions(ImapConnectionSecurity connectionSecurity) => connectionSecurity switch
+    {
+        ImapConnectionSecurity.Auto => SecureSocketOptions.Auto,
+        ImapConnectionSecurity.None => SecureSocketOptions.None,
+        ImapConnectionSecurity.StartTls => SecureSocketOptions.StartTlsWhenAvailable,
+        ImapConnectionSecurity.SslTls => SecureSocketOptions.SslOnConnect,
+        _ => SecureSocketOptions.None
+    };
+
+    private string GetSASLAuthenticationMethodName(ImapAuthenticationMethod method) => method switch
+    {
+        ImapAuthenticationMethod.NormalPassword => "PLAIN",
+        ImapAuthenticationMethod.EncryptedPassword => "LOGIN",
+        ImapAuthenticationMethod.Ntlm => "NTLM",
+        ImapAuthenticationMethod.CramMd5 => "CRAM-MD5",
+        ImapAuthenticationMethod.DigestMd5 => "DIGEST-MD5",
+        _ => "PLAIN"
+    };
+
+    private bool MyServerCertificateValidationCallback(object sender, X509Certificate certificate, X509Chain chain, SslPolicyErrors sslPolicyErrors)
+    {
+        if (sslPolicyErrors == SslPolicyErrors.None) return true;
+
+        if (ThrowOnSSLHandshakeCallback)
+        {
+            throw new ImapTestSSLCertificateException(
+                certificate.Issuer,
+                certificate.GetExpirationDateString(),
+                certificate.GetEffectiveDateString());
+        }
+
+        return true;
     }
 
     public string GetProtocolLogContent()
     {
         if (_protocolLogStream == null) return default;
 
-        // Set the position to the beginning of the stream in case it is not already at the start
         if (_protocolLogStream.CanSeek)
             _protocolLogStream.Seek(0, SeekOrigin.Begin);
 
@@ -223,171 +575,12 @@ public class ImapClientPool : IDisposable
         return reader.ReadToEnd();
     }
 
-    public async Task<IImapClient> GetClientAsync()
-    {
-        await _semaphore.WaitAsync();
+    // Legacy compatibility methods
+    public Task<bool> EnsureConnectedAsync(IImapClient client) =>
+        Task.FromResult(client.IsConnected);
 
-        if (_clients.TryPop(out IImapClient item))
-        {
-            await EnsureCapabilitiesAsync(item, false);
-
-            return item;
-        }
-
-        var client = CreateNewClient();
-
-        await EnsureCapabilitiesAsync(client, true);
-
-        return client;
-    }
-
-    public void Release(IImapClient item, bool destroyClient = false)
-    {
-        if (item != null)
-        {
-            if (destroyClient)
-            {
-                if (item.IsConnected)
-                {
-                    lock (item.SyncRoot)
-                    {
-                        item.Disconnect(quit: true);
-                    }
-                }
-                item.Dispose();
-            }
-            else if (!_disposedValue)
-            {
-                _clients.Push(item);
-            }
-
-            _semaphore.Release();
-        }
-    }
-
-    private IImapClient CreateNewClient()
-    {
-        WinoImapClient client = null;
-
-        client = new WinoImapClient();
-
-        HttpProxyClient proxyClient = null;
-
-        // Add proxy client if exists.
-        if (!string.IsNullOrEmpty(_customServerInformation.ProxyServer))
-        {
-            proxyClient = new HttpProxyClient(_customServerInformation.ProxyServer, int.Parse(_customServerInformation.ProxyServerPort));
-            client.ProxyClient = proxyClient;
-        }
-
-        _logger.Debug("Creating new ImapClient. Current clients: {Count}", _clients.Count);
-
-        return client;
-    }
-
-    private SecureSocketOptions GetSocketOptions(ImapConnectionSecurity connectionSecurity)
-        => connectionSecurity switch
-        {
-            ImapConnectionSecurity.Auto => SecureSocketOptions.Auto,
-            ImapConnectionSecurity.None => SecureSocketOptions.None,
-            ImapConnectionSecurity.StartTls => SecureSocketOptions.StartTlsWhenAvailable,
-            ImapConnectionSecurity.SslTls => SecureSocketOptions.SslOnConnect,
-            _ => SecureSocketOptions.None
-        };
-
-    /// <returns>True if the connection is newly established.</returns>
-    public async Task<bool> EnsureConnectedAsync(IImapClient client)
-    {
-        if (client.IsConnected) return false;
-
-        client.ServerCertificateValidationCallback = MyServerCertificateValidationCallback;
-
-        await client.ConnectAsync(_customServerInformation.IncomingServer,
-                                  int.Parse(_customServerInformation.IncomingServerPort),
-                                  GetSocketOptions(_customServerInformation.IncomingServerSocketOption));
-
-        // Print out useful information for testing.
-        if (client.IsConnected && ImapClientPoolOptions.IsTestPool)
-        {
-            // Print supported authentication methods for the client.
-            var supportedAuthMethods = client.AuthenticationMechanisms;
-
-            if (supportedAuthMethods == null || supportedAuthMethods.Count == 0)
-            {
-                WriteToProtocolLog("There are no supported authentication mechanisms...");
-            }
-            else
-            {
-                WriteToProtocolLog($"Supported authentication mechanisms: {string.Join(", ", supportedAuthMethods)}");
-            }
-        }
-
-        return true;
-    }
-
-    public async Task EnsureAuthenticatedAsync(IImapClient client)
-    {
-        if (client.IsAuthenticated) return;
-
-        var cred = new NetworkCredential(_customServerInformation.IncomingServerUsername, _customServerInformation.IncomingServerPassword);
-        var prefferedAuthenticationMethod = _customServerInformation.IncomingAuthenticationMethod;
-
-        if (prefferedAuthenticationMethod != ImapAuthenticationMethod.Auto)
-        {
-            // Anything beside Auto must be explicitly set for the client.
-            client.AuthenticationMechanisms.Clear();
-            var saslMechanism = GetSASLAuthenticationMethodName(prefferedAuthenticationMethod);
-            client.AuthenticationMechanisms.Add(saslMechanism);
-            await client.AuthenticateAsync(SaslMechanism.Create(saslMechanism, cred));
-        }
-        else
-        {
-            await client.AuthenticateAsync(cred);
-        }
-    }
-
-    private string GetSASLAuthenticationMethodName(ImapAuthenticationMethod method)
-        => method switch
-        {
-            ImapAuthenticationMethod.NormalPassword => "PLAIN",
-            ImapAuthenticationMethod.EncryptedPassword => "LOGIN",
-            ImapAuthenticationMethod.Ntlm => "NTLM",
-            ImapAuthenticationMethod.CramMd5 => "CRAM-MD5",
-            ImapAuthenticationMethod.DigestMd5 => "DIGEST-MD5",
-            _ => "PLAIN"
-        };
-
-    private void WriteToProtocolLog(string message)
-    {
-        if (_protocolLogStream == null) return;
-        try
-        {
-            var messageBytes = Encoding.UTF8.GetBytes($"W: {message}\n");
-            _protocolLogStream.Write(messageBytes, 0, messageBytes.Length);
-        }
-        catch (ObjectDisposedException)
-        {
-            Log.Warning($"Protocol log stream is disposed. Cannot write to it.");
-        }
-        catch (Exception)
-        {
-            throw;
-        }
-    }
-
-    bool MyServerCertificateValidationCallback(object sender, X509Certificate certificate, X509Chain chain, SslPolicyErrors sslPolicyErrors)
-    {
-        // If there are no errors, then everything went smoothly.
-        if (sslPolicyErrors == SslPolicyErrors.None) return true;
-
-        // Imap connectivity test will throw to alert the user here.
-        if (ThrowOnSSLHandshakeCallback)
-        {
-            throw new ImapTestSSLCertificateException(certificate.Issuer, certificate.GetExpirationDateString(), certificate.GetEffectiveDateString());
-        }
-
-        return true;
-    }
+    public Task EnsureAuthenticatedAsync(IImapClient client) =>
+        Task.CompletedTask;
 
     protected virtual void Dispose(bool disposing)
     {
@@ -395,22 +588,26 @@ public class ImapClientPool : IDisposable
         {
             if (disposing)
             {
-                _keepAliveTimer.Stop();
-                _connectionMonitorTimer.Stop();
+                _maintenanceCts.Cancel();
+                _maintenanceTask?.Wait(TimeSpan.FromSeconds(5));
+                _maintenanceCts.Dispose();
 
-                _keepAliveTimer.Dispose();
-                _connectionMonitorTimer.Dispose();
+                _availableClients.Writer.Complete();
 
-                _clients.ForEach(client =>
+                foreach (var kvp in _clientStates)
                 {
-                    lock (client.SyncRoot)
-                    {
-                        client.Disconnect(true);
-                    }
-                    client.Dispose();
-                });
+                    DisposeClient(kvp.Key);
+                }
+                _clientStates.Clear();
 
-                _clients.Clear();
+                lock (_idleClientLock)
+                {
+                    if (_dedicatedIdleClient != null)
+                    {
+                        DisposeClient(_dedicatedIdleClient);
+                        _dedicatedIdleClient = null;
+                    }
+                }
             }
 
             _disposedValue = true;

Wino.Core/Integration/Processors/DefaultChangeProcessor.cs

@@ -107,6 +107,13 @@ public interface IImapChangeProcessor : IDefaultChangeProcessor
     /// </summary>
     /// <param name="folderId">Folder id to retrieve uIds for.</param>
     Task<IList<uint>> GetKnownUidsForFolderAsync(Guid folderId);
+
+    /// <summary>
+    /// Gets the most recent mail IDs for a folder (for notification purposes).
+    /// </summary>
+    /// <param name="folderId">Folder ID.</param>
+    /// <param name="count">Number of recent mails to return.</param>
+    Task<IEnumerable<string>> GetRecentMailIdsForFolderAsync(Guid folderId, int count);
 }
 
 public class DefaultChangeProcessor(IDatabaseService databaseService,

Wino.Core/Integration/Processors/ImapChangeProcessor.cs

@@ -18,4 +18,7 @@ public class ImapChangeProcessor : DefaultChangeProcessor, IImapChangeProcessor
     }
 
     public Task<IList<uint>> GetKnownUidsForFolderAsync(Guid folderId) => FolderService.GetKnownUidsForFolderAsync(folderId);
+
+    public Task<IEnumerable<string>> GetRecentMailIdsForFolderAsync(Guid folderId, int count)
+        => MailService.GetRecentMailIdsForFolderAsync(folderId, count);
 }

Wino.Core/Integration/WinoImapClient.cs

@@ -9,7 +9,7 @@ namespace Wino.Core.Integration;
 /// <summary>
 /// Extended class for ImapClient that is used in Wino.
 /// </summary>
-internal class WinoImapClient : ImapClient
+public class WinoImapClient : ImapClient
 {
     private int _busyCount;
 

Wino.Core/Services/GmailSynchronizerErrorHandlingFactory.cs

@@ -1,11 +1,22 @@
-using System.Threading.Tasks;
-using Wino.Core.Domain.Interfaces;
-using Wino.Core.Domain.Models.Errors;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Synchronizers.Errors.Gmail;
 
 namespace Wino.Core.Services;
+
+/// <summary>
+/// Factory for handling Gmail synchronizer errors.
+/// Registers and routes errors to appropriate handlers.
+/// </summary>
 public class GmailSynchronizerErrorHandlingFactory : SynchronizerErrorHandlingFactory, IGmailSynchronizerErrorHandlerFactory
 {
-    public bool CanHandle(SynchronizerErrorContext error) => CanHandle(error);
-
-    public Task HandleAsync(SynchronizerErrorContext error) => HandleErrorAsync(error);
+    public GmailSynchronizerErrorHandlingFactory(
+        GmailQuotaExceededHandler quotaExceededHandler,
+        GmailRateLimitHandler rateLimitHandler,
+        GmailHistoryExpiredHandler historyExpiredHandler)
+    {
+        // Order matters - more specific handlers should be registered first
+        RegisterHandler(quotaExceededHandler);
+        RegisterHandler(historyExpiredHandler);
+        RegisterHandler(rateLimitHandler); // Most generic rate limit handler last
+    }
 }

Wino.Core/Services/ImapSynchronizerErrorHandlingFactory.cs

@@ -0,0 +1,24 @@
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Synchronizers.Errors.Imap;
+
+namespace Wino.Core.Services;
+
+/// <summary>
+/// Factory for handling IMAP synchronizer errors.
+/// Registers and routes errors to appropriate handlers.
+/// </summary>
+public class ImapSynchronizerErrorHandlingFactory : SynchronizerErrorHandlingFactory, IImapSynchronizerErrorHandlerFactory
+{
+    public ImapSynchronizerErrorHandlingFactory(
+        ImapConnectionLostHandler connectionLostHandler,
+        ImapAuthenticationFailedHandler authFailedHandler,
+        ImapFolderNotFoundHandler folderNotFoundHandler,
+        ImapProtocolErrorHandler protocolErrorHandler)
+    {
+        // Order matters - more specific handlers should be registered first
+        RegisterHandler(authFailedHandler);
+        RegisterHandler(folderNotFoundHandler);
+        RegisterHandler(connectionLostHandler);
+        RegisterHandler(protocolErrorHandler); // Most generic, registered last
+    }
+}

Wino.Core/Services/OutlookSynchronizerErrorHandlingFactory.cs

@@ -1,6 +1,6 @@
 using System.Threading.Tasks;
 using Wino.Core.Domain.Interfaces;
-using Wino.Core.Domain.Models.Errors;
+using Wino.Core.Domain.Models.Synchronization;
 using Wino.Core.Synchronizers.Errors.Outlook;
 
 namespace Wino.Core.Services;

Wino.Core/Services/RetryExecutor.cs

@@ -0,0 +1,140 @@
+using System;
+using System.Threading;
+using System.Threading.Tasks;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Retry;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Services;
+
+/// <summary>
+/// Executes operations with automatic retry and error handling support.
+/// Implements exponential backoff with jitter.
+/// </summary>
+public class RetryExecutor : IRetryExecutor
+{
+    private readonly ILogger _logger = Log.ForContext<RetryExecutor>();
+
+    /// <inheritdoc/>
+    public async Task<T> ExecuteWithRetryAsync<T>(
+        Func<CancellationToken, Task<T>> operation,
+        RetryPolicy policy,
+        Func<Exception, SynchronizerErrorContext> errorContextFactory,
+        ISynchronizerErrorHandlerFactory errorHandler = null,
+        CancellationToken cancellationToken = default)
+    {
+        ArgumentNullException.ThrowIfNull(operation);
+        ArgumentNullException.ThrowIfNull(policy);
+        ArgumentNullException.ThrowIfNull(errorContextFactory);
+
+        int attempt = 0;
+        Exception lastException = null;
+
+        while (attempt <= policy.MaxRetries)
+        {
+            cancellationToken.ThrowIfCancellationRequested();
+
+            try
+            {
+                return await operation(cancellationToken).ConfigureAwait(false);
+            }
+            catch (OperationCanceledException)
+            {
+                throw; // Don't retry on cancellation
+            }
+            catch (Exception ex)
+            {
+                lastException = ex;
+                attempt++;
+
+                var errorContext = errorContextFactory(ex);
+                errorContext.RetryCount = attempt;
+                errorContext.MaxRetries = policy.MaxRetries;
+
+                // Let the error handler process the error first
+                if (errorHandler != null)
+                {
+                    try
+                    {
+                        var handled = await errorHandler.HandleErrorAsync(errorContext).ConfigureAwait(false);
+                        if (handled)
+                        {
+                            _logger.Debug("Error handled by error handler, severity: {Severity}", errorContext.Severity);
+                        }
+                    }
+                    catch (Exception handlerEx)
+                    {
+                        _logger.Warning(handlerEx, "Error handler threw an exception");
+                    }
+                }
+
+                // Check if we should retry based on error severity
+                if (errorContext.Severity == SynchronizerErrorSeverity.Fatal ||
+                    errorContext.Severity == SynchronizerErrorSeverity.AuthRequired)
+                {
+                    _logger.Warning(ex, "Non-retryable error (severity: {Severity}), failing immediately", errorContext.Severity);
+                    throw;
+                }
+
+                if (errorContext.Severity == SynchronizerErrorSeverity.Recoverable)
+                {
+                    _logger.Debug(ex, "Recoverable error, not retrying but allowing continuation");
+                    throw;
+                }
+
+                // Transient error - check if we have retries left
+                if (attempt > policy.MaxRetries)
+                {
+                    _logger.Warning(ex, "All {MaxRetries} retries exhausted", policy.MaxRetries);
+                    throw;
+                }
+
+                // Calculate delay and wait
+                var delay = errorContext.RetryDelay ?? policy.GetDelay(attempt);
+                _logger.Debug("Retry attempt {Attempt}/{MaxRetries} after {Delay}ms delay for error: {ErrorMessage}",
+                    attempt, policy.MaxRetries, delay.TotalMilliseconds, ex.Message);
+
+                await Task.Delay(delay, cancellationToken).ConfigureAwait(false);
+            }
+        }
+
+        // Should not reach here, but just in case
+        throw lastException ?? new InvalidOperationException("Retry loop completed without result");
+    }
+
+    /// <inheritdoc/>
+    public async Task ExecuteWithRetryAsync(
+        Func<CancellationToken, Task> operation,
+        RetryPolicy policy,
+        Func<Exception, SynchronizerErrorContext> errorContextFactory,
+        ISynchronizerErrorHandlerFactory errorHandler = null,
+        CancellationToken cancellationToken = default)
+    {
+        await ExecuteWithRetryAsync(
+            async ct =>
+            {
+                await operation(ct).ConfigureAwait(false);
+                return true; // Dummy return value
+            },
+            policy,
+            errorContextFactory,
+            errorHandler,
+            cancellationToken).ConfigureAwait(false);
+    }
+
+    /// <inheritdoc/>
+    public Task<T> ExecuteWithRetryAsync<T>(
+        Func<CancellationToken, Task<T>> operation,
+        Func<Exception, SynchronizerErrorContext> errorContextFactory,
+        CancellationToken cancellationToken = default)
+    {
+        return ExecuteWithRetryAsync(
+            operation,
+            RetryPolicy.Default,
+            errorContextFactory,
+            null,
+            cancellationToken);
+    }
+}

Wino.Core/Services/SynchronizerErrorHandlingFactory.cs

@@ -2,7 +2,7 @@ using System.Collections.Generic;
 using System.Threading.Tasks;
 using Serilog;
 using Wino.Core.Domain.Interfaces;
-using Wino.Core.Domain.Models.Errors;
+using Wino.Core.Domain.Models.Synchronization;
 
 namespace Wino.Core.Services;
 

Wino.Core/Services/SynchronizerFactory.cs

@@ -4,6 +4,7 @@ using System.Threading.Tasks;
 using Wino.Core.Domain.Entities.Shared;
 using Wino.Core.Domain.Interfaces;
 using Wino.Core.Integration.Processors;
+using Wino.Core.Synchronizers.ImapSync;
 using Wino.Core.Synchronizers.Mail;
 
 namespace Wino.Core.Services;
@@ -17,10 +18,12 @@ public class SynchronizerFactory : ISynchronizerFactory
     private readonly IApplicationConfiguration _applicationConfiguration;
     private readonly IOutlookSynchronizerErrorHandlerFactory _outlookSynchronizerErrorHandlerFactory;
     private readonly IGmailSynchronizerErrorHandlerFactory _gmailSynchronizerErrorHandlerFactory;
+    private readonly IImapSynchronizerErrorHandlerFactory _imapSynchronizerErrorHandlerFactory;
     private readonly IOutlookChangeProcessor _outlookChangeProcessor;
     private readonly IGmailChangeProcessor _gmailChangeProcessor;
     private readonly IImapChangeProcessor _imapChangeProcessor;
     private readonly IAuthenticationProvider _authenticationProvider;
+    private readonly UnifiedImapSynchronizer _unifiedImapSynchronizer;
 
     private readonly List<IWinoSynchronizerBase> synchronizerCache = new();
 
@@ -32,7 +35,9 @@ public class SynchronizerFactory : ISynchronizerFactory
                                IImapSynchronizationStrategyProvider imapSynchronizationStrategyProvider,
                                IApplicationConfiguration applicationConfiguration,
                                IOutlookSynchronizerErrorHandlerFactory outlookSynchronizerErrorHandlerFactory,
-                               IGmailSynchronizerErrorHandlerFactory gmailSynchronizerErrorHandlerFactory)
+                               IGmailSynchronizerErrorHandlerFactory gmailSynchronizerErrorHandlerFactory,
+                               IImapSynchronizerErrorHandlerFactory imapSynchronizerErrorHandlerFactory,
+                               UnifiedImapSynchronizer unifiedImapSynchronizer)
     {
         _outlookChangeProcessor = outlookChangeProcessor;
         _gmailChangeProcessor = gmailChangeProcessor;
@@ -43,6 +48,8 @@ public class SynchronizerFactory : ISynchronizerFactory
         _applicationConfiguration = applicationConfiguration;
         _outlookSynchronizerErrorHandlerFactory = outlookSynchronizerErrorHandlerFactory;
         _gmailSynchronizerErrorHandlerFactory = gmailSynchronizerErrorHandlerFactory;
+        _imapSynchronizerErrorHandlerFactory = imapSynchronizerErrorHandlerFactory;
+        _unifiedImapSynchronizer = unifiedImapSynchronizer;
     }
 
     public async Task<IWinoSynchronizerBase> GetAccountSynchronizerAsync(Guid accountId)
@@ -78,7 +85,7 @@ public class SynchronizerFactory : ISynchronizerFactory
                 var gmailAuthenticator = _authenticationProvider.GetAuthenticator(Domain.Enums.MailProviderType.Gmail) as IGmailAuthenticator;
                 return new GmailSynchronizer(mailAccount, gmailAuthenticator, _gmailChangeProcessor, _gmailSynchronizerErrorHandlerFactory);
             case Domain.Enums.MailProviderType.IMAP4:
-                return new ImapSynchronizer(mailAccount, _imapChangeProcessor, _imapSynchronizationStrategyProvider, _applicationConfiguration);
+                return new ImapSynchronizer(mailAccount, _imapChangeProcessor, _imapSynchronizationStrategyProvider, _applicationConfiguration, _unifiedImapSynchronizer, _imapSynchronizerErrorHandlerFactory);
             default:
                 break;
         }

Wino.Core/Synchronizers/Errors/Gmail/GmailHistoryExpiredHandler.cs

@@ -0,0 +1,78 @@
+using System;
+using System.Threading.Tasks;
+using Google;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+using Wino.Core.Integration.Processors;
+
+namespace Wino.Core.Synchronizers.Errors.Gmail;
+
+/// <summary>
+/// Handles Gmail history ID expiration errors.
+/// When history is no longer available, resets the account's history ID to force a full resync.
+/// </summary>
+public class GmailHistoryExpiredHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<GmailHistoryExpiredHandler>();
+    private readonly IGmailChangeProcessor _gmailChangeProcessor;
+
+    public GmailHistoryExpiredHandler(IGmailChangeProcessor gmailChangeProcessor)
+    {
+        _gmailChangeProcessor = gmailChangeProcessor;
+    }
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        // Gmail returns 404 when history ID is no longer valid
+        if (error.ErrorCode == 404)
+        {
+            var message = error.ErrorMessage?.ToLowerInvariant() ?? string.Empty;
+            return message.Contains("history") || message.Contains("notfound");
+        }
+
+        if (error.Exception is GoogleApiException googleEx)
+        {
+            if (googleEx.HttpStatusCode == System.Net.HttpStatusCode.NotFound)
+            {
+                var errorMessage = googleEx.Message?.ToLowerInvariant() ?? string.Empty;
+                return errorMessage.Contains("history") ||
+                       errorMessage.Contains("not found") ||
+                       errorMessage.Contains("starthistoryid");
+            }
+        }
+
+        return false;
+    }
+
+    public async Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        _logger.Warning(error.Exception,
+            "Gmail history ID expired for account {AccountName} ({AccountId}). Resetting to force full sync.",
+            error.Account?.Name, error.Account?.Id);
+
+        error.Severity = SynchronizerErrorSeverity.Recoverable;
+        error.Category = SynchronizerErrorCategory.ResourceNotFound;
+
+        // Reset the account's synchronization identifier (history ID)
+        if (error.Account != null)
+        {
+            try
+            {
+                await _gmailChangeProcessor.UpdateAccountDeltaSynchronizationIdentifierAsync(
+                    error.Account.Id, string.Empty).ConfigureAwait(false);
+
+                _logger.Information("Successfully reset Gmail history ID for account {AccountName}. Next sync will be full sync.",
+                    error.Account.Name);
+            }
+            catch (Exception ex)
+            {
+                _logger.Error(ex, "Failed to reset Gmail history ID for account {AccountName}",
+                    error.Account.Name);
+            }
+        }
+
+        return true;
+    }
+}

Wino.Core/Synchronizers/Errors/Gmail/GmailQuotaExceededHandler.cs

@@ -0,0 +1,57 @@
+using System;
+using System.Linq;
+using System.Threading.Tasks;
+using Google;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Synchronizers.Errors.Gmail;
+
+/// <summary>
+/// Handles Gmail API quota exceeded errors (HTTP 403 with quota error).
+/// This is a more severe rate limit that indicates daily quota exhaustion.
+/// </summary>
+public class GmailQuotaExceededHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<GmailQuotaExceededHandler>();
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        if (error.Exception is GoogleApiException googleEx)
+        {
+            // Quota exceeded usually returns 403
+            if (googleEx.HttpStatusCode == System.Net.HttpStatusCode.Forbidden)
+            {
+                var errorMessage = googleEx.Message?.ToLowerInvariant() ?? string.Empty;
+                var errorReason = googleEx.Error?.Errors?.FirstOrDefault()?.Reason?.ToLowerInvariant() ?? string.Empty;
+
+                return errorMessage.Contains("quota") ||
+                       errorMessage.Contains("limit exceeded") ||
+                       errorReason.Contains("quota") ||
+                       errorReason.Contains("ratelimitexceeded") ||
+                       errorReason.Contains("userlimitexceeded");
+            }
+        }
+
+        return false;
+    }
+
+    public Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        _logger.Warning(error.Exception,
+            "Gmail API quota exceeded for account {AccountName} ({AccountId}). Sync will be paused.",
+            error.Account?.Name, error.Account?.Id);
+
+        // Quota exceeded is more severe - treat as fatal to prevent repeated failures
+        // The user will be notified and sync will resume after quota resets
+        error.Severity = SynchronizerErrorSeverity.Fatal;
+        error.Category = SynchronizerErrorCategory.RateLimit;
+
+        // Suggest a very long delay - quotas typically reset daily
+        error.RetryDelay = TimeSpan.FromHours(1);
+
+        return Task.FromResult(true);
+    }
+}

Wino.Core/Synchronizers/Errors/Gmail/GmailRateLimitHandler.cs

@@ -0,0 +1,47 @@
+using System;
+using System.Threading.Tasks;
+using Google;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Synchronizers.Errors.Gmail;
+
+/// <summary>
+/// Handles Gmail API rate limiting errors (HTTP 429 Too Many Requests).
+/// Marks the error as transient with appropriate backoff delay.
+/// </summary>
+public class GmailRateLimitHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<GmailRateLimitHandler>();
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        if (error.ErrorCode == 429)
+            return true;
+
+        if (error.Exception is GoogleApiException googleEx)
+        {
+            return googleEx.HttpStatusCode == System.Net.HttpStatusCode.TooManyRequests ||
+                   (googleEx.Error?.Code == 429);
+        }
+
+        return false;
+    }
+
+    public Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        _logger.Warning(error.Exception,
+            "Gmail API rate limit hit for account {AccountName} ({AccountId}). Operation: {Operation}. Will retry with backoff.",
+            error.Account?.Name, error.Account?.Id, error.OperationType ?? "N/A");
+
+        error.Severity = SynchronizerErrorSeverity.Transient;
+        error.Category = SynchronizerErrorCategory.RateLimit;
+
+        // Gmail rate limits are usually per-user, suggest a longer delay
+        error.RetryDelay = TimeSpan.FromSeconds(10);
+
+        return Task.FromResult(true);
+    }
+}

Wino.Core/Synchronizers/Errors/Imap/ImapAuthenticationFailedHandler.cs

@@ -0,0 +1,40 @@
+using System.Threading.Tasks;
+using MailKit.Security;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Synchronizers.Errors.Imap;
+
+/// <summary>
+/// Handles IMAP authentication failures (AuthenticationException, SaslException).
+/// Marks the error as requiring re-authentication.
+/// </summary>
+public class ImapAuthenticationFailedHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<ImapAuthenticationFailedHandler>();
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        return error.Exception is AuthenticationException ||
+               error.Exception is SaslException ||
+               (error.ErrorMessage?.Contains("authentication", System.StringComparison.OrdinalIgnoreCase) ?? false);
+    }
+
+    public Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        _logger.Warning(error.Exception,
+            "IMAP authentication failed for account {AccountName} ({AccountId}). User needs to re-authenticate.",
+            error.Account?.Name, error.Account?.Id);
+
+        // Mark as requiring authentication - this will stop sync and notify user
+        error.Severity = SynchronizerErrorSeverity.AuthRequired;
+        error.Category = SynchronizerErrorCategory.Authentication;
+
+        // No point in retrying auth failures - credentials need to be updated
+        error.RetryDelay = null;
+
+        return Task.FromResult(true);
+    }
+}

Wino.Core/Synchronizers/Errors/Imap/ImapConnectionLostHandler.cs

@@ -0,0 +1,45 @@
+using System;
+using System.IO;
+using System.Net.Sockets;
+using System.Threading.Tasks;
+using MailKit;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Synchronizers.Errors.Imap;
+
+/// <summary>
+/// Handles IMAP connection loss errors (IOException, SocketException, ServiceNotConnectedException).
+/// Marks the error as transient for retry with backoff.
+/// </summary>
+public class ImapConnectionLostHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<ImapConnectionLostHandler>();
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        return error.Exception is IOException ||
+               error.Exception is SocketException ||
+               error.Exception is ServiceNotConnectedException ||
+               error.Exception?.InnerException is IOException ||
+               error.Exception?.InnerException is SocketException;
+    }
+
+    public Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        _logger.Warning(error.Exception,
+            "IMAP connection lost for account {AccountName} ({AccountId}). Folder: {FolderName}. Operation: {Operation}. Will retry.",
+            error.Account?.Name, error.Account?.Id, error.FolderName ?? "N/A", error.OperationType ?? "N/A");
+
+        // Mark as transient - the RetryExecutor will handle the retry logic
+        error.Severity = SynchronizerErrorSeverity.Transient;
+        error.Category = SynchronizerErrorCategory.Network;
+
+        // Suggest a reasonable retry delay for connection issues
+        error.RetryDelay = TimeSpan.FromSeconds(2);
+
+        return Task.FromResult(true);
+    }
+}

Wino.Core/Synchronizers/Errors/Imap/ImapFolderNotFoundHandler.cs

@@ -0,0 +1,67 @@
+using System.Threading.Tasks;
+using MailKit;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+using Wino.Core.Integration.Processors;
+
+namespace Wino.Core.Synchronizers.Errors.Imap;
+
+/// <summary>
+/// Handles IMAP folder not found errors (FolderNotFoundException).
+/// Deletes the folder locally and allows sync to continue with other folders.
+/// </summary>
+public class ImapFolderNotFoundHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<ImapFolderNotFoundHandler>();
+    private readonly IImapChangeProcessor _imapChangeProcessor;
+
+    public ImapFolderNotFoundHandler(IImapChangeProcessor imapChangeProcessor)
+    {
+        _imapChangeProcessor = imapChangeProcessor;
+    }
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        return error.Exception is FolderNotFoundException ||
+               error.ErrorCode == 404 ||
+               (error.ErrorMessage?.Contains("folder not found", System.StringComparison.OrdinalIgnoreCase) ?? false) ||
+               (error.ErrorMessage?.Contains("mailbox not found", System.StringComparison.OrdinalIgnoreCase) ?? false);
+    }
+
+    public async Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        _logger.Warning(error.Exception,
+            "IMAP folder not found for account {AccountName} ({AccountId}). Folder: {FolderName} ({FolderId}). Removing locally.",
+            error.Account?.Name, error.Account?.Id, error.FolderName, error.FolderId);
+
+        // Mark as recoverable - sync can continue with other folders
+        error.Severity = SynchronizerErrorSeverity.Recoverable;
+        error.Category = SynchronizerErrorCategory.ResourceNotFound;
+
+        // Try to delete the folder locally if we have the folder ID
+        if (error.FolderId.HasValue && error.Account != null)
+        {
+            try
+            {
+                // Get the folder's remote ID from the exception if available
+                var remoteId = error.Exception is FolderNotFoundException fnf ? fnf.FolderName : null;
+
+                if (!string.IsNullOrEmpty(remoteId))
+                {
+                    await _imapChangeProcessor.DeleteFolderAsync(error.Account.Id, remoteId).ConfigureAwait(false);
+                    _logger.Information("Successfully deleted local folder {FolderName} after server deletion.",
+                        error.FolderName);
+                }
+            }
+            catch (System.Exception ex)
+            {
+                _logger.Warning(ex, "Failed to delete local folder {FolderName} ({FolderId})",
+                    error.FolderName, error.FolderId);
+            }
+        }
+
+        return true;
+    }
+}

Wino.Core/Synchronizers/Errors/Imap/ImapProtocolErrorHandler.cs

@@ -0,0 +1,100 @@
+using System;
+using System.Threading.Tasks;
+using MailKit.Net.Imap;
+using Serilog;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Synchronization;
+
+namespace Wino.Core.Synchronizers.Errors.Imap;
+
+/// <summary>
+/// Handles generic IMAP protocol errors (ImapProtocolException, ImapCommandException).
+/// This is the catch-all handler for IMAP errors not handled by more specific handlers.
+/// </summary>
+public class ImapProtocolErrorHandler : ISynchronizerErrorHandler
+{
+    private readonly ILogger _logger = Log.ForContext<ImapProtocolErrorHandler>();
+
+    public bool CanHandle(SynchronizerErrorContext error)
+    {
+        // This is a catch-all for IMAP-related exceptions
+        return error.Exception is ImapProtocolException ||
+               error.Exception is ImapCommandException;
+    }
+
+    public Task<bool> HandleAsync(SynchronizerErrorContext error)
+    {
+        var severity = ClassifyProtocolError(error);
+        var category = SynchronizerErrorCategory.ProtocolError;
+
+        _logger.Warning(error.Exception,
+            "IMAP protocol error for account {AccountName} ({AccountId}). Folder: {FolderName}. Operation: {Operation}. Severity: {Severity}",
+            error.Account?.Name, error.Account?.Id, error.FolderName ?? "N/A", error.OperationType ?? "N/A", severity);
+
+        error.Severity = severity;
+        error.Category = category;
+
+        // For transient protocol errors, suggest a retry delay
+        if (severity == SynchronizerErrorSeverity.Transient)
+        {
+            error.RetryDelay = TimeSpan.FromSeconds(5);
+        }
+
+        return Task.FromResult(true);
+    }
+
+    /// <summary>
+    /// Classifies the protocol error to determine if it's transient, recoverable, or fatal.
+    /// </summary>
+    private static SynchronizerErrorSeverity ClassifyProtocolError(SynchronizerErrorContext error)
+    {
+        var message = error.ErrorMessage?.ToLowerInvariant() ?? string.Empty;
+        var exMessage = error.Exception?.Message?.ToLowerInvariant() ?? string.Empty;
+
+        // Check for rate limiting / throttling
+        if (message.Contains("too many") || message.Contains("rate limit") ||
+            message.Contains("throttl") || exMessage.Contains("too many"))
+        {
+            return SynchronizerErrorSeverity.Transient;
+        }
+
+        // Check for temporary server issues
+        if (message.Contains("try again") || message.Contains("temporary") ||
+            message.Contains("busy") || exMessage.Contains("try again"))
+        {
+            return SynchronizerErrorSeverity.Transient;
+        }
+
+        // Check for command-specific errors that are usually transient
+        if (error.Exception is ImapCommandException cmdEx)
+        {
+            // NO response usually means the operation failed but can be retried
+            if (cmdEx.Response == ImapCommandResponse.No)
+            {
+                // Unless it's a permanent failure indication
+                if (message.Contains("permanent") || message.Contains("invalid"))
+                {
+                    return SynchronizerErrorSeverity.Recoverable;
+                }
+                return SynchronizerErrorSeverity.Transient;
+            }
+
+            // BAD response usually indicates a protocol violation - don't retry
+            if (cmdEx.Response == ImapCommandResponse.Bad)
+            {
+                return SynchronizerErrorSeverity.Recoverable;
+            }
+        }
+
+        // Protocol exceptions that indicate connection issues
+        if (error.Exception is ImapProtocolException)
+        {
+            // Most protocol exceptions are connection-related and transient
+            return SynchronizerErrorSeverity.Transient;
+        }
+
+        // Default to recoverable for unknown protocol errors
+        return SynchronizerErrorSeverity.Recoverable;
+    }
+}

Wino.Core/Synchronizers/Errors/Outlook/DeltaTokenExpiredHandler.cs

@@ -3,7 +3,7 @@ using Microsoft.Graph.Models.ODataErrors;
 using Microsoft.Kiota.Abstractions;
 using Serilog;
 using Wino.Core.Domain.Interfaces;
-using Wino.Core.Domain.Models.Errors;
+using Wino.Core.Domain.Models.Synchronization;
 using Wino.Core.Integration.Processors;
 
 namespace Wino.Core.Synchronizers.Errors.Outlook;

Wino.Core/Synchronizers/Errors/Outlook/ObjectCannotBeDeletedHandler.cs

@@ -1,8 +1,8 @@
 using System.Threading.Tasks;
 using Microsoft.Kiota.Abstractions;
 using Wino.Core.Domain.Interfaces;
-using Wino.Core.Domain.Models.Errors;
 using Wino.Core.Domain.Models.Requests;
+using Wino.Core.Domain.Models.Synchronization;
 using Wino.Core.Requests.Bundles;
 
 namespace Wino.Core.Synchronizers.Errors.Outlook;

Wino.Core/Synchronizers/GmailSynchronizer.cs

@@ -8,7 +8,6 @@ using System.Threading.Tasks;
 using System.Web;
 using CommunityToolkit.Mvvm.Messaging;
 using Google;
-using Google.Apis.Calendar.v3;
 using Google.Apis.Calendar.v3.Data;
 using Google.Apis.Gmail.v1;
 using Google.Apis.Gmail.v1.Data;
@@ -28,7 +27,6 @@ using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Exceptions;
 using Wino.Core.Domain.Interfaces;
 using Wino.Core.Domain.Models.Accounts;
-using Wino.Core.Domain.Models.Errors;
 using Wino.Core.Domain.Models.Folders;
 using Wino.Core.Domain.Models.MailItem;
 using Wino.Core.Domain.Models.Synchronization;
@@ -51,19 +49,22 @@ namespace Wino.Core.Synchronizers.Mail;
 public partial class GmailSynchronizerJsonContext : JsonSerializerContext;
 
 /// <summary>
-/// Gmail synchronizer implementation with per-folder history ID synchronization.
-/// 
+/// Gmail synchronizer implementation using Gmail History API for efficient incremental sync.
+///
 /// SYNCHRONIZATION STRATEGY:
-/// - Uses Gmail History API for both initial and incremental sync
-/// - Initial sync: Downloads top 1500 messages per folder with metadata only
-/// - Incremental sync: Uses history ID to get only changes since last sync
-/// - Messages are downloaded with metadata only (no MIME content during sync)
-/// - MIME files are downloaded on-demand when user explicitly reads a message
-/// 
+/// - Initial sync: Downloads up to 1500 messages PER FOLDER with metadata only.
+///   Uses a global HashSet to track downloaded message IDs, avoiding duplicate downloads
+///   when messages have multiple labels. Each folder gets its full quota of messages.
+/// - Incremental sync: Uses ONLY History API to get changes since last sync.
+///   No per-folder downloads during incremental sync - this is the proper Gmail sync approach.
+/// - Messages are downloaded with metadata only during initial sync (no MIME content)
+/// - New messages during incremental sync are downloaded with full MIME content
+/// - MIME files for initial sync messages are downloaded on-demand when user reads a message
+///
 /// Key implementation details:
-/// - SynchronizeFolderAsync: Main entry point for per-folder synchronization
-/// - DownloadMessagesForFolderAsync: Downloads top 1500 messages for initial sync
-/// - SynchronizeDeltaAsync: Processes incremental changes using history ID
+/// - PerformInitialSyncAsync: Downloads messages per-folder with global deduplication
+/// - SynchronizeDeltaAsync: Processes incremental changes using History API with pagination
+/// - Handles 404/410 errors (history expired) by triggering full resync
 /// - CreateMinimalMailCopyAsync: Extracts MailCopy fields from Gmail Metadata format
 /// - DownloadMissingMimeMessageAsync: Downloads raw MIME only when explicitly requested
 /// </summary>
@@ -153,15 +154,16 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
     {
         _logger.Information("Internal mail synchronization started for {Name}", Account.Name);
 
-        // Make sure that virtual archive folder exists before all.
-        if (!archiveFolderId.HasValue)
-            await InitializeArchiveFolderAsync().ConfigureAwait(false);
+        var downloadedMessageIds = new List<string>();
+        var folderResults = new List<FolderSyncResult>();
 
-        // Gmail must always synchronize folders before because it doesn't have a per-folder sync.
-        bool shouldSynchronizeFolders = true;
-
-        if (shouldSynchronizeFolders)
+        try
         {
+            // Make sure that virtual archive folder exists before all.
+            if (!archiveFolderId.HasValue)
+                await InitializeArchiveFolderAsync().ConfigureAwait(false);
+
+            // Gmail must always synchronize folders before because it doesn't have a per-folder sync.
             _logger.Information("Synchronizing folders for {Name}", Account.Name);
             UpdateSyncProgress(0, 0, "Synchronizing folders...");
 
@@ -173,202 +175,291 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             {
                 throw new GmailServiceDisabledException();
             }
-            catch (Exception)
-            {
-                throw;
-            }
 
             _logger.Information("Synchronizing folders for {Name} is completed", Account.Name);
             UpdateSyncProgress(0, 0, "Folders synchronized");
+
+            // Stop synchronization at this point if type is only folder metadata sync.
+            if (options.Type == MailSynchronizationType.FoldersOnly) return MailSynchronizationResult.Empty;
+
+            cancellationToken.ThrowIfCancellationRequested();
+
+            bool isInitialSync = string.IsNullOrEmpty(Account.SynchronizationDeltaIdentifier);
+
+            _logger.Debug("Is initial synchronization: {IsInitialSync}", isInitialSync);
+
+            if (isInitialSync)
+            {
+                // INITIAL SYNC: Download all messages globally (not per-folder) to avoid duplicates.
+                // Gmail messages can have multiple labels, so per-folder download would fetch same message multiple times.
+                downloadedMessageIds = await PerformInitialSyncAsync(cancellationToken).ConfigureAwait(false);
+
+                // Set the history ID to the latest value after initial sync
+                UpdateSyncProgress(0, 0, "Finalizing synchronization...");
+                var profile = await _gmailService.Users.GetProfile("me").ExecuteAsync(cancellationToken);
+                if (profile.HistoryId.HasValue)
+                {
+                    await UpdateAccountSyncIdentifierAsync(profile.HistoryId.Value).ConfigureAwait(false);
+                    _logger.Information("Initial sync completed. Set history ID to {HistoryId}", profile.HistoryId.Value);
+                }
+
+                // Create successful folder results for all folders
+                var allFolders = await _gmailChangeProcessor.GetSynchronizationFoldersAsync(options).ConfigureAwait(false);
+                foreach (var folder in allFolders.Where(f => f.RemoteFolderId != ServiceConstants.ARCHIVE_LABEL_ID))
+                {
+                    folderResults.Add(FolderSyncResult.Successful(folder.Id, folder.FolderName, 0));
+                }
+            }
+            else
+            {
+                // INCREMENTAL SYNC: Use ONLY History API - no per-folder downloads.
+                // This is the proper Gmail sync strategy as recommended by Google.
+                UpdateSyncProgress(0, 0, "Synchronizing changes...");
+                var deltaResult = await SynchronizeDeltaAsync(options, cancellationToken).ConfigureAwait(false);
+                downloadedMessageIds.AddRange(deltaResult.DownloadedMessageIds);
+
+                // If history sync was reset due to expired history ID, we need to do initial sync
+                if (deltaResult.RequiresFullResync)
+                {
+                    _logger.Warning("History ID expired. Performing full resync for {Name}", Account.Name);
+                    downloadedMessageIds = await PerformInitialSyncAsync(cancellationToken).ConfigureAwait(false);
+
+                    // Update history ID after full resync
+                    var profile = await _gmailService.Users.GetProfile("me").ExecuteAsync(cancellationToken);
+                    if (profile.HistoryId.HasValue)
+                    {
+                        await UpdateAccountSyncIdentifierAsync(profile.HistoryId.Value).ConfigureAwait(false);
+                        _logger.Information("Full resync completed. Set history ID to {HistoryId}", profile.HistoryId.Value);
+                    }
+                }
+
+                UpdateSyncProgress(0, 0, "Changes synchronized");
+
+                // Create folder results for incremental sync
+                var allFolders = await _gmailChangeProcessor.GetSynchronizationFoldersAsync(options).ConfigureAwait(false);
+                foreach (var folder in allFolders.Where(f => f.RemoteFolderId != ServiceConstants.ARCHIVE_LABEL_ID))
+                {
+                    folderResults.Add(FolderSyncResult.Successful(folder.Id, folder.FolderName, 0));
+                }
+            }
         }
-
-        // There is no specific folder synchronization in Gmail.
-        // Therefore we need to stop the synchronization at this point
-        // if type is only folder metadata sync.
-
-        if (options.Type == MailSynchronizationType.FoldersOnly) return MailSynchronizationResult.Empty;
-
-        cancellationToken.ThrowIfCancellationRequested();
-
-        bool isInitialSync = string.IsNullOrEmpty(Account.SynchronizationDeltaIdentifier);
-
-        _logger.Debug("Is initial synchronization: {IsInitialSync}", isInitialSync);
-
-        var downloadedMessageIds = new List<string>();
-
-        // Get all folders to synchronize
-        var synchronizationFolders = await _gmailChangeProcessor.GetSynchronizationFoldersAsync(options).ConfigureAwait(false);
-
-        _logger.Information("Synchronizing {Count} folders for {Name}", synchronizationFolders.Count, Account.Name);
-
-        var totalFolders = synchronizationFolders.Count;
-
-        for (int i = 0; i < totalFolders; i++)
+        catch (OperationCanceledException)
         {
-            var folder = synchronizationFolders[i];
-
-            // Update progress based on folder completion
-            UpdateSyncProgress(totalFolders, totalFolders - (i + 1), $"Syncing {folder.FolderName}...");
-
-            var folderDownloadedMessageIds = await SynchronizeFolderAsync(folder, cancellationToken).ConfigureAwait(false);
-            downloadedMessageIds.AddRange(folderDownloadedMessageIds);
+            _logger.Information("Synchronization was canceled for {Name}", Account.Name);
+            return MailSynchronizationResult.Canceled;
         }
-
-        // Process incremental changes using history API if we have a history ID
-        if (!string.IsNullOrEmpty(Account.SynchronizationDeltaIdentifier))
+        catch (Exception ex)
         {
-            UpdateSyncProgress(0, 0, "Synchronizing changes...");
-            await SynchronizeDeltaAsync(options, cancellationToken).ConfigureAwait(false);
-            UpdateSyncProgress(0, 0, "Changes synchronized");
+            _logger.Error(ex, "Synchronization failed for {Name}", Account.Name);
+            return MailSynchronizationResult.Failed(ex);
         }
 
         // Get all unread new downloaded items for notifications
         var unreadNewItems = await _gmailChangeProcessor.GetDownloadedUnreadMailsAsync(Account.Id, downloadedMessageIds).ConfigureAwait(false);
 
-        return MailSynchronizationResult.Completed(unreadNewItems);
+        return MailSynchronizationResult.CompletedWithFolderResults(unreadNewItems, folderResults);
     }
 
     /// <summary>
-    /// Synchronizes a single folder by downloading top 1500 messages with metadata only.
+    /// Result of delta synchronization using History API.
     /// </summary>
-    private async Task<List<string>> SynchronizeFolderAsync(MailItemFolder folder, CancellationToken cancellationToken)
-    {
-        var downloadedMessageIds = new List<string>();
-
-        cancellationToken.ThrowIfCancellationRequested();
-
-        _logger.Debug("Synchronizing folder {FolderName} (label: {LabelId})", folder.FolderName, folder.RemoteFolderId);
-
-        try
-        {
-            // Download top 1500 messages for this folder
-            await DownloadMessagesForFolderAsync(folder, downloadedMessageIds, cancellationToken).ConfigureAwait(false);
-
-            if (downloadedMessageIds.Any())
-            {
-                _logger.Information("Downloaded {Count} messages for folder {FolderName}", downloadedMessageIds.Count, folder.FolderName);
-            }
-        }
-        catch (Exception ex)
-        {
-            _logger.Error(ex, "Error synchronizing folder {FolderName}", folder.FolderName);
-            throw;
-        }
-
-        return downloadedMessageIds;
-    }
+    private record DeltaSyncResult(List<string> DownloadedMessageIds, bool RequiresFullResync);
 
     /// <summary>
-    /// Downloads top 1500 messages for a folder using Gmail API with metadata only.
+    /// Performs initial synchronization by downloading messages per-folder.
+    /// Each folder gets up to 1500 messages, but we track already downloaded message IDs globally
+    /// to avoid downloading the same message multiple times (Gmail messages can have multiple labels).
     /// </summary>
-    private async Task DownloadMessagesForFolderAsync(MailItemFolder folder, List<string> downloadedMessageIds, CancellationToken cancellationToken)
+    private async Task<List<string>> PerformInitialSyncAsync(CancellationToken cancellationToken)
     {
-        _logger.Debug("Downloading messages for folder {FolderName}", folder.FolderName);
+        // Track all downloaded message IDs globally to avoid duplicate downloads
+        var downloadedMessageIds = new HashSet<string>();
+
+        _logger.Information("Performing initial sync for {Name} - downloading messages per folder", Account.Name);
 
         try
         {
-            var totalDownloaded = 0;
-            string pageToken = null;
+            // Get all folders to sync (exclude virtual ARCHIVE folder)
+            var folders = await _gmailChangeProcessor.GetLocalFoldersAsync(Account.Id).ConfigureAwait(false);
+            var syncableFolders = folders
+                .Where(f => f.IsSynchronizationEnabled && f.RemoteFolderId != ServiceConstants.ARCHIVE_LABEL_ID)
+                .ToList();
 
-            // Gmail API returns messages newest first by default
-            // We'll download up to 1500 messages per folder
-            var remainingToDownload = (int)InitialMessageDownloadCountPerFolder;
+            var totalFolders = syncableFolders.Count;
+            var totalMessagesDownloaded = 0;
 
-            do
+            for (int i = 0; i < totalFolders; i++)
             {
+                var folder = syncableFolders[i];
                 cancellationToken.ThrowIfCancellationRequested();
 
-                var request = _gmailService.Users.Messages.List("me");
-                request.LabelIds = new Google.Apis.Util.Repeatable<string>(new[] { folder.RemoteFolderId });
-                request.MaxResults = Math.Min(remainingToDownload, 500); // API max is 500
-                request.PageToken = pageToken;
+                UpdateSyncProgress(totalFolders, totalFolders - (i + 1), $"Syncing {folder.FolderName}...");
 
-                var response = await request.ExecuteAsync(cancellationToken);
+                _logger.Debug("Downloading messages for folder {FolderName} (label: {LabelId})", folder.FolderName, folder.RemoteFolderId);
 
-                if (response.Messages != null && response.Messages.Count > 0)
+                var folderDownloaded = 0;
+                string pageToken = null;
+                var remainingToDownload = (int)InitialMessageDownloadCountPerFolder;
+
+                do
                 {
-                    var messageIds = response.Messages.Select(m => m.Id).ToList();
+                    cancellationToken.ThrowIfCancellationRequested();
 
-                    // Download metadata in batches
-                    await DownloadMessagesInBatchAsync(messageIds, downloadRawMime: false, cancellationToken).ConfigureAwait(false);
+                    var request = _gmailService.Users.Messages.List("me");
+                    request.LabelIds = new Google.Apis.Util.Repeatable<string>(new[] { folder.RemoteFolderId });
+                    request.MaxResults = Math.Min(remainingToDownload, 500); // API max is 500
+                    request.PageToken = pageToken;
 
-                    downloadedMessageIds.AddRange(messageIds);
-                    totalDownloaded += messageIds.Count;
-                    remainingToDownload -= messageIds.Count;
+                    var response = await request.ExecuteAsync(cancellationToken);
 
-                    _logger.Debug("Downloaded {Count} messages for folder {FolderName} (total: {Total})", messageIds.Count, folder.FolderName, totalDownloaded);
+                    if (response.Messages != null && response.Messages.Count > 0)
+                    {
+                        // Filter out already downloaded messages to avoid duplicates
+                        var newMessageIds = response.Messages
+                            .Select(m => m.Id)
+                            .Where(id => !downloadedMessageIds.Contains(id))
+                            .ToList();
 
-                    // Update progress
-                    UpdateSyncProgress(0, 0, $"Downloaded {totalDownloaded} messages from {folder.FolderName}");
-                }
+                        if (newMessageIds.Count > 0)
+                        {
+                            // Download metadata in batches (no raw MIME during initial sync)
+                            await DownloadMessagesInBatchAsync(newMessageIds, downloadRawMime: false, cancellationToken).ConfigureAwait(false);
 
-                pageToken = response.NextPageToken;
+                            foreach (var id in newMessageIds)
+                            {
+                                downloadedMessageIds.Add(id);
+                            }
 
-                // Stop if we've downloaded enough messages or no more pages
-                if (remainingToDownload <= 0 || string.IsNullOrEmpty(pageToken))
-                    break;
+                            folderDownloaded += newMessageIds.Count;
+                            totalMessagesDownloaded += newMessageIds.Count;
+                        }
 
-            } while (!string.IsNullOrEmpty(pageToken));
+                        // Count all messages (including duplicates) toward the folder limit
+                        remainingToDownload -= response.Messages.Count;
 
-            // Store history ID for future incremental syncs
-            var profile = await _gmailService.Users.GetProfile("me").ExecuteAsync(cancellationToken);
-            Account.SynchronizationDeltaIdentifier = profile.HistoryId.ToString();
-            await _gmailChangeProcessor.UpdateAccountAsync(Account).ConfigureAwait(false);
+                        _logger.Debug("Folder {FolderName}: Downloaded {New} new messages ({Total} total in folder)",
+                            folder.FolderName, newMessageIds.Count, folderDownloaded);
+                    }
 
-            _logger.Information("Completed downloading {Count} messages for folder {FolderName}", totalDownloaded, folder.FolderName);
+                    pageToken = response.NextPageToken;
+
+                    // Stop if we've processed enough messages for this folder or no more pages
+                    if (remainingToDownload <= 0 || string.IsNullOrEmpty(pageToken))
+                        break;
+
+                } while (!string.IsNullOrEmpty(pageToken));
+
+                _logger.Information("Folder {FolderName}: Downloaded {Count} messages", folder.FolderName, folderDownloaded);
+                UpdateSyncProgress(0, 0, $"Downloaded {totalMessagesDownloaded} messages");
+            }
+
+            _logger.Information("Initial sync completed. Downloaded {Count} unique messages for {Name}", downloadedMessageIds.Count, Account.Name);
         }
         catch (GoogleApiException ex) when (ex.HttpStatusCode == System.Net.HttpStatusCode.TooManyRequests)
         {
-            _logger.Warning("Rate limit exceeded while downloading messages for folder {FolderName}. Retrying after delay.", folder.FolderName);
+            _logger.Warning("Rate limit exceeded during initial sync. Retrying after delay.");
             await Task.Delay(TimeSpan.FromSeconds(10), cancellationToken);
             throw;
         }
         catch (Exception ex)
         {
-            _logger.Error(ex, "Error downloading messages for folder {FolderName}", folder.FolderName);
+            _logger.Error(ex, "Error during initial sync for {Name}", Account.Name);
             throw;
         }
+
+        return downloadedMessageIds.ToList();
     }
 
-    private async Task SynchronizeDeltaAsync(MailSynchronizationOptions options, CancellationToken cancellationToken = default)
+    /// <summary>
+    /// Performs incremental synchronization using Gmail History API.
+    /// This is the recommended approach for Gmail sync after initial sync is complete.
+    /// Returns a result indicating downloaded messages and whether a full resync is needed.
+    /// </summary>
+    private async Task<DeltaSyncResult> SynchronizeDeltaAsync(MailSynchronizationOptions options, CancellationToken cancellationToken = default)
     {
+        var downloadedMessageIds = new List<string>();
+
         try
         {
-            var historyRequest = _gmailService.Users.History.List("me");
-            historyRequest.StartHistoryId = ulong.Parse(Account.SynchronizationDeltaIdentifier!);
+            string pageToken = null;
 
-            var historyResponse = await historyRequest.ExecuteAsync();
-
-            if (historyResponse.History != null)
+            do
             {
-                var addedMessageIds = new List<string>();
+                cancellationToken.ThrowIfCancellationRequested();
 
-                // Collect all added messages first
-                foreach (var historyRecord in historyResponse.History)
+                var historyRequest = _gmailService.Users.History.List("me");
+                historyRequest.StartHistoryId = ulong.Parse(Account.SynchronizationDeltaIdentifier!);
+
+                if (!string.IsNullOrEmpty(pageToken))
+                    historyRequest.PageToken = pageToken;
+
+                var historyResponse = await historyRequest.ExecuteAsync(cancellationToken);
+
+                if (historyResponse.History != null)
                 {
-                    if (historyRecord.MessagesAdded != null)
+                    var addedMessageIds = new List<string>();
+
+                    // Collect all added messages first
+                    foreach (var historyRecord in historyResponse.History)
                     {
-                        addedMessageIds.AddRange(historyRecord.MessagesAdded.Select(ma => ma.Message.Id));
+                        if (historyRecord.MessagesAdded != null)
+                        {
+                            addedMessageIds.AddRange(historyRecord.MessagesAdded.Select(ma => ma.Message.Id));
+                        }
                     }
-                }
 
-                // Process added messages in batches if any
-                // During delta sync, download with Raw format to get MIME content
-                if (addedMessageIds.Count != 0)
-                {
-                    await DownloadMessagesInBatchAsync(addedMessageIds, downloadRawMime: true, cancellationToken).ConfigureAwait(false);
-                }
+                    // Process added messages in batches if any
+                    // During delta sync, download with Raw format to get MIME content for new messages
+                    if (addedMessageIds.Count != 0)
+                    {
+                        // Deduplicate message IDs
+                        var uniqueAddedIds = addedMessageIds.Distinct().ToList();
+                        await DownloadMessagesInBatchAsync(uniqueAddedIds, downloadRawMime: true, cancellationToken).ConfigureAwait(false);
+                        downloadedMessageIds.AddRange(uniqueAddedIds);
+                    }
 
-                // Process other history changes
-                foreach (var historyRecord in historyResponse.History)
-                {
+                    // Process other history changes (label changes, deletions)
                     await ProcessHistoryChangesAsync(historyResponse).ConfigureAwait(false);
                 }
-            }
-        }
-        catch (Exception)
-        {
 
+                // CRITICAL: Update the history ID to the latest one after processing all changes
+                // History IDs are always incremental, so the response contains the latest history ID
+                if (historyResponse.HistoryId.HasValue)
+                {
+                    await UpdateAccountSyncIdentifierAsync(historyResponse.HistoryId.Value).ConfigureAwait(false);
+                    _logger.Debug("Updated history ID to {HistoryId} after delta sync", historyResponse.HistoryId.Value);
+                }
+
+                pageToken = historyResponse.NextPageToken;
+
+            } while (!string.IsNullOrEmpty(pageToken));
+
+            _logger.Information("Delta sync completed. Downloaded {Count} new messages for {Name}", downloadedMessageIds.Count, Account.Name);
+
+            return new DeltaSyncResult(downloadedMessageIds, RequiresFullResync: false);
+        }
+        catch (GoogleApiException ex) when (ex.HttpStatusCode == System.Net.HttpStatusCode.NotFound ||
+                                            (int)ex.HttpStatusCode == 410) // Gone - history expired
+        {
+            // History ID is no longer valid (expired or not found)
+            // This happens when:
+            // 1. The history ID is too old (Gmail keeps history for ~30 days)
+            // 2. The account was reset or history was cleared
+            // Reset the sync identifier and signal that a full resync is needed
+            _logger.Warning("History ID {HistoryId} expired or not found for {Name}. Full resync required. Error: {Error}",
+                Account.SynchronizationDeltaIdentifier, Account.Name, ex.Message);
+
+            // Clear the sync identifier to trigger initial sync
+            Account.SynchronizationDeltaIdentifier = await _gmailChangeProcessor
+                .UpdateAccountDeltaSynchronizationIdentifierAsync(Account.Id, null)
+                .ConfigureAwait(false);
+
+            return new DeltaSyncResult(downloadedMessageIds, RequiresFullResync: true);
+        }
+        catch (GoogleApiException ex) when (ex.HttpStatusCode == System.Net.HttpStatusCode.TooManyRequests)
+        {
+            _logger.Warning("Rate limit exceeded during delta sync for {Name}. Retrying after delay.", Account.Name);
+            await Task.Delay(TimeSpan.FromSeconds(10), cancellationToken);
             throw;
         }
     }
@@ -802,6 +893,13 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
 
         foreach (var labelId in addedLabel.LabelIds)
         {
+            // ARCHIVE is a virtual folder - handle it separately
+            if (labelId == ServiceConstants.ARCHIVE_LABEL_ID)
+            {
+                await HandleArchiveAssignmentAsync(messageId).ConfigureAwait(false);
+                continue;
+            }
+
             // When UNREAD label is added mark the message as un-read.
             if (labelId == ServiceConstants.UNREAD_LABEL_ID)
                 await _gmailChangeProcessor.ChangeMailReadStatusAsync(messageId, false).ConfigureAwait(false);
@@ -822,6 +920,13 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
 
         foreach (var labelId in removedLabel.LabelIds)
         {
+            // ARCHIVE is a virtual folder - handle it separately
+            if (labelId == ServiceConstants.ARCHIVE_LABEL_ID)
+            {
+                await HandleUnarchiveAssignmentAsync(messageId).ConfigureAwait(false);
+                continue;
+            }
+
             // When UNREAD label is removed mark the message as read.
             if (labelId == ServiceConstants.UNREAD_LABEL_ID)
                 await _gmailChangeProcessor.ChangeMailReadStatusAsync(messageId, true).ConfigureAwait(false);
@@ -1160,15 +1265,11 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
 
                     if (packages != null)
                     {
-                        // For Gmail, multiple packages can share the same message (different labels/folders)
-                        // They should all share the same FileId so MIME is stored only once
-                        Guid sharedFileId = Guid.NewGuid();
+                        // For Gmail, multiple packages share the same message (different labels/folders)
+                        // They already share the same FileId (set in CreateNewMailPackagesAsync) so MIME is stored only once
 
                         foreach (var package in packages)
                         {
-                            // Set the same FileId for all copies
-                            package.Copy.FileId = sharedFileId;
-
                             // Create the mail copy with the MIME (if downloaded)
                             var packageWithMime = downloadRawMime && mimeMessage != null
                                 ? new NewMailItemPackage(package.Copy, mimeMessage, package.AssignedRemoteFolderId)
@@ -1256,7 +1357,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             // Gmail calendar attachments are stored in Google Drive
             // RemoteAttachmentId contains either FileId or FileUrl
             // For simplicity, we'll try to download from the FileId/FileUrl
-            
+
             if (string.IsNullOrEmpty(attachment.RemoteAttachmentId))
             {
                 _logger.Error("RemoteAttachmentId is empty for attachment {AttachmentId}", attachment.Id);
@@ -1267,7 +1368,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             // The attachment.RemoteAttachmentId is either a FileId or FileUrl
             // Since we can't directly download from Calendar API, this would require Drive API access
             // For now, throw NotSupportedException as Gmail attachments require additional Drive API setup
-            
+
             _logger.Warning("Gmail calendar attachment download requires Google Drive API access. FileId/URL: {RemoteId}", attachment.RemoteAttachmentId);
             throw new NotSupportedException("Gmail calendar attachments are stored in Google Drive and require additional API configuration to download.");
         }
@@ -1615,7 +1716,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
 
         // Check Content-Type header for text/calendar
         var contentTypeHeader = headers.FirstOrDefault(h => h.Name.Equals("Content-Type", StringComparison.OrdinalIgnoreCase))?.Value;
-        
+
         if (!string.IsNullOrEmpty(contentTypeHeader))
         {
             // Check if it's a calendar message (text/calendar or multipart with calendar)
@@ -1623,11 +1724,11 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             {
                 // Check the METHOD parameter to determine invitation type
                 var methodMatch = System.Text.RegularExpressions.Regex.Match(contentTypeHeader, @"method=([^;\s]+)", System.Text.RegularExpressions.RegexOptions.IgnoreCase);
-                
+
                 if (methodMatch.Success)
                 {
                     var method = methodMatch.Groups[1].Value.Trim('"').ToUpperInvariant();
-                    
+
                     return method switch
                     {
                         "REQUEST" => MailItemType.CalendarInvitation,
@@ -1636,7 +1737,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
                         _ => MailItemType.Mail
                     };
                 }
-                
+
                 // If no method specified, assume it's an invitation
                 return MailItemType.CalendarInvitation;
             }
@@ -1683,11 +1784,11 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
     {
         var packageList = new List<NewMailItemPackage>();
 
-        // Create MailCopy from metadata only - NO MIME download
-        var mailCopy = await CreateMinimalMailCopyAsync(message, assignedFolder, cancellationToken);
+        // Create base MailCopy from metadata only - NO MIME download
+        var baseMailCopy = await CreateMinimalMailCopyAsync(message, assignedFolder, cancellationToken);
 
         // Check for local draft mapping using X-Wino-Draft-Id header from metadata
-        if (mailCopy.IsDraft)
+        if (baseMailCopy.IsDraft)
         {
             var draftIdHeader = message.Payload?.Headers?.FirstOrDefault(h => h.Name.Equals(Domain.Constants.WinoLocalDraftHeader, StringComparison.OrdinalIgnoreCase))?.Value;
 
@@ -1696,7 +1797,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
                 // This message belongs to existing local draft copy.
                 // We don't need to create a new mail copy for this message, just update the existing one.
 
-                bool isMappingSuccesfull = await _gmailChangeProcessor.MapLocalDraftAsync(Account.Id, localDraftCopyUniqueId, mailCopy.Id, mailCopy.DraftId, mailCopy.ThreadId);
+                bool isMappingSuccesfull = await _gmailChangeProcessor.MapLocalDraftAsync(Account.Id, localDraftCopyUniqueId, baseMailCopy.Id, baseMailCopy.DraftId, baseMailCopy.ThreadId);
 
                 if (isMappingSuccesfull) return null;
 
@@ -1704,12 +1805,32 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             }
         }
 
+        // For Gmail, a single mail can have multiple labels (folders).
+        // Each label requires a separate MailCopy entry in the database with:
+        // - Same Id, UniqueId, FileId (shared across all copies)
+        // - Different FolderId (one per label)
+        // ARCHIVE label is excluded here as it's virtual and handled by MapArchivedMailsAsync
         if (message.LabelIds is not null)
         {
+            // Generate shared identifiers that will be the same for all copies of this mail
+            var sharedId = baseMailCopy.Id;
+            var sharedFileId = baseMailCopy.FileId;
+
             foreach (var labelId in message.LabelIds)
             {
+                // Skip ARCHIVE label - it's virtual and handled separately
+                if (labelId == ServiceConstants.ARCHIVE_LABEL_ID)
+                    continue;
+
+                // Create a new MailCopy instance for each label to avoid shared reference issues
+                var mailCopyForLabel = await CreateMinimalMailCopyAsync(message, assignedFolder, cancellationToken);
+                
+                // Ensure all copies share the same Id and FileId
+                mailCopyForLabel.Id = sharedId;
+                mailCopyForLabel.FileId = sharedFileId;
+
                 // Pass null for MimeMessage - it will be downloaded later when user reads the mail
-                packageList.Add(new NewMailItemPackage(mailCopy, null, labelId));
+                packageList.Add(new NewMailItemPackage(mailCopyForLabel, null, labelId));
             }
         }
 
@@ -1807,7 +1928,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
 
         // Create a patch event to update only the attendee response
         var patchEvent = new Event();
-        
+
         // We need to get the event first to update the specific attendee
         // However, for efficiency, we'll use the patch method with sendUpdates parameter
         var patchRequest = _calendarService.Events.Patch(new Event
@@ -1824,8 +1945,8 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
         }, calendar.RemoteCalendarId, calendarItem.RemoteEventId);
 
         // Send updates to other attendees if there's a message
-        patchRequest.SendUpdates = !string.IsNullOrEmpty(request.ResponseMessage) 
-            ? Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.All 
+        patchRequest.SendUpdates = !string.IsNullOrEmpty(request.ResponseMessage)
+            ? Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.All
             : Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.None;
 
         return [new HttpRequestBundle<IClientServiceRequest>(patchRequest, request)];
@@ -1861,8 +1982,8 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             }
         }, calendar.RemoteCalendarId, calendarItem.RemoteEventId);
 
-        patchRequest.SendUpdates = !string.IsNullOrEmpty(request.ResponseMessage) 
-            ? Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.All 
+        patchRequest.SendUpdates = !string.IsNullOrEmpty(request.ResponseMessage)
+            ? Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.All
             : Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.None;
 
         return [new HttpRequestBundle<IClientServiceRequest>(patchRequest, request)];
@@ -1898,8 +2019,8 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             }
         }, calendar.RemoteCalendarId, calendarItem.RemoteEventId);
 
-        patchRequest.SendUpdates = !string.IsNullOrEmpty(request.ResponseMessage) 
-            ? Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.All 
+        patchRequest.SendUpdates = !string.IsNullOrEmpty(request.ResponseMessage)
+            ? Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.All
             : Google.Apis.Calendar.v3.EventsResource.PatchRequest.SendUpdatesEnum.None;
 
         return [new HttpRequestBundle<IClientServiceRequest>(patchRequest, request)];
@@ -1979,8 +2100,8 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
         var updateRequest = _calendarService.Events.Update(googleEvent, calendar.RemoteCalendarId, calendarItem.RemoteEventId);
 
         // Send notifications to attendees if the event has attendees
-        updateRequest.SendUpdates = (attendees != null && attendees.Count > 0) 
-            ? Google.Apis.Calendar.v3.EventsResource.UpdateRequest.SendUpdatesEnum.All 
+        updateRequest.SendUpdates = (attendees != null && attendees.Count > 0)
+            ? Google.Apis.Calendar.v3.EventsResource.UpdateRequest.SendUpdatesEnum.All
             : Google.Apis.Calendar.v3.EventsResource.UpdateRequest.SendUpdatesEnum.None;
 
         return [new HttpRequestBundle<IClientServiceRequest>(updateRequest, request)];

Wino.Core/Synchronizers/ImapSync/UnifiedImapSynchronizer.cs

@@ -0,0 +1,473 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Threading;
+using System.Threading.Tasks;
+using MailKit;
+using MailKit.Net.Imap;
+using MailKit.Search;
+using MoreLinq;
+using Serilog;
+using Wino.Core.Domain.Entities.Mail;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.MailItem;
+using Wino.Core.Domain.Models.Synchronization;
+using Wino.Core.Integration;
+using Wino.Services.Extensions;
+using IMailService = Wino.Core.Domain.Interfaces.IMailService;
+
+namespace Wino.Core.Synchronizers.ImapSync;
+
+/// <summary>
+/// Unified IMAP synchronization strategy that automatically selects the best available method:
+/// 1. QRESYNC (RFC 5162) - Best: supports quick resync with vanished messages
+/// 2. CONDSTORE (RFC 4551) - Good: supports mod-seq based change tracking
+/// 3. UID-based - Fallback: basic UID comparison
+///
+/// This consolidates the previous QResyncSynchronizer, CondstoreSynchronizer, and UidBasedSynchronizer
+/// into a single, enterprise-grade implementation with proper error handling and partial failure support.
+/// </summary>
+public class UnifiedImapSynchronizer
+{
+    private readonly ILogger _logger = Log.ForContext<UnifiedImapSynchronizer>();
+    private readonly IFolderService _folderService;
+    private readonly IMailService _mailService;
+    private readonly IImapSynchronizerErrorHandlerFactory _errorHandlerFactory;
+
+    // Minimum summary items to Fetch for mail synchronization from IMAP.
+    private readonly MessageSummaryItems MailSynchronizationFlags =
+        MessageSummaryItems.Flags |
+        MessageSummaryItems.UniqueId |
+        MessageSummaryItems.ThreadId |
+        MessageSummaryItems.EmailId |
+        MessageSummaryItems.Headers |
+        MessageSummaryItems.PreviewText |
+        MessageSummaryItems.GMailThreadId |
+        MessageSummaryItems.References |
+        MessageSummaryItems.ModSeq;
+
+    public UnifiedImapSynchronizer(
+        IFolderService folderService,
+        IMailService mailService,
+        IImapSynchronizerErrorHandlerFactory errorHandlerFactory)
+    {
+        _folderService = folderService;
+        _mailService = mailService;
+        _errorHandlerFactory = errorHandlerFactory;
+    }
+
+    /// <summary>
+    /// Determines the best synchronization strategy based on server capabilities.
+    /// </summary>
+    public ImapSyncStrategy DetermineSyncStrategy(IImapClient client)
+    {
+        if (client is WinoImapClient winoClient &&
+            client.Capabilities.HasFlag(ImapCapabilities.QuickResync) &&
+            winoClient.IsQResyncEnabled)
+        {
+            return ImapSyncStrategy.QResync;
+        }
+
+        if (client.Capabilities.HasFlag(ImapCapabilities.CondStore))
+        {
+            return ImapSyncStrategy.Condstore;
+        }
+
+        return ImapSyncStrategy.UidBased;
+    }
+
+    /// <summary>
+    /// Main synchronization entry point. Automatically selects the best strategy.
+    /// </summary>
+    public async Task<FolderSyncResult> SynchronizeFolderAsync(
+        IImapClient client,
+        MailItemFolder folder,
+        IImapSynchronizer synchronizer,
+        CancellationToken cancellationToken = default)
+    {
+        var strategy = DetermineSyncStrategy(client);
+        _logger.Debug("Using {Strategy} sync strategy for folder {FolderName}", strategy, folder.FolderName);
+
+        try
+        {
+            var downloadedIds = strategy switch
+            {
+                ImapSyncStrategy.QResync => await SynchronizeWithQResyncAsync(client, folder, synchronizer, cancellationToken),
+                ImapSyncStrategy.Condstore => await SynchronizeWithCondstoreAsync(client, folder, synchronizer, cancellationToken),
+                _ => await SynchronizeWithUidBasedAsync(client, folder, synchronizer, cancellationToken)
+            };
+
+            return FolderSyncResult.Successful(folder.Id, folder.FolderName, downloadedIds.Count);
+        }
+        catch (FolderNotFoundException)
+        {
+            _logger.Warning("Folder {FolderName} not found on server, deleting locally", folder.FolderName);
+            await _folderService.DeleteFolderAsync(folder.MailAccountId, folder.RemoteFolderId).ConfigureAwait(false);
+
+            return FolderSyncResult.Skipped(folder.Id, folder.FolderName, "Folder not found on server");
+        }
+        catch (OperationCanceledException)
+        {
+            throw;
+        }
+        catch (Exception ex)
+        {
+            var errorContext = new SynchronizerErrorContext
+            {
+                ErrorMessage = ex.Message,
+                Exception = ex,
+                FolderId = folder.Id,
+                FolderName = folder.FolderName,
+                OperationType = "ImapFolderSync"
+            };
+
+            var handled = await _errorHandlerFactory.HandleErrorAsync(errorContext).ConfigureAwait(false);
+
+            if (errorContext.CanContinueSync)
+            {
+                _logger.Warning(ex, "Folder {FolderName} sync failed with recoverable error", folder.FolderName);
+                return FolderSyncResult.Failed(folder.Id, folder.FolderName, errorContext);
+            }
+
+            _logger.Error(ex, "Folder {FolderName} sync failed with fatal error", folder.FolderName);
+            throw;
+        }
+    }
+
+    #region QRESYNC Strategy
+
+    private async Task<List<string>> SynchronizeWithQResyncAsync(
+        IImapClient client,
+        MailItemFolder folder,
+        IImapSynchronizer synchronizer,
+        CancellationToken cancellationToken)
+    {
+        var downloadedMessageIds = new List<string>();
+
+        if (client is not WinoImapClient winoClient)
+            throw new InvalidOperationException("QRESYNC requires WinoImapClient");
+
+        IMailFolder remoteFolder = null;
+
+        try
+        {
+            remoteFolder = await client.GetFolderAsync(folder.RemoteFolderId, cancellationToken).ConfigureAwait(false);
+
+            var localHighestModSeq = (ulong)Math.Max(folder.HighestModeSeq, 1);
+            var allUids = await _folderService.GetKnownUidsForFolderAsync(folder.Id);
+            var allUniqueIds = allUids.Select(a => new UniqueId(a)).ToList();
+
+            // Subscribe to events before opening
+            remoteFolder.MessagesVanished += (s, e) => HandleMessagesVanished(folder, e.UniqueIds);
+            remoteFolder.MessageFlagsChanged += (s, e) => HandleMessageFlagsChanged(folder, e.UniqueId, e.Flags);
+
+            // Open with QRESYNC parameters
+            await remoteFolder.OpenAsync(FolderAccess.ReadOnly, folder.UidValidity, localHighestModSeq, allUniqueIds, cancellationToken).ConfigureAwait(false);
+
+            // Get changed UIDs
+            var changedUids = await remoteFolder.SearchAsync(SearchQuery.ChangedSince(localHighestModSeq), cancellationToken).ConfigureAwait(false);
+
+            downloadedMessageIds = await ProcessChangedUidsAsync(synchronizer, remoteFolder, folder, changedUids, cancellationToken).ConfigureAwait(false);
+
+            // Update folder tracking
+            folder.HighestModeSeq = unchecked((long)remoteFolder.HighestModSeq);
+            folder.UidValidity = remoteFolder.UidValidity;
+
+            // Handle deletions
+            await HandleDeletedMessagesAsync(folder, remoteFolder, cancellationToken).ConfigureAwait(false);
+
+            await _folderService.UpdateFolderAsync(folder).ConfigureAwait(false);
+        }
+        finally
+        {
+            if (remoteFolder?.IsOpen == true && !cancellationToken.IsCancellationRequested)
+            {
+                await remoteFolder.CloseAsync().ConfigureAwait(false);
+            }
+        }
+
+        return downloadedMessageIds;
+    }
+
+    #endregion
+
+    #region CONDSTORE Strategy
+
+    private async Task<List<string>> SynchronizeWithCondstoreAsync(
+        IImapClient client,
+        MailItemFolder folder,
+        IImapSynchronizer synchronizer,
+        CancellationToken cancellationToken)
+    {
+        var downloadedMessageIds = new List<string>();
+        IMailFolder remoteFolder = null;
+
+        try
+        {
+            remoteFolder = await client.GetFolderAsync(folder.RemoteFolderId, cancellationToken).ConfigureAwait(false);
+            await remoteFolder.OpenAsync(FolderAccess.ReadOnly, cancellationToken).ConfigureAwait(false);
+
+            var localHighestModSeq = (ulong)folder.HighestModeSeq;
+            bool isInitialSync = localHighestModSeq == 0;
+
+            if (remoteFolder.HighestModSeq > localHighestModSeq || isInitialSync)
+            {
+                IList<UniqueId> changedUids;
+
+                // Use SORT if available for better ordering
+                if (client.Capabilities.HasFlag(ImapCapabilities.Sort))
+                {
+                    changedUids = await remoteFolder.SortAsync(
+                        SearchQuery.ChangedSince(Math.Max(localHighestModSeq, 1)),
+                        [OrderBy.ReverseDate],
+                        cancellationToken).ConfigureAwait(false);
+                }
+                else
+                {
+                    changedUids = await remoteFolder.SearchAsync(
+                        SearchQuery.ChangedSince(Math.Max(localHighestModSeq, 1)),
+                        cancellationToken).ConfigureAwait(false);
+                }
+
+                // For initial sync, limit the number of messages
+                if (isInitialSync)
+                {
+                    changedUids = changedUids
+                        .OrderByDescending(a => a.Id)
+                        .Take((int)synchronizer.InitialMessageDownloadCountPerFolder)
+                        .ToList();
+                }
+
+                downloadedMessageIds = await ProcessChangedUidsAsync(synchronizer, remoteFolder, folder, changedUids, cancellationToken).ConfigureAwait(false);
+
+                folder.HighestModeSeq = unchecked((long)remoteFolder.HighestModSeq);
+                await _folderService.UpdateFolderAsync(folder).ConfigureAwait(false);
+            }
+
+            await HandleDeletedMessagesAsync(folder, remoteFolder, cancellationToken).ConfigureAwait(false);
+        }
+        finally
+        {
+            if (remoteFolder?.IsOpen == true && !cancellationToken.IsCancellationRequested)
+            {
+                await remoteFolder.CloseAsync(cancellationToken: cancellationToken).ConfigureAwait(false);
+            }
+        }
+
+        return downloadedMessageIds;
+    }
+
+    #endregion
+
+    #region UID-Based Strategy (Fallback)
+
+    private async Task<List<string>> SynchronizeWithUidBasedAsync(
+        IImapClient client,
+        MailItemFolder folder,
+        IImapSynchronizer synchronizer,
+        CancellationToken cancellationToken)
+    {
+        var downloadedMessageIds = new List<string>();
+        IMailFolder remoteFolder = null;
+
+        try
+        {
+            remoteFolder = await client.GetFolderAsync(folder.RemoteFolderId, cancellationToken).ConfigureAwait(false);
+            await remoteFolder.OpenAsync(FolderAccess.ReadOnly, cancellationToken).ConfigureAwait(false);
+
+            // Get all remote UIDs and take the most recent ones
+            var remoteUids = await remoteFolder.SearchAsync(SearchQuery.All, cancellationToken).ConfigureAwait(false);
+            var limitedUids = remoteUids
+                .OrderByDescending(a => a.Id)
+                .Take((int)synchronizer.InitialMessageDownloadCountPerFolder)
+                .ToList();
+
+            downloadedMessageIds = await ProcessChangedUidsAsync(synchronizer, remoteFolder, folder, limitedUids, cancellationToken).ConfigureAwait(false);
+
+            await HandleDeletedMessagesAsync(folder, remoteFolder, cancellationToken).ConfigureAwait(false);
+        }
+        finally
+        {
+            if (remoteFolder?.IsOpen == true && !cancellationToken.IsCancellationRequested)
+            {
+                await remoteFolder.CloseAsync(cancellationToken: cancellationToken).ConfigureAwait(false);
+            }
+        }
+
+        return downloadedMessageIds;
+    }
+
+    #endregion
+
+    #region Shared Processing Methods
+
+    private async Task<List<string>> ProcessChangedUidsAsync(
+        IImapSynchronizer synchronizer,
+        IMailFolder remoteFolder,
+        MailItemFolder localFolder,
+        IList<UniqueId> changedUids,
+        CancellationToken cancellationToken)
+    {
+        var downloadedMessageIds = new List<string>();
+
+        if (changedUids == null || changedUids.Count == 0)
+            return downloadedMessageIds;
+
+        // Get existing mails to determine what's new vs. updated
+        var existingMails = await _mailService.GetExistingMailsAsync(localFolder.Id, changedUids).ConfigureAwait(false);
+        var existingMailUids = existingMails.Select(m => MailkitClientExtensions.ResolveUidStruct(m.Id)).ToArray();
+
+        var newMessageUids = changedUids.Except(existingMailUids).ToList();
+
+        // Update flags for existing mails
+        if (existingMailUids.Any())
+        {
+            var existingFlagData = await remoteFolder.FetchAsync(existingMailUids, MessageSummaryItems.Flags | MessageSummaryItems.UniqueId, cancellationToken).ConfigureAwait(false);
+
+            foreach (var update in existingFlagData)
+            {
+                if (update.UniqueId == UniqueId.Invalid || update.Flags == null) continue;
+
+                var existingMail = existingMails.FirstOrDefault(m => MailkitClientExtensions.ResolveUidStruct(m.Id).Id == update.UniqueId.Id);
+                if (existingMail != null)
+                {
+                    await UpdateMailFlagsAsync(existingMail, update.Flags.Value).ConfigureAwait(false);
+                }
+            }
+        }
+
+        // Download new messages in batches
+        var batches = newMessageUids.Batch(50);
+        foreach (var batch in batches)
+        {
+            cancellationToken.ThrowIfCancellationRequested();
+
+            var batchList = batch.ToList();
+            downloadedMessageIds.AddRange(batchList.Select(uid => MailkitClientExtensions.CreateUid(localFolder.Id, uid.Id)));
+
+            await DownloadMessagesAsync(synchronizer, remoteFolder, localFolder, new UniqueIdSet(batchList, SortOrder.Ascending), cancellationToken).ConfigureAwait(false);
+        }
+
+        return downloadedMessageIds;
+    }
+
+    private async Task DownloadMessagesAsync(
+        IImapSynchronizer synchronizer,
+        IMailFolder folder,
+        MailItemFolder localFolder,
+        UniqueIdSet uniqueIdSet,
+        CancellationToken cancellationToken)
+    {
+        var summaries = await folder.FetchAsync(uniqueIdSet, MailSynchronizationFlags, cancellationToken).ConfigureAwait(false);
+
+        foreach (var summary in summaries)
+        {
+            try
+            {
+                var mimeMessage = await folder.GetMessageAsync(summary.UniqueId, cancellationToken).ConfigureAwait(false);
+                var creationPackage = new ImapMessageCreationPackage(summary, mimeMessage);
+                var mailPackages = await synchronizer.CreateNewMailPackagesAsync(creationPackage, localFolder, cancellationToken).ConfigureAwait(false);
+
+                if (mailPackages != null)
+                {
+                    foreach (var package in mailPackages)
+                    {
+                        if (package != null)
+                        {
+                            await _mailService.CreateMailAsync(localFolder.MailAccountId, package).ConfigureAwait(false);
+                        }
+                    }
+                }
+            }
+            catch (Exception ex)
+            {
+                _logger.Warning(ex, "Failed to download message {UniqueId} in folder {FolderName}", summary.UniqueId, localFolder.FolderName);
+                // Continue with other messages
+            }
+        }
+    }
+
+    private async Task HandleDeletedMessagesAsync(MailItemFolder localFolder, IMailFolder remoteFolder, CancellationToken cancellationToken)
+    {
+        var allLocalUids = (await _folderService.GetKnownUidsForFolderAsync(localFolder.Id)).Select(a => new UniqueId(a)).ToList();
+
+        if (allLocalUids.Count == 0) return;
+
+        var remoteAllUids = await remoteFolder.SearchAsync(SearchQuery.All, cancellationToken).ConfigureAwait(false);
+        var deletedUids = allLocalUids.Except(remoteAllUids).ToList();
+
+        foreach (var deletedUid in deletedUids)
+        {
+            var localMailCopyId = MailkitClientExtensions.CreateUid(localFolder.Id, deletedUid.Id);
+            await _mailService.DeleteMailAsync(localFolder.MailAccountId, localMailCopyId).ConfigureAwait(false);
+        }
+    }
+
+    private async Task UpdateMailFlagsAsync(MailCopy mailCopy, MessageFlags flags)
+    {
+        var isFlagged = MailkitClientExtensions.GetIsFlagged(flags);
+        var isRead = MailkitClientExtensions.GetIsRead(flags);
+
+        if (isFlagged != mailCopy.IsFlagged)
+        {
+            await _mailService.ChangeFlagStatusAsync(mailCopy.Id, isFlagged).ConfigureAwait(false);
+        }
+
+        if (isRead != mailCopy.IsRead)
+        {
+            await _mailService.ChangeReadStatusAsync(mailCopy.Id, isRead).ConfigureAwait(false);
+        }
+    }
+
+    private void HandleMessagesVanished(MailItemFolder folder, IList<UniqueId> uniqueIds)
+    {
+        // Fire and forget - these are event handlers
+        _ = Task.Run(async () =>
+        {
+            foreach (var uniqueId in uniqueIds)
+            {
+                var localMailCopyId = MailkitClientExtensions.CreateUid(folder.Id, uniqueId.Id);
+                await _mailService.DeleteMailAsync(folder.MailAccountId, localMailCopyId).ConfigureAwait(false);
+            }
+        });
+    }
+
+    private void HandleMessageFlagsChanged(MailItemFolder folder, UniqueId? uniqueId, MessageFlags flags)
+    {
+        if (uniqueId == null) return;
+
+        _ = Task.Run(async () =>
+        {
+            var localMailCopyId = MailkitClientExtensions.CreateUid(folder.Id, uniqueId.Value.Id);
+            var isFlagged = MailkitClientExtensions.GetIsFlagged(flags);
+            var isRead = MailkitClientExtensions.GetIsRead(flags);
+
+            await _mailService.ChangeReadStatusAsync(localMailCopyId, isRead).ConfigureAwait(false);
+            await _mailService.ChangeFlagStatusAsync(localMailCopyId, isFlagged).ConfigureAwait(false);
+        });
+    }
+
+    #endregion
+}
+
+/// <summary>
+/// IMAP synchronization strategy enumeration.
+/// </summary>
+public enum ImapSyncStrategy
+{
+    /// <summary>
+    /// RFC 5162 Quick Resync - supports vanished messages and efficient delta sync.
+    /// </summary>
+    QResync,
+
+    /// <summary>
+    /// RFC 4551 Conditional Store - supports mod-seq based change tracking.
+    /// </summary>
+    Condstore,
+
+    /// <summary>
+    /// Basic UID-based synchronization - fallback for servers without advanced features.
+    /// </summary>
+    UidBased
+}

Wino.Core/Synchronizers/ImapSynchronizer.cs

@@ -26,6 +26,7 @@ using Wino.Core.Integration.Processors;
 using Wino.Core.Requests.Bundles;
 using Wino.Core.Requests.Folder;
 using Wino.Core.Requests.Mail;
+using Wino.Core.Synchronizers.ImapSync;
 using Wino.Messaging.Server;
 using Wino.Messaging.UI;
 using Wino.Services.Extensions;
@@ -52,16 +53,22 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
     private readonly IImapChangeProcessor _imapChangeProcessor;
     private readonly IImapSynchronizationStrategyProvider _imapSynchronizationStrategyProvider;
     private readonly IApplicationConfiguration _applicationConfiguration;
+    private readonly UnifiedImapSynchronizer _unifiedSynchronizer;
+    private readonly IImapSynchronizerErrorHandlerFactory _errorHandlerFactory;
 
     public ImapSynchronizer(MailAccount account,
                             IImapChangeProcessor imapChangeProcessor,
                             IImapSynchronizationStrategyProvider imapSynchronizationStrategyProvider,
-                            IApplicationConfiguration applicationConfiguration) : base(account, WeakReferenceMessenger.Default)
+                            IApplicationConfiguration applicationConfiguration,
+                            UnifiedImapSynchronizer unifiedSynchronizer,
+                            IImapSynchronizerErrorHandlerFactory errorHandlerFactory) : base(account, WeakReferenceMessenger.Default)
     {
         // Create client pool with account protocol log.
         _imapChangeProcessor = imapChangeProcessor;
         _imapSynchronizationStrategyProvider = imapSynchronizationStrategyProvider;
         _applicationConfiguration = applicationConfiguration;
+        _unifiedSynchronizer = unifiedSynchronizer;
+        _errorHandlerFactory = errorHandlerFactory;
 
         var protocolLogStream = CreateAccountProtocolLogFileStream();
         var poolOptions = ImapClientPoolOptions.CreateDefault(Account.ServerInformation, protocolLogStream);
@@ -303,53 +310,130 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
     protected override async Task<MailSynchronizationResult> SynchronizeMailsInternalAsync(MailSynchronizationOptions options, CancellationToken cancellationToken = default)
     {
         var downloadedMessageIds = new List<string>();
+        var folderResults = new List<FolderSyncResult>();
 
         _logger.Information("Internal synchronization started for {Name}", Account.Name);
         _logger.Information("Options: {Options}", options);
 
-        // Set indeterminate progress initially
-        UpdateSyncProgress(0, 0, "Synchronizing...");
-
-        bool shouldDoFolderSync = options.Type == MailSynchronizationType.FullFolders || options.Type == MailSynchronizationType.FoldersOnly;
-
-        if (shouldDoFolderSync)
+        try
         {
-            await SynchronizeFoldersAsync(cancellationToken).ConfigureAwait(false);
-        }
+            // Set indeterminate progress initially
+            UpdateSyncProgress(0, 0, "Synchronizing...");
 
-        if (options.Type != MailSynchronizationType.FoldersOnly)
-        {
-            var synchronizationFolders = await _imapChangeProcessor.GetSynchronizationFoldersAsync(options).ConfigureAwait(false);
+            bool shouldDoFolderSync = options.Type == MailSynchronizationType.FullFolders || options.Type == MailSynchronizationType.FoldersOnly;
 
-            var totalFolders = synchronizationFolders.Count;
-
-            for (int i = 0; i < totalFolders; i++)
+            if (shouldDoFolderSync)
             {
-                var folder = synchronizationFolders[i];
+                await SynchronizeFoldersAsync(cancellationToken).ConfigureAwait(false);
+            }
 
-                // Update progress based on folder completion
-                UpdateSyncProgress(totalFolders, totalFolders - (i + 1), $"Syncing {folder.FolderName}...");
+            if (options.Type != MailSynchronizationType.FoldersOnly)
+            {
+                var synchronizationFolders = await _imapChangeProcessor.GetSynchronizationFoldersAsync(options).ConfigureAwait(false);
 
-                var folderDownloadedMessageIds = await SynchronizeFolderInternalAsync(folder, cancellationToken).ConfigureAwait(false);
+                var totalFolders = synchronizationFolders.Count;
 
-                if (cancellationToken.IsCancellationRequested) return MailSynchronizationResult.Canceled;
-
-                if (folderDownloadedMessageIds != null)
+                for (int i = 0; i < totalFolders; i++)
                 {
-                    downloadedMessageIds.AddRange(folderDownloadedMessageIds);
+                    var folder = synchronizationFolders[i];
+
+                    // Update progress based on folder completion
+                    UpdateSyncProgress(totalFolders, totalFolders - (i + 1), $"Syncing {folder.FolderName}...");
+
+                    try
+                    {
+                        // Use the unified synchronizer for folder sync
+                        IImapClient client = null;
+
+                        try
+                        {
+                            client = await _clientPool.GetClientAsync().ConfigureAwait(false);
+                            var folderResult = await _unifiedSynchronizer.SynchronizeFolderAsync(client, folder, this, cancellationToken).ConfigureAwait(false);
+                            folderResults.Add(folderResult);
+
+                            if (folderResult.Success && folderResult.DownloadedCount > 0)
+                            {
+                                // Get the downloaded message IDs for this folder
+                                var folderDownloadedIds = await GetDownloadedIdsForFolderAsync(folder, folderResult.DownloadedCount).ConfigureAwait(false);
+                                downloadedMessageIds.AddRange(folderDownloadedIds);
+                            }
+                        }
+                        finally
+                        {
+                            if (client != null)
+                            {
+                                _clientPool.Release(client);
+                            }
+                        }
+                    }
+                    catch (OperationCanceledException)
+                    {
+                        throw;
+                    }
+                    catch (Exception ex)
+                    {
+                        var errorContext = new SynchronizerErrorContext
+                        {
+                            Account = Account,
+                            ErrorMessage = ex.Message,
+                            Exception = ex,
+                            FolderId = folder.Id,
+                            FolderName = folder.FolderName,
+                            OperationType = "ImapFolderSync"
+                        };
+
+                        var handled = await _errorHandlerFactory.HandleErrorAsync(errorContext).ConfigureAwait(false);
+
+                        if (errorContext.CanContinueSync)
+                        {
+                            _logger.Warning(ex, "Folder {FolderName} sync failed, continuing with other folders", folder.FolderName);
+                            folderResults.Add(FolderSyncResult.Failed(folder.Id, folder.FolderName, errorContext));
+                        }
+                        else
+                        {
+                            _logger.Error(ex, "Folder {FolderName} sync failed with fatal error", folder.FolderName);
+                            folderResults.Add(FolderSyncResult.Failed(folder.Id, folder.FolderName, errorContext));
+                            throw;
+                        }
+                    }
+
+                    if (cancellationToken.IsCancellationRequested) return MailSynchronizationResult.Canceled;
                 }
             }
         }
-
-        // Reset progress
-        ResetSyncProgress();
+        catch (OperationCanceledException)
+        {
+            _logger.Information("Synchronization was canceled for {Name}", Account.Name);
+            return MailSynchronizationResult.Canceled;
+        }
+        catch (Exception ex)
+        {
+            _logger.Error(ex, "Synchronization failed for {Name}", Account.Name);
+            return MailSynchronizationResult.Failed(ex);
+        }
+        finally
+        {
+            // Reset progress
+            ResetSyncProgress();
+        }
 
         // Get all unread new downloaded items and return in the result.
         // This is primarily used in notifications.
 
         var unreadNewItems = await _imapChangeProcessor.GetDownloadedUnreadMailsAsync(Account.Id, downloadedMessageIds).ConfigureAwait(false);
 
-        return MailSynchronizationResult.Completed(unreadNewItems);
+        return MailSynchronizationResult.CompletedWithFolderResults(unreadNewItems, folderResults);
+    }
+
+    /// <summary>
+    /// Gets the most recent downloaded message IDs for a folder.
+    /// Used for notification purposes after sync completes.
+    /// </summary>
+    private async Task<List<string>> GetDownloadedIdsForFolderAsync(MailItemFolder folder, int count)
+    {
+        // Get the most recent mail IDs from the folder
+        var recentMails = await _imapChangeProcessor.GetRecentMailIdsForFolderAsync(folder.Id, count).ConfigureAwait(false);
+        return recentMails?.ToList() ?? new List<string>();
     }
 
     public override async Task ExecuteNativeRequestsAsync(List<IRequestBundle<ImapRequest>> batchedRequests, CancellationToken cancellationToken = default)

Wino.Core/Synchronizers/OutlookSynchronizer.cs

@@ -30,7 +30,6 @@ using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Exceptions;
 using Wino.Core.Domain.Interfaces;
 using Wino.Core.Domain.Models.Accounts;
-using Wino.Core.Domain.Models.Errors;
 using Wino.Core.Domain.Models.Folders;
 using Wino.Core.Domain.Models.MailItem;
 using Wino.Core.Domain.Models.Synchronization;
@@ -141,6 +140,7 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
     protected override async Task<MailSynchronizationResult> SynchronizeMailsInternalAsync(MailSynchronizationOptions options, CancellationToken cancellationToken = default)
     {
         var downloadedMessageIds = new List<string>();
+        var folderResults = new List<FolderSyncResult>();
 
         _logger.Information("Internal synchronization started for {Name}", Account.Name);
         _logger.Information("Options: {Options}", options);
@@ -169,17 +169,77 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
                     var statusMessage = string.Format(Translator.Sync_SynchronizingFolder, folder.FolderName, progressPercentage);
                     UpdateSyncProgress(totalFolders, totalFolders - (i + 1), statusMessage);
 
-                    var folderDownloadedMessageIds = await SynchronizeFolderAsync(folder, cancellationToken).ConfigureAwait(false);
-                    downloadedMessageIds.AddRange(folderDownloadedMessageIds);
+                    try
+                    {
+                        var folderDownloadedMessageIds = await SynchronizeFolderAsync(folder, cancellationToken).ConfigureAwait(false);
+                        downloadedMessageIds.AddRange(folderDownloadedMessageIds);
+
+                        folderResults.Add(FolderSyncResult.Successful(folder.Id, folder.FolderName, folderDownloadedMessageIds.Count()));
+                    }
+                    catch (OperationCanceledException)
+                    {
+                        // Cancellation should stop the entire sync
+                        throw;
+                    }
+                    catch (ODataError odataError)
+                    {
+                        // Handle OData errors - determine if we should continue or stop
+                        var errorContext = new SynchronizerErrorContext
+                        {
+                            Account = Account,
+                            ErrorCode = (int?)odataError.ResponseStatusCode,
+                            ErrorMessage = odataError.Error?.Message ?? odataError.Message,
+                            Exception = odataError,
+                            FolderId = folder.Id,
+                            FolderName = folder.FolderName,
+                            OperationType = "FolderSync"
+                        };
+
+                        var handled = await _errorHandlingFactory.HandleErrorAsync(errorContext).ConfigureAwait(false);
+
+                        if (errorContext.CanContinueSync)
+                        {
+                            _logger.Warning("Folder {FolderName} sync failed with recoverable error, continuing with other folders. Error: {Error}",
+                                folder.FolderName, odataError.Error?.Message);
+                            folderResults.Add(FolderSyncResult.Failed(folder.Id, folder.FolderName, errorContext));
+                        }
+                        else
+                        {
+                            _logger.Error(odataError, "Folder {FolderName} sync failed with fatal error, stopping sync", folder.FolderName);
+                            folderResults.Add(FolderSyncResult.Failed(folder.Id, folder.FolderName, errorContext));
+                            throw;
+                        }
+                    }
+                    catch (Exception ex)
+                    {
+                        // For unexpected exceptions, try to classify and decide if we should continue
+                        var errorContext = new SynchronizerErrorContext
+                        {
+                            Account = Account,
+                            ErrorMessage = ex.Message,
+                            Exception = ex,
+                            FolderId = folder.Id,
+                            FolderName = folder.FolderName,
+                            OperationType = "FolderSync",
+                            Severity = SynchronizerErrorSeverity.Recoverable, // Default to recoverable for individual folders
+                            Category = SynchronizerErrorCategory.Unknown
+                        };
+
+                        _logger.Warning(ex, "Folder {FolderName} sync failed, continuing with other folders", folder.FolderName);
+                        folderResults.Add(FolderSyncResult.Failed(folder.Id, folder.FolderName, errorContext));
+                    }
                 }
             }
         }
+        catch (OperationCanceledException)
+        {
+            _logger.Information("Synchronization was canceled for {Name}", Account.Name);
+            return MailSynchronizationResult.Canceled;
+        }
         catch (Exception ex)
         {
             _logger.Error(ex, "Synchronizing folders for {Name}", Account.Name);
-            Debugger.Break();
-
-            throw;
+            return MailSynchronizationResult.Failed(ex);
         }
         finally
         {
@@ -187,12 +247,12 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
             ResetSyncProgress();
         }
 
-        // Get all unred new downloaded items and return in the result.
+        // Get all unread new downloaded items and return in the result.
         // This is primarily used in notifications.
 
         var unreadNewItems = await _outlookChangeProcessor.GetDownloadedUnreadMailsAsync(Account.Id, downloadedMessageIds).ConfigureAwait(false);
 
-        return MailSynchronizationResult.Completed(unreadNewItems);
+        return MailSynchronizationResult.CompletedWithFolderResults(unreadNewItems, folderResults);
     }
 
     public async Task DownloadSearchResultMessageAsync(string messageId, MailItemFolder assignedFolder, CancellationToken cancellationToken = default)

Wino.Core/Wino.Core.csproj

@@ -39,4 +39,8 @@
 		<ProjectReference Include="..\Wino.Messages\Wino.Messaging.csproj" />
 		<ProjectReference Include="..\Wino.Services\Wino.Services.csproj" />
 	</ItemGroup>
+	
+	<ItemGroup>
+	  <Folder Include="Domain\Models\Errors\" />
+	</ItemGroup>
 </Project>

Wino.Mail.ViewModels/MailListPageViewModel.cs

@@ -670,7 +670,7 @@ public partial class MailListPageViewModel : MailBaseViewModel,
 
         await MailCollection.UpdateMailCopy(updatedMail, source);
 
-        await ExecuteUIThread(() => { SetupTopBarActions(); });
+        // await ExecuteUIThread(() => { SetupTopBarActions(); });
     }
 
     protected override async void OnMailRemoved(MailCopy removedMail)

Wino.Services/AccountService.cs

@@ -599,4 +599,24 @@ public class AccountService : BaseDatabaseService, IAccountService
 
         return account?.Preferences?.IsNotificationsEnabled ?? false;
     }
+
+    public async Task UpdateLastFolderStructureSyncDateAsync(Guid accountId)
+    {
+        var account = await GetAccountAsync(accountId);
+        if (account == null) return;
+
+        account.LastFolderStructureSyncDate = DateTime.UtcNow;
+        await Connection.UpdateAsync(account, typeof(MailAccount)).ConfigureAwait(false);
+    }
+
+    public async Task<bool> ShouldSyncFolderStructureAsync(Guid accountId, TimeSpan syncInterval)
+    {
+        var account = await GetAccountAsync(accountId);
+        if (account == null) return true;
+
+        if (!account.LastFolderStructureSyncDate.HasValue)
+            return true;
+
+        return DateTime.UtcNow - account.LastFolderStructureSyncDate.Value > syncInterval;
+    }
 }

Wino.Services/MailService.cs

@@ -1124,6 +1124,18 @@ public class MailService : BaseDatabaseService, IMailService
         return new GmailArchiveComparisonResult(addedMails, removedMails);
     }
 
+    public async Task<IEnumerable<string>> GetRecentMailIdsForFolderAsync(Guid folderId, int count)
+    {
+        var recentMails = await Connection.Table<MailCopy>()
+            .Where(a => a.FolderId == folderId)
+            .OrderByDescending(a => a.CreationDate)
+            .Take(count)
+            .ToListAsync()
+            .ConfigureAwait(false);
+
+        return recentMails.Select(m => m.Id);
+    }
+
     public async Task<List<MailCopy>> GetMailItemsAsync(IEnumerable<string> mailCopyIds)
     {
         if (!mailCopyIds.Any()) return [];