Add read receipt tracking for sent mail

Wino.Core.Domain/Constants.cs

@@ -6,6 +6,8 @@ public static class Constants
     /// MIME header that exists in all the drafts created from Wino.
     /// </summary>
     public const string WinoLocalDraftHeader = "X-Wino-Draft-Id";
+    public const string DispositionNotificationToHeader = "Disposition-Notification-To";
+    public const string OriginalMessageIdHeader = "Original-Message-ID";
     public const string LocalDraftStartPrefix = "localDraft_";
 
     public const string CalendarEventRecurrenceRuleSeperator = "___";

Wino.Core.Domain/Entities/Mail/MailCopy.cs

@@ -155,6 +155,18 @@ public class MailCopy
     [Ignore]
     public AccountContact SenderContact { get; set; }
 
+    [Ignore]
+    public bool IsReadReceiptRequested { get; set; }
+
+    [Ignore]
+    public SentMailReceiptStatus ReadReceiptStatus { get; set; }
+
+    [Ignore]
+    public DateTime? ReadReceiptAcknowledgedAtUtc { get; set; }
+
+    [Ignore]
+    public Guid? ReadReceiptMessageUniqueId { get; set; }
+
     public IEnumerable<Guid> GetContainingIds() => [UniqueId];
     public override string ToString() => $"{Subject} <-> {Id}";
 }

Wino.Core.Domain/Entities/Mail/SentMailReceiptState.cs

@@ -0,0 +1,25 @@
+using System;
+using SQLite;
+using Wino.Core.Domain.Enums;
+
+namespace Wino.Core.Domain.Entities.Mail;
+
+public class SentMailReceiptState
+{
+    [PrimaryKey]
+    public Guid MailUniqueId { get; set; }
+
+    public Guid AccountId { get; set; }
+
+    public string MessageId { get; set; }
+
+    public bool IsReceiptRequested { get; set; }
+
+    public DateTime RequestedAtUtc { get; set; }
+
+    public SentMailReceiptStatus Status { get; set; }
+
+    public DateTime? AcknowledgedAtUtc { get; set; }
+
+    public Guid? ReceiptMessageUniqueId { get; set; }
+}

Wino.Core.Domain/Enums/MailCopyChangeFlags.cs

@@ -30,6 +30,7 @@ public enum MailCopyChangeFlags
     AssignedAccount = 1 << 21,
     SenderContact = 1 << 22,
     UniqueId = 1 << 23,
+    ReadReceiptState = 1 << 24,
     All = Id |
           FolderId |
           ThreadId |
@@ -53,5 +54,6 @@ public enum MailCopyChangeFlags
           AssignedFolder |
           AssignedAccount |
           SenderContact |
-          UniqueId
+          UniqueId |
+          ReadReceiptState
 }

Wino.Core.Domain/Enums/SentMailReceiptStatus.cs

@@ -0,0 +1,9 @@
+namespace Wino.Core.Domain.Enums;
+
+public enum SentMailReceiptStatus
+{
+    None = 0,
+    Requested = 1,
+    Acknowledged = 2,
+    FailedToCorrelate = 3
+}

Wino.Core.Domain/Extensions/ReadReceiptExtensions.cs

@@ -0,0 +1,111 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using MimeKit;
+
+namespace Wino.Core.Domain.Extensions;
+
+public static class ReadReceiptExtensions
+{
+    public static bool HasReadReceiptRequest(this MimeMessage mimeMessage)
+        => mimeMessage?.Headers?.Contains(Constants.DispositionNotificationToHeader) == true
+           && !string.IsNullOrWhiteSpace(mimeMessage.Headers[Constants.DispositionNotificationToHeader]);
+
+    public static void SetReadReceiptRequest(this MimeMessage mimeMessage, string address, bool isRequested)
+    {
+        if (mimeMessage == null)
+            return;
+
+        mimeMessage.Headers.Remove(Constants.DispositionNotificationToHeader);
+
+        if (isRequested && !string.IsNullOrWhiteSpace(address))
+        {
+            mimeMessage.Headers.Add(Constants.DispositionNotificationToHeader, address.Trim());
+        }
+    }
+
+    public static bool LooksLikeReadReceipt(this MimeMessage mimeMessage)
+    {
+        if (mimeMessage?.Body == null)
+            return false;
+
+        return mimeMessage.BodyParts.Any(IsReadReceiptEntity) || IsReadReceiptEntity(mimeMessage.Body);
+    }
+
+    public static ReadReceiptParseResult ParseReadReceipt(this MimeMessage mimeMessage)
+    {
+        if (!mimeMessage.LooksLikeReadReceipt())
+            return ReadReceiptParseResult.Empty;
+
+        var entity = mimeMessage.BodyParts.FirstOrDefault(IsReadReceiptEntity) ?? mimeMessage.Body;
+        var lines = ReadEntityLines(entity);
+
+        string originalMessageId = null;
+
+        foreach (var line in lines)
+        {
+            if (line.StartsWith(Constants.OriginalMessageIdHeader + ":", StringComparison.OrdinalIgnoreCase))
+            {
+                originalMessageId = line.Substring(line.IndexOf(':') + 1).Trim();
+                break;
+            }
+        }
+
+        var acknowledgedAtUtc = mimeMessage.Date != DateTimeOffset.MinValue
+            ? mimeMessage.Date.UtcDateTime
+            : (DateTime?)null;
+
+        return new ReadReceiptParseResult(
+            true,
+            MailHeaderExtensions.NormalizeMessageId(originalMessageId),
+            acknowledgedAtUtc);
+    }
+
+    private static bool IsReadReceiptEntity(MimeEntity entity)
+    {
+        if (entity?.ContentType == null)
+            return false;
+
+        if (entity.ContentType.MimeType.Equals("message/disposition-notification", StringComparison.OrdinalIgnoreCase))
+            return true;
+
+        var reportType = entity.ContentType.Parameters["report-type"];
+        return entity.ContentType.MimeType.Equals("multipart/report", StringComparison.OrdinalIgnoreCase)
+               && !string.IsNullOrWhiteSpace(reportType)
+               && reportType.Equals("disposition-notification", StringComparison.OrdinalIgnoreCase);
+    }
+
+    private static IEnumerable<string> ReadEntityLines(MimeEntity entity)
+    {
+        if (entity is TextPart textPart)
+        {
+            return SplitLines(textPart.Text);
+        }
+
+        if (entity is MimePart mimePart)
+        {
+            using var memoryStream = new MemoryStream();
+            mimePart.Content?.DecodeTo(memoryStream);
+            memoryStream.Position = 0;
+            using var reader = new StreamReader(memoryStream);
+            return SplitLines(reader.ReadToEnd());
+        }
+
+        using var serializedStream = new MemoryStream();
+        entity.WriteTo(serializedStream);
+        serializedStream.Position = 0;
+        using var serializedReader = new StreamReader(serializedStream);
+        return SplitLines(serializedReader.ReadToEnd());
+    }
+
+    private static IEnumerable<string> SplitLines(string content)
+        => string.IsNullOrWhiteSpace(content)
+            ? []
+            : content.Split(["\r\n", "\n"], StringSplitOptions.RemoveEmptyEntries);
+}
+
+public sealed record ReadReceiptParseResult(bool IsReadReceipt, string OriginalMessageId, DateTime? AcknowledgedAtUtc)
+{
+    public static ReadReceiptParseResult Empty { get; } = new(false, string.Empty, null);
+}

Wino.Core.Domain/Interfaces/IMailItemDisplayInformation.cs

@@ -24,4 +24,7 @@ public interface IMailItemDisplayInformation : INotifyPropertyChanged
     bool ThumbnailUpdatedEvent { get; }
     bool IsThreadExpanded { get; }
     AccountContact SenderContact { get; }
+    bool HasReadReceiptTracking { get; }
+    bool IsReadReceiptAcknowledged { get; }
+    string ReadReceiptDisplayText { get; }
 }

Wino.Core.Domain/Interfaces/ISentMailReceiptService.cs

@@ -0,0 +1,15 @@
+using System;
+using System.Collections.Generic;
+using System.Threading.Tasks;
+using MimeKit;
+using Wino.Core.Domain.Entities.Mail;
+
+namespace Wino.Core.Domain.Interfaces;
+
+public interface ISentMailReceiptService
+{
+    Task PopulateReceiptStateAsync(MailCopy mailCopy);
+    Task PopulateReceiptStatesAsync(IReadOnlyCollection<MailCopy> mailCopies);
+    Task TrackSentMailAsync(MailCopy mailCopy, MimeMessage mimeMessage = null);
+    Task ProcessIncomingReceiptAsync(MailCopy receiptMail, MimeMessage mimeMessage);
+}

Wino.Core.Domain/Translations/en_US/resources.json

@@ -1102,6 +1102,7 @@
     "Composer_CcBcc": "Cc & Bcc",
     "Composer_EnableSmimeSignature": "Enable/disable S/MIME signature",
     "Composer_EnableSmimeEncryption": "Enable/disable S/MIME encryption",
+    "Composer_RequestReadReceipt": "Request read receipt",
     "Composer_LocalDraftSyncInfo": "This draft is local only. Wino failed to send it to your mail server. Click to retry sending it to the server.",
     "Composer_CertificateExpires": "Expires on: ",
     "Composer_SmimeSignature": "S/MIME Signature",
@@ -1168,6 +1169,8 @@
     "Composer_AiTranslateSuccessTitle": "AI translation applied",
     "Composer_AiRewriteSuccessTitle": "AI rewrite applied",
     "Composer_AiErrorTitle": "AI action failed",
+    "MailReceiptStatus_Requested": "Receipt requested",
+    "MailReceiptStatus_Acknowledged": "Read receipt received",
     "Reader_AiAppliedMessage": "The AI result is now shown for this message. Reopen the message to view the original content again.",
     "SettingsAppPreferences_EmailSyncInterval_Title": "Email sync interval",
     "SettingsAppPreferences_EmailSyncInterval_Description": "Automatic email synchronization interval (minutes). This setting will be applied only after restarting Wino Mail.",

Wino.Core.Tests/Helpers/InMemoryDatabaseService.cs

@@ -50,6 +50,7 @@ public class InMemoryDatabaseService : IDatabaseService
         await Connection.CreateTableAsync<CalendarAttachment>();
         await Connection.CreateTableAsync<Reminder>();
         await Connection.CreateTableAsync<MailInvitationCalendarMapping>();
+        await Connection.CreateTableAsync<SentMailReceiptState>();
         await Connection.CreateTableAsync<WinoAccount>();
     }
 

Wino.Core.Tests/Services/MailFetchingTests.cs

@@ -370,6 +370,7 @@ public class MailFetchingTests : IAsyncLifetime
 
         var folderService = new FolderService(db, accountService);
         var contactService = new ContactService(db);
+        var sentMailReceiptService = new SentMailReceiptService(db, folderService, accountService);
 
         return new MailService(
             db,
@@ -378,6 +379,7 @@ public class MailFetchingTests : IAsyncLifetime
             accountService,
             signatureService.Object,
             mimeFileService.Object,
-            preferencesService.Object);
+            preferencesService.Object,
+            sentMailReceiptService);
     }
 }

Wino.Core.Tests/Services/MailThreadingTests.cs

@@ -230,6 +230,7 @@ public class MailThreadingTests : IAsyncLifetime
 
         var folderService = new FolderService(db, accountService);
         var contactService = new ContactService(db);
+        var sentMailReceiptService = new SentMailReceiptService(db, folderService, accountService);
 
         return new MailService(
             db,
@@ -238,6 +239,7 @@ public class MailThreadingTests : IAsyncLifetime
             accountService,
             signatureService.Object,
             mimeFileService.Object,
-            preferencesService.Object);
+            preferencesService.Object,
+            sentMailReceiptService);
     }
 }

Wino.Core.Tests/Services/ReadReceiptTrackingTests.cs

@@ -0,0 +1,151 @@
+using FluentAssertions;
+using MimeKit;
+using Moq;
+using System.IO;
+using System.Text;
+using Wino.Core.Domain;
+using Wino.Core.Domain.Entities.Mail;
+using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Extensions;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Extensions;
+using Wino.Core.Tests.Helpers;
+using Wino.Services;
+using Xunit;
+
+namespace Wino.Core.Tests.Services;
+
+public sealed class ReadReceiptTrackingTests
+{
+    [Fact]
+    public void SetReadReceiptRequest_WhenEnabled_AddsDispositionNotificationHeader()
+    {
+        var mime = new MimeMessage();
+
+        mime.SetReadReceiptRequest("sender@example.com", true);
+
+        mime.HasReadReceiptRequest().Should().BeTrue();
+        mime.Headers[Constants.DispositionNotificationToHeader].Should().Be("sender@example.com");
+    }
+
+    [Fact]
+    public void SetReadReceiptRequest_WhenDisabled_RemovesDispositionNotificationHeader()
+    {
+        var mime = new MimeMessage();
+        mime.Headers.Add(Constants.DispositionNotificationToHeader, "sender@example.com");
+
+        mime.SetReadReceiptRequest("sender@example.com", false);
+
+        mime.HasReadReceiptRequest().Should().BeFalse();
+    }
+
+    [Fact]
+    public void ParseReadReceipt_ExtractsOriginalMessageIdAndAcknowledgedTime()
+    {
+        var mime = new MimeMessage
+        {
+            Date = new DateTimeOffset(2026, 04, 10, 12, 30, 0, TimeSpan.Zero),
+            Body = CreateDispositionNotificationBody("Final-Recipient: rfc822; recipient@example.com\r\nOriginal-Message-ID: <original@example.com>\r\nDisposition: manual-action/MDN-sent-manually; displayed\r\n")
+        };
+
+        var result = mime.ParseReadReceipt();
+
+        result.IsReadReceipt.Should().BeTrue();
+        result.OriginalMessageId.Should().Be("original@example.com");
+        result.AcknowledgedAtUtc.Should().Be(new DateTime(2026, 04, 10, 12, 30, 0, DateTimeKind.Utc));
+    }
+
+    [Fact]
+    public void AsOutlookMessage_WhenMimeRequestsReadReceipt_SetsGraphFlag()
+    {
+        var mime = new MimeMessage
+        {
+            Subject = "Test receipt request",
+            Body = new TextPart("plain") { Text = "Hello" }
+        };
+        mime.MessageId = "test@example.com";
+        mime.From.Add(new MailboxAddress("Sender", "sender@example.com"));
+        mime.To.Add(new MailboxAddress("Recipient", "recipient@example.com"));
+        mime.SetReadReceiptRequest("sender@example.com", true);
+
+        var message = mime.AsOutlookMessage(includeInternetHeaders: false);
+
+        message.IsReadReceiptRequested.Should().BeTrue();
+    }
+
+    [Fact]
+    public async Task ProcessIncomingReceiptAsync_MatchesSentMailByMessageId_AndAcknowledgesState()
+    {
+        var db = new InMemoryDatabaseService();
+        await db.InitializeAsync();
+
+        var account = new MailAccount
+        {
+            Id = Guid.NewGuid(),
+            Address = "sender@example.com",
+            SenderName = "Sender"
+        };
+
+        var sentFolder = new MailItemFolder
+        {
+            Id = Guid.NewGuid(),
+            MailAccountId = account.Id,
+            FolderName = "Sent",
+            SpecialFolderType = SpecialFolderType.Sent
+        };
+
+        var sentMail = new MailCopy
+        {
+            UniqueId = Guid.NewGuid(),
+            Id = "sent-1",
+            FolderId = sentFolder.Id,
+            MessageId = "original@example.com",
+            CreationDate = new DateTime(2026, 04, 10, 10, 0, 0, DateTimeKind.Utc)
+        };
+
+        await db.Connection.InsertAsync(account, typeof(MailAccount));
+        await db.Connection.InsertAsync(sentFolder, typeof(MailItemFolder));
+        await db.Connection.InsertAsync(sentMail, typeof(MailCopy));
+
+        var folderService = new Mock<IFolderService>(MockBehavior.Strict);
+        folderService.Setup(x => x.GetFolderAsync(sentFolder.Id)).ReturnsAsync(sentFolder);
+
+        var accountService = new Mock<IAccountService>(MockBehavior.Strict);
+        accountService.Setup(x => x.GetAccountAsync(account.Id)).ReturnsAsync(account);
+
+        var service = new SentMailReceiptService(db, folderService.Object, accountService.Object);
+
+        var receiptMail = new MailCopy
+        {
+            UniqueId = Guid.NewGuid(),
+            AssignedAccount = account
+        };
+
+        var receiptMime = new MimeMessage
+        {
+            Date = new DateTimeOffset(2026, 04, 10, 13, 15, 0, TimeSpan.Zero),
+            Body = CreateDispositionNotificationBody("Original-Message-ID: <original@example.com>\r\nDisposition: manual-action/MDN-sent-manually; displayed\r\n")
+        };
+
+        await service.ProcessIncomingReceiptAsync(receiptMail, receiptMime);
+
+        var receiptState = await db.Connection.FindAsync<SentMailReceiptState>(sentMail.UniqueId);
+        receiptState.Should().NotBeNull();
+        receiptState!.Status.Should().Be(SentMailReceiptStatus.Acknowledged);
+        receiptState.ReceiptMessageUniqueId.Should().Be(receiptMail.UniqueId);
+        receiptState.MessageId.Should().Be("original@example.com");
+    }
+
+    private static Multipart CreateDispositionNotificationBody(string dispositionText)
+    {
+        var report = new Multipart("report");
+        report.ContentType.Parameters.Add("report-type", "disposition-notification");
+        report.Add(new TextPart("plain") { Text = "Read receipt" });
+        report.Add(new MimePart("message", "disposition-notification")
+        {
+            Content = new MimeContent(new MemoryStream(Encoding.UTF8.GetBytes(dispositionText)))
+        });
+        return report;
+    }
+}

Wino.Core.ViewModels/PersonalizationPageViewModel.cs

@@ -345,6 +345,9 @@ public partial class PersonalizationPageViewModel : CoreBaseViewModel
         public bool ThumbnailUpdatedEvent { get; } = false;
         public bool IsBusy { get; } = false;
         public bool IsThreadExpanded { get; } = false;
+        public bool HasReadReceiptTracking { get; } = false;
+        public bool IsReadReceiptAcknowledged { get; } = false;
+        public string ReadReceiptDisplayText { get; } = string.Empty;
         public AccountContact SenderContact { get; } = null;
         event PropertyChangedEventHandler INotifyPropertyChanged.PropertyChanged
         {

Wino.Core/Extensions/OutlookIntegratorExtensions.cs

@@ -42,6 +42,12 @@ public static class OutlookIntegratorExtensions
     public static bool GetIsFlagged(this Message message)
         => message?.Flag?.FlagStatus != null && message.Flag.FlagStatus == FollowupFlagStatus.Flagged;
 
+    public static bool GetIsReadReceiptRequested(this Message message)
+        => message?.IsReadReceiptRequested.GetValueOrDefault() == true
+           || message?.InternetMessageHeaders?.Any(h =>
+               string.Equals(h.Name, Domain.Constants.DispositionNotificationToHeader, StringComparison.OrdinalIgnoreCase)
+               && !string.IsNullOrWhiteSpace(h.Value)) == true;
+
     public static MailCopy AsMailCopy(this Message outlookMessage)
     {
         bool isDraft = GetIsDraft(outlookMessage);
@@ -53,6 +59,7 @@ public static class OutlookIntegratorExtensions
             IsFocused = GetIsFocused(outlookMessage),
             Importance = !outlookMessage.Importance.HasValue ? MailImportance.Normal : (MailImportance)outlookMessage.Importance.Value,
             IsRead = GetIsRead(outlookMessage),
+            IsReadReceiptRequested = GetIsReadReceiptRequested(outlookMessage),
             IsDraft = isDraft,
             CreationDate = outlookMessage.ReceivedDateTime.GetValueOrDefault().DateTime,
             HasAttachments = outlookMessage.HasAttachments.GetValueOrDefault(),
@@ -156,6 +163,7 @@ public static class OutlookIntegratorExtensions
             BccRecipients = bccAddresses,
             From = fromAddress,
             InternetMessageId = MailHeaderExtensions.ToHeaderMessageId(mime.MessageId),
+            IsReadReceiptRequested = mime.HasReadReceiptRequest(),
             ReplyTo = replyToAddresses,
         };
 

Wino.Core/Synchronizers/GmailSynchronizer.cs

@@ -2100,6 +2100,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             IsDraft = isDraft,
             HasAttachments = gmailMessage.Payload?.Parts?.Any(p => !string.IsNullOrEmpty(p.Filename)) ?? false,
             IsRead = !isUnread,
+            IsReadReceiptRequested = HasReadReceiptRequest(gmailMessage.Payload?.Headers),
             IsFlagged = isFlagged,
             IsFocused = isFocused,
             InReplyTo = MailHeaderExtensions.StripAngleBrackets(gmailMessage.Payload?.Headers?.FirstOrDefault(h => h.Name.Equals("In-Reply-To", StringComparison.OrdinalIgnoreCase))?.Value),
@@ -2148,6 +2149,9 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
         if (string.IsNullOrEmpty(copy.MessageId))
             copy.MessageId = MailHeaderExtensions.NormalizeMessageId(mime.Headers[HeaderId.MessageId]);
 
+        if (!copy.IsReadReceiptRequested)
+            copy.IsReadReceiptRequested = mime.HasReadReceiptRequest();
+
         if (string.IsNullOrEmpty(copy.InReplyTo))
             copy.InReplyTo = MailHeaderExtensions.NormalizeMessageId(mime.InReplyTo);
 
@@ -2231,6 +2235,17 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
         return ("", emailOnly);
     }
 
+    private static bool HasReadReceiptRequest(IList<MessagePartHeader> headers)
+        => headers?.Any(h => h.Name.Equals(Domain.Constants.DispositionNotificationToHeader, StringComparison.OrdinalIgnoreCase)
+                             && !string.IsNullOrWhiteSpace(h.Value)) == true;
+
+    private static bool LooksLikeReadReceipt(IList<MessagePartHeader> headers)
+    {
+        var contentType = headers?.FirstOrDefault(h => h.Name.Equals("Content-Type", StringComparison.OrdinalIgnoreCase))?.Value;
+        return !string.IsNullOrWhiteSpace(contentType)
+               && contentType.Contains("disposition-notification", StringComparison.OrdinalIgnoreCase);
+    }
+
     private static IReadOnlyList<AccountContact> ExtractContactsFromGmailMessage(Message message, MimeMessage mimeMessage)
     {
         var contacts = new Dictionary<string, AccountContact>(StringComparer.OrdinalIgnoreCase);
@@ -2348,7 +2363,9 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
 
         // Initial sync metadata flow does not include MIME, but calendar invitations need MIME
         // for date rendering and invitation-to-calendar mapping.
-        if (mimeMessage == null && baseMailCopy?.ItemType == MailItemType.CalendarInvitation && !string.IsNullOrEmpty(message?.Id))
+        if (mimeMessage == null &&
+            (baseMailCopy?.ItemType == MailItemType.CalendarInvitation || LooksLikeReadReceipt(message?.Payload?.Headers)) &&
+            !string.IsNullOrEmpty(message?.Id))
         {
             try
             {
@@ -2363,7 +2380,7 @@ public class GmailSynchronizer : WinoSynchronizer<IClientServiceRequest, Message
             }
             catch (Exception ex)
             {
-                _logger.Warning(ex, "Failed to fetch raw MIME for calendar invitation {MessageId}", message.Id);
+                _logger.Warning(ex, "Failed to fetch raw MIME for Gmail message {MessageId}", message.Id);
             }
         }
 

Wino.Core/Synchronizers/OutlookSynchronizer.cs

@@ -90,6 +90,7 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
         "Flag",
         "Importance",
         "IsRead",
+        "IsReadReceiptRequested",
         "IsDraft",
         "ReceivedDateTime",
         "HasAttachments",
@@ -401,7 +402,7 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
                         {
                             // For drafts and calendar invitations, download MIME during initial sync like delta sync.
                             var itemType = Account.IsCalendarAccessGranted ? message.GetMailItemType() : MailItemType.Mail;
-                            if (folder.SpecialFolderType == SpecialFolderType.Draft || itemType == MailItemType.CalendarInvitation)
+                            if (ShouldDownloadMimeForMessage(message, folder, itemType))
                             {
                                 var draftPackages = await CreateNewMailPackagesAsync(message, folder, cancellationToken).ConfigureAwait(false);
 
@@ -592,24 +593,47 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
 
                         if (message != null)
                         {
-                            // Create MailCopy from metadata only
-                            var mailCopy = await CreateMailCopyFromMessageAsync(message, folder).ConfigureAwait(false);
+                            var itemType = Account.IsCalendarAccessGranted ? message.GetMailItemType() : MailItemType.Mail;
 
-                            if (mailCopy != null)
+                            if (ShouldDownloadMimeForMessage(message, folder, itemType))
                             {
-                                // Create package without MIME
-                                var contacts = ExtractContactsFromOutlookMessage(message);
-                                var package = new NewMailItemPackage(mailCopy, null, folder.RemoteFolderId, contacts);
-                                bool isInserted = await _outlookChangeProcessor.CreateMailAsync(Account.Id, package).ConfigureAwait(false);
+                                var packages = await CreateNewMailPackagesAsync(message, folder, cancellationToken).ConfigureAwait(false);
 
-                                if (isInserted)
+                                if (packages != null)
                                 {
-                                    downloadedIds.Add(mailCopy.Id);
-                                    _logger.Debug("Downloaded metadata for message {MailId} in folder {FolderName}", messageId, folder.FolderName);
+                                    foreach (var package in packages)
+                                    {
+                                        bool isInserted = await _outlookChangeProcessor.CreateMailAsync(Account.Id, package).ConfigureAwait(false);
+
+                                        if (isInserted)
+                                        {
+                                            downloadedIds.Add(package.Copy.Id);
+                                            _logger.Debug("Downloaded MIME-backed message {MailId} in folder {FolderName}", messageId, folder.FolderName);
+                                        }
+                                    }
                                 }
-                                else
+                            }
+                            else
+                            {
+                                // Create MailCopy from metadata only
+                                var mailCopy = await CreateMailCopyFromMessageAsync(message, folder).ConfigureAwait(false);
+
+                                if (mailCopy != null)
                                 {
-                                    _logger.Warning("Failed to insert mail {MailId} for folder {FolderName}", messageId, folder.FolderName);
+                                    // Create package without MIME
+                                    var contacts = ExtractContactsFromOutlookMessage(message);
+                                    var package = new NewMailItemPackage(mailCopy, null, folder.RemoteFolderId, contacts);
+                                    bool isInserted = await _outlookChangeProcessor.CreateMailAsync(Account.Id, package).ConfigureAwait(false);
+
+                                    if (isInserted)
+                                    {
+                                        downloadedIds.Add(mailCopy.Id);
+                                        _logger.Debug("Downloaded metadata for message {MailId} in folder {FolderName}", messageId, folder.FolderName);
+                                    }
+                                    else
+                                    {
+                                        _logger.Warning("Failed to insert mail {MailId} for folder {FolderName}", messageId, folder.FolderName);
+                                    }
                                 }
                             }
                         }
@@ -685,6 +709,21 @@ public class OutlookSynchronizer : WinoSynchronizer<RequestInformation, Message,
     /// Creates a MailCopy from an Outlook Message with metadata only (centralized method).
     /// This replaces the scattered CreateMinimalMailCopyAsync and AsMailCopy calls.
     /// </summary>
+    private static bool ShouldDownloadMimeForMessage(Message message, MailItemFolder folder, MailItemType itemType)
+        => folder.SpecialFolderType == SpecialFolderType.Draft
+           || itemType == MailItemType.CalendarInvitation
+           || LooksLikeReadReceipt(message);
+
+    private static bool LooksLikeReadReceipt(Message message)
+    {
+        var contentType = message?.InternetMessageHeaders?
+            .FirstOrDefault(h => string.Equals(h.Name, "Content-Type", StringComparison.OrdinalIgnoreCase))
+            ?.Value;
+
+        return !string.IsNullOrWhiteSpace(contentType)
+               && contentType.Contains("disposition-notification", StringComparison.OrdinalIgnoreCase);
+    }
+
     private async Task<MailCopy> CreateMailCopyFromMessageAsync(Message message, MailItemFolder assignedFolder)
     {
         if (message == null) return null;

Wino.Mail.ViewModels/ComposePageViewModel.cs

@@ -123,6 +123,9 @@ public partial class ComposePageViewModel : MailBaseViewModel,
     [ObservableProperty]
     public partial bool IsSmimeEncryptionEnabled { get; set; }
 
+    [ObservableProperty]
+    public partial bool IsReadReceiptRequested { get; set; }
+
     [ObservableProperty]
     public partial X509Certificate2 SelectedSigningCertificate { get; set; }
 
@@ -421,6 +424,7 @@ public partial class ComposePageViewModel : MailBaseViewModel,
         SaveImportance();
         SaveSubject();
         SaveFromAddress();
+        SaveReadReceiptRequest();
         SaveReplyToAddress();
 
         await SaveAttachmentsAsync();
@@ -754,6 +758,7 @@ public partial class ComposePageViewModel : MailBaseViewModel,
                 IsCCBCCVisible = true;
 
             Subject = replyingMime.Subject;
+            IsReadReceiptRequested = replyingMime.HasReadReceiptRequest();
 
             Messenger.Send(new CreateNewComposeMailRequested(renderModel));
         });
@@ -816,6 +821,15 @@ public partial class ComposePageViewModel : MailBaseViewModel,
         }
     }
 
+    private void SaveReadReceiptRequest()
+    {
+        if (CurrentMimeMessage == null)
+            return;
+
+        var receiptAddress = SelectedAlias?.AliasAddress ?? ComposingAccount?.Address ?? string.Empty;
+        CurrentMimeMessage.SetReadReceiptRequest(receiptAddress, IsReadReceiptRequested);
+    }
+
     private void SaveAddressInfo(IEnumerable<AccountContact> addresses, InternetAddressList list)
     {
         list.Clear();

Wino.Mail.ViewModels/Data/AccountContactViewModel.cs

@@ -68,6 +68,9 @@ public partial class AccountContactViewModel : ObservableObject, IMailItemDispla
     public DateTime CreationDate => default;
     public bool IsBusy => false;
     public bool IsThreadExpanded => false;
+    public bool HasReadReceiptTracking => false;
+    public bool IsReadReceiptAcknowledged => false;
+    public string ReadReceiptDisplayText => string.Empty;
     public AccountContact SenderContact => new()
     {
         Address = Address,

Wino.Mail.ViewModels/Data/MailItemViewModel.cs

@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using CommunityToolkit.Mvvm.ComponentModel;
+using Wino.Core.Domain;
 using Wino.Core.Domain.Entities.Mail;
 using Wino.Core.Domain.Entities.Shared;
 using Wino.Core.Domain.Enums;
@@ -105,6 +106,17 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         set => SetProperty(MailCopy.IsDraft, value, MailCopy, (u, n) => u.IsDraft = n);
     }
 
+    public bool HasReadReceiptTracking => MailCopy.IsReadReceiptRequested;
+
+    public bool IsReadReceiptAcknowledged => MailCopy.ReadReceiptStatus == SentMailReceiptStatus.Acknowledged;
+
+    public string ReadReceiptDisplayText => MailCopy.ReadReceiptStatus switch
+    {
+        SentMailReceiptStatus.Acknowledged => Translator.MailReceiptStatus_Acknowledged,
+        SentMailReceiptStatus.Requested => Translator.MailReceiptStatus_Requested,
+        _ => string.Empty
+    };
+
     public string DraftId
     {
         get => MailCopy.DraftId;
@@ -225,6 +237,7 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
             nameof(IsFocused) => MailCopyChangeFlags.IsFocused,
             nameof(IsRead) => MailCopyChangeFlags.IsRead,
             nameof(IsDraft) => MailCopyChangeFlags.IsDraft,
+            nameof(HasReadReceiptTracking) or nameof(IsReadReceiptAcknowledged) or nameof(ReadReceiptDisplayText) => MailCopyChangeFlags.ReadReceiptState,
             nameof(DraftId) => MailCopyChangeFlags.DraftId,
             nameof(Id) => MailCopyChangeFlags.Id,
             nameof(Subject) => MailCopyChangeFlags.Subject,
@@ -287,6 +300,10 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
             changedFlags |= SetIfChanged(MailCopy.AssignedAccount, source.AssignedAccount, value => MailCopy.AssignedAccount = value, MailCopyChangeFlags.AssignedAccount);
             changedFlags |= SetIfChanged(MailCopy.AssignedFolder, source.AssignedFolder, value => MailCopy.AssignedFolder = value, MailCopyChangeFlags.AssignedFolder);
             changedFlags |= SetIfChanged(MailCopy.UniqueId, source.UniqueId, value => MailCopy.UniqueId = value, MailCopyChangeFlags.UniqueId);
+            changedFlags |= SetIfChanged(MailCopy.IsReadReceiptRequested, source.IsReadReceiptRequested, value => MailCopy.IsReadReceiptRequested = value, MailCopyChangeFlags.ReadReceiptState);
+            changedFlags |= SetIfChanged(MailCopy.ReadReceiptStatus, source.ReadReceiptStatus, value => MailCopy.ReadReceiptStatus = value, MailCopyChangeFlags.ReadReceiptState);
+            changedFlags |= SetIfChanged(MailCopy.ReadReceiptAcknowledgedAtUtc, source.ReadReceiptAcknowledgedAtUtc, value => MailCopy.ReadReceiptAcknowledgedAtUtc = value, MailCopyChangeFlags.ReadReceiptState);
+            changedFlags |= SetIfChanged(MailCopy.ReadReceiptMessageUniqueId, source.ReadReceiptMessageUniqueId, value => MailCopy.ReadReceiptMessageUniqueId = value, MailCopyChangeFlags.ReadReceiptState);
         }
 
         changedFlags |= changeHint;
@@ -358,6 +375,13 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         if ((changedFlags & MailCopyChangeFlags.IsDraft) != 0)
             Queue(nameof(IsDraft));
 
+        if ((changedFlags & MailCopyChangeFlags.ReadReceiptState) != 0)
+        {
+            Queue(nameof(HasReadReceiptTracking));
+            Queue(nameof(IsReadReceiptAcknowledged));
+            Queue(nameof(ReadReceiptDisplayText));
+        }
+
         if ((changedFlags & MailCopyChangeFlags.DraftId) != 0)
             Queue(nameof(DraftId));
 

Wino.Mail.ViewModels/Data/ThreadMailItemViewModel.cs

@@ -100,6 +100,12 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     /// </summary>
     public bool IsRead => ThreadEmails.All(e => e.IsRead);
 
+    public bool HasReadReceiptTracking => latestMailViewModel?.HasReadReceiptTracking ?? false;
+
+    public bool IsReadReceiptAcknowledged => latestMailViewModel?.IsReadReceiptAcknowledged ?? false;
+
+    public string ReadReceiptDisplayText => latestMailViewModel?.ReadReceiptDisplayText ?? string.Empty;
+
     /// <summary>
     /// Gets whether any email in this thread is a draft
     /// </summary>
@@ -177,6 +183,9 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     [NotifyPropertyChangedFor(nameof(IsFlagged))]
     [NotifyPropertyChangedFor(nameof(IsFocused))]
     [NotifyPropertyChangedFor(nameof(IsRead))]
+    [NotifyPropertyChangedFor(nameof(HasReadReceiptTracking))]
+    [NotifyPropertyChangedFor(nameof(IsReadReceiptAcknowledged))]
+    [NotifyPropertyChangedFor(nameof(ReadReceiptDisplayText))]
     [NotifyPropertyChangedFor(nameof(IsDraft))]
     [NotifyPropertyChangedFor(nameof(DraftId))]
     [NotifyPropertyChangedFor(nameof(Id))]
@@ -451,6 +460,13 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
         if ((changedFlags & MailCopyChangeFlags.IsRead) != 0 || changedFlags == MailCopyChangeFlags.All)
             Queue(nameof(IsRead));
 
+        if ((changedFlags & MailCopyChangeFlags.ReadReceiptState) != 0 || changedFlags == MailCopyChangeFlags.All)
+        {
+            Queue(nameof(HasReadReceiptTracking));
+            Queue(nameof(IsReadReceiptAcknowledged));
+            Queue(nameof(ReadReceiptDisplayText));
+        }
+
         if ((changedFlags & MailCopyChangeFlags.IsDraft) != 0 || changedFlags == MailCopyChangeFlags.All)
             Queue(nameof(IsDraft));
 

Wino.Mail.ViewModels/MessageListPageViewModel.cs

@@ -164,10 +164,13 @@ public partial class MessageListPageViewModel : MailBaseViewModel
         public Guid? ContactPictureFileId => null;
         public bool ThumbnailUpdatedEvent => false;
         public bool IsThreadExpanded => false;
+        public bool HasReadReceiptTracking => true;
+        public bool IsReadReceiptAcknowledged => false;
+        public string ReadReceiptDisplayText => Translator.MailReceiptStatus_Requested;
         public AccountContact SenderContact => new()
         {
-            Address = "ava@contoso.com",
-            Name = "Ava Brooks"
+            Address = "hi@bkaan.dev",
+            Name = "Burak Kaan Köse"
         };
     }
 }

Wino.Mail.WinUI/Controls/MailItemDisplayInformationControl.xaml

@@ -234,6 +234,15 @@
                                 Orientation="Horizontal"
                                 Spacing="2">
 
+                                <TextBlock
+                                    Margin="0,0,4,0"
+                                    VerticalAlignment="Center"
+                                    FontSize="11"
+                                    Opacity="0.8"
+                                    Text="{x:Bind MailItemInformation.ReadReceiptDisplayText, Mode=OneWay}"
+                                    TextTrimming="CharacterEllipsis"
+                                    Visibility="{x:Bind helpers:XamlHelpers.StringToVisibilityConverter(MailItemInformation.ReadReceiptDisplayText), Mode=OneWay}" />
+
                                 <ContentPresenter
                                     x:Name="HasAttachmentContent"
                                     x:Load="{x:Bind MailItemInformation.HasAttachments, Mode=OneWay}"

Wino.Mail.WinUI/Views/Mail/ComposePage.xaml

@@ -302,6 +302,19 @@
                                     </Viewbox>
                                 </ToggleButton.Content>
                             </ToggleButton>
+                            <ToggleButton
+                                Margin="8,0,0,0"
+                                IsChecked="{x:Bind ViewModel.IsReadReceiptRequested, Mode=TwoWay}"
+                                ToolTipService.ToolTip="{x:Bind domain:Translator.Composer_RequestReadReceipt}">
+                                <ToggleButton.Content>
+                                    <Viewbox
+                                        Width="16"
+                                        Height="16"
+                                        Margin="0,0,4,0">
+                                        <PathIcon Data="M10.75 2.5a6.75 6.75 0 1 0 0 13.5 6.75 6.75 0 0 0 0-13.5ZM2.5 9.25a8.25 8.25 0 1 1 15.036 4.71l2.507 2.507a.75.75 0 1 1-1.06 1.06l-2.507-2.507A8.25 8.25 0 0 1 2.5 9.25Zm8.25-3.5a.75.75 0 0 1 .75.75v2.44l1.78 1.187a.75.75 0 0 1-.832 1.248l-2.114-1.41a.75.75 0 0 1-.334-.624V6.5a.75.75 0 0 1 .75-.75Z" />
+                                    </Viewbox>
+                                </ToggleButton.Content>
+                            </ToggleButton>
                         </StackPanel>
                     </controls1:EditorTabbedCommandBarControl.OptionsCustomContent>
                 </controls1:EditorTabbedCommandBarControl>

Wino.Services/DatabaseService.cs

@@ -68,6 +68,7 @@ public class DatabaseService : IDatabaseService
             Connection.CreateTableAsync<CalendarAttachment>(),
             Connection.CreateTableAsync<Reminder>(),
             Connection.CreateTableAsync<MailInvitationCalendarMapping>(),
+            Connection.CreateTableAsync<SentMailReceiptState>(),
             Connection.CreateTableAsync<WinoAccount>());
 
         await EnsureSchemaUpgradesAsync().ConfigureAwait(false);
@@ -225,5 +226,8 @@ SET {nameof(KeyboardShortcut.Action)} =
         await Connection.ExecuteAsync("CREATE INDEX IF NOT EXISTS IX_MailInvitationCalendarMapping_InvitationUid ON MailInvitationCalendarMapping(InvitationUid)").ConfigureAwait(false);
         await Connection.ExecuteAsync("CREATE INDEX IF NOT EXISTS IX_MailInvitationCalendarMapping_CalendarId ON MailInvitationCalendarMapping(CalendarId)").ConfigureAwait(false);
         await Connection.ExecuteAsync("CREATE INDEX IF NOT EXISTS IX_MailInvitationCalendarMapping_CalendarItemId ON MailInvitationCalendarMapping(CalendarItemId)").ConfigureAwait(false);
+        await Connection.ExecuteAsync("CREATE UNIQUE INDEX IF NOT EXISTS IX_SentMailReceiptState_MailUniqueId ON SentMailReceiptState(MailUniqueId)").ConfigureAwait(false);
+        await Connection.ExecuteAsync("CREATE INDEX IF NOT EXISTS IX_SentMailReceiptState_AccountId_MessageId ON SentMailReceiptState(AccountId, MessageId)").ConfigureAwait(false);
+        await Connection.ExecuteAsync("CREATE INDEX IF NOT EXISTS IX_SentMailReceiptState_Status ON SentMailReceiptState(Status)").ConfigureAwait(false);
     }
 }

Wino.Services/Extensions/MailkitClientExtensions.cs

@@ -121,6 +121,9 @@ public static class MailkitClientExtensions
             MessageId = messageId,
             Subject = subject,
             IsRead = messageSummary.Flags.GetIsRead(),
+            IsReadReceiptRequested = mime?.HasReadReceiptRequest()
+                                     ?? (messageSummary.Headers?.Contains(Constants.DispositionNotificationToHeader) == true
+                                         && !string.IsNullOrWhiteSpace(messageSummary.Headers[Constants.DispositionNotificationToHeader])),
             IsFlagged = messageSummary.Flags.GetIsFlagged(),
             PreviewText = previewText,
             FromAddress = fromAddress,

Wino.Services/MailService.cs

@@ -31,6 +31,7 @@ public class MailService : BaseDatabaseService, IMailService
     private readonly ISignatureService _signatureService;
     private readonly IMimeFileService _mimeFileService;
     private readonly IPreferencesService _preferencesService;
+    private readonly ISentMailReceiptService _sentMailReceiptService;
 
     private readonly ILogger _logger = Log.ForContext<MailService>();
 
@@ -40,7 +41,8 @@ public class MailService : BaseDatabaseService, IMailService
                        IAccountService accountService,
                        ISignatureService signatureService,
                        IMimeFileService mimeFileService,
-                       IPreferencesService preferencesService) : base(databaseService)
+                       IPreferencesService preferencesService,
+                       ISentMailReceiptService sentMailReceiptService) : base(databaseService)
     {
         _folderService = folderService;
         _contactService = contactService;
@@ -48,6 +50,7 @@ public class MailService : BaseDatabaseService, IMailService
         _signatureService = signatureService;
         _mimeFileService = mimeFileService;
         _preferencesService = preferencesService;
+        _sentMailReceiptService = sentMailReceiptService;
     }
 
     public async Task<(MailCopy draftMailCopy, string draftBase64MimeMessage)> CreateDraftAsync(Guid accountId, DraftCreationOptions draftCreationOptions)
@@ -363,6 +366,7 @@ public class MailService : BaseDatabaseService, IMailService
         // 5. Assign all properties synchronously from the pre-loaded in-memory caches - no DB calls here.
         AssignPropertiesFromCaches(mails, folderCache, accountCache, contactCache);
         mails.RemoveAll(m => m.AssignedAccount == null || m.AssignedFolder == null);
+        await _sentMailReceiptService.PopulateReceiptStatesAsync(mails).ConfigureAwait(false);
 
         if (!options.CreateThreads || mails.Count == 0)
             return [.. mails];
@@ -418,6 +422,8 @@ public class MailService : BaseDatabaseService, IMailService
             mails.AddRange(threadMails.Where(m => m.AssignedAccount != null && m.AssignedFolder != null));
         }
 
+        await _sentMailReceiptService.PopulateReceiptStatesAsync(mails).ConfigureAwait(false);
+
         cancellationToken.ThrowIfCancellationRequested();
         return [.. mails];
     }
@@ -568,6 +574,7 @@ public class MailService : BaseDatabaseService, IMailService
         mailCopy.AssignedAccount = account;
         mailCopy.AssignedFolder = folder;
         mailCopy.SenderContact = await GetSenderContactForAccountAsync(account, mailCopy.FromAddress).ConfigureAwait(false);
+        await _sentMailReceiptService.PopulateReceiptStateAsync(mailCopy).ConfigureAwait(false);
     }
 
     public async Task<MailCopy> GetSingleMailItemWithoutFolderAssignmentAsync(string mailCopyId)
@@ -843,6 +850,8 @@ public class MailService : BaseDatabaseService, IMailService
         var insertMailTask = InsertMailAsync(mailCopy);
 
         await Task.WhenAll(mimeSaveTask, insertMailTask).ConfigureAwait(false);
+        await _sentMailReceiptService.TrackSentMailAsync(mailCopy, mimeMessage).ConfigureAwait(false);
+        await _sentMailReceiptService.ProcessIncomingReceiptAsync(mailCopy, mimeMessage).ConfigureAwait(false);
     }
 
     public async Task CreateMailAsyncEx(Guid accountId, NewMailItemPackage package)
@@ -919,6 +928,8 @@ public class MailService : BaseDatabaseService, IMailService
             mailCopy.UniqueId = existingCopyItem.UniqueId;
 
             await UpdateMailAsync(mailCopy).ConfigureAwait(false);
+            await _sentMailReceiptService.TrackSentMailAsync(mailCopy, mimeMessage).ConfigureAwait(false);
+            await _sentMailReceiptService.ProcessIncomingReceiptAsync(mailCopy, mimeMessage).ConfigureAwait(false);
 
             return false;
         }
@@ -933,6 +944,8 @@ public class MailService : BaseDatabaseService, IMailService
             }
 
             await InsertMailAsync(mailCopy).ConfigureAwait(false);
+            await _sentMailReceiptService.TrackSentMailAsync(mailCopy, mimeMessage).ConfigureAwait(false);
+            await _sentMailReceiptService.ProcessIncomingReceiptAsync(mailCopy, mimeMessage).ConfigureAwait(false);
 
             return true;
         }

Wino.Services/SentMailReceiptService.cs

@@ -0,0 +1,161 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Threading.Tasks;
+using Wino.Core.Domain.Entities.Mail;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Extensions;
+using Wino.Core.Domain.Interfaces;
+using Wino.Messaging.UI;
+
+namespace Wino.Services;
+
+public class SentMailReceiptService(
+    IDatabaseService databaseService,
+    IFolderService folderService,
+    IAccountService accountService) : BaseDatabaseService(databaseService), ISentMailReceiptService
+{
+    public async Task PopulateReceiptStateAsync(MailCopy mailCopy)
+    {
+        if (mailCopy == null)
+            return;
+
+        var state = await Connection.FindAsync<SentMailReceiptState>(mailCopy.UniqueId).ConfigureAwait(false);
+        ApplyState(mailCopy, state);
+    }
+
+    public async Task PopulateReceiptStatesAsync(IReadOnlyCollection<MailCopy> mailCopies)
+    {
+        if (mailCopies == null || mailCopies.Count == 0)
+            return;
+
+        var uniqueIds = mailCopies
+            .Select(m => m.UniqueId)
+            .Where(id => id != Guid.Empty)
+            .Distinct()
+            .ToList();
+
+        if (uniqueIds.Count == 0)
+            return;
+
+        var placeholders = string.Join(",", uniqueIds.Select(_ => "?"));
+        var states = await Connection.QueryAsync<SentMailReceiptState>(
+            $"SELECT * FROM {nameof(SentMailReceiptState)} WHERE {nameof(SentMailReceiptState.MailUniqueId)} IN ({placeholders})",
+            uniqueIds.Cast<object>().ToArray()).ConfigureAwait(false);
+
+        var stateLookup = states.ToDictionary(s => s.MailUniqueId);
+
+        foreach (var mailCopy in mailCopies)
+        {
+            stateLookup.TryGetValue(mailCopy.UniqueId, out var state);
+            ApplyState(mailCopy, state);
+        }
+    }
+
+    public async Task TrackSentMailAsync(MailCopy mailCopy, MimeKit.MimeMessage mimeMessage = null)
+    {
+        if (mailCopy?.AssignedFolder == null || mailCopy.AssignedAccount == null)
+            return;
+
+        if (mailCopy.AssignedFolder.SpecialFolderType != SpecialFolderType.Sent)
+            return;
+
+        var isRequested = mailCopy.IsReadReceiptRequested || mimeMessage.HasReadReceiptRequest();
+        if (!isRequested || string.IsNullOrWhiteSpace(mailCopy.MessageId))
+            return;
+
+        var existing = await Connection.FindAsync<SentMailReceiptState>(mailCopy.UniqueId).ConfigureAwait(false);
+
+        if (existing == null)
+        {
+            existing = new SentMailReceiptState
+            {
+                MailUniqueId = mailCopy.UniqueId,
+                AccountId = mailCopy.AssignedAccount.Id,
+                MessageId = MailHeaderExtensions.NormalizeMessageId(mailCopy.MessageId),
+                IsReceiptRequested = true,
+                RequestedAtUtc = mailCopy.CreationDate == default ? DateTime.UtcNow : mailCopy.CreationDate,
+                Status = SentMailReceiptStatus.Requested
+            };
+
+            await Connection.InsertAsync(existing, typeof(SentMailReceiptState)).ConfigureAwait(false);
+        }
+        else
+        {
+            existing.AccountId = mailCopy.AssignedAccount.Id;
+            existing.MessageId = MailHeaderExtensions.NormalizeMessageId(mailCopy.MessageId);
+            existing.IsReceiptRequested = true;
+            if (existing.Status == SentMailReceiptStatus.None)
+                existing.Status = SentMailReceiptStatus.Requested;
+
+            await Connection.UpdateAsync(existing, typeof(SentMailReceiptState)).ConfigureAwait(false);
+        }
+
+        ApplyState(mailCopy, existing);
+        ReportUIChange(new MailUpdatedMessage(mailCopy, EntityUpdateSource.Server, MailCopyChangeFlags.ReadReceiptState));
+    }
+
+    public async Task ProcessIncomingReceiptAsync(MailCopy receiptMail, MimeKit.MimeMessage mimeMessage)
+    {
+        if (receiptMail?.AssignedAccount == null || mimeMessage == null)
+            return;
+
+        var parsedReceipt = mimeMessage.ParseReadReceipt();
+        if (!parsedReceipt.IsReadReceipt || string.IsNullOrWhiteSpace(parsedReceipt.OriginalMessageId))
+            return;
+
+        var targetMail = await Connection.FindWithQueryAsync<MailCopy>(
+            "SELECT MailCopy.* FROM MailCopy " +
+            "INNER JOIN MailItemFolder ON MailCopy.FolderId = MailItemFolder.Id " +
+            "WHERE MailItemFolder.MailAccountId = ? AND MailCopy.MessageId = ? AND MailItemFolder.SpecialFolderType = ? " +
+            "ORDER BY MailCopy.CreationDate DESC LIMIT 1",
+            receiptMail.AssignedAccount.Id,
+            parsedReceipt.OriginalMessageId,
+            SpecialFolderType.Sent).ConfigureAwait(false);
+
+        if (targetMail == null)
+            return;
+
+        var state = await Connection.FindAsync<SentMailReceiptState>(targetMail.UniqueId).ConfigureAwait(false)
+            ?? new SentMailReceiptState
+            {
+                MailUniqueId = targetMail.UniqueId,
+                AccountId = receiptMail.AssignedAccount.Id,
+                MessageId = parsedReceipt.OriginalMessageId,
+                RequestedAtUtc = targetMail.CreationDate == default ? DateTime.UtcNow : targetMail.CreationDate,
+                IsReceiptRequested = true,
+                Status = SentMailReceiptStatus.Requested
+            };
+
+        state.AccountId = receiptMail.AssignedAccount.Id;
+        state.MessageId = parsedReceipt.OriginalMessageId;
+        state.IsReceiptRequested = true;
+        state.Status = SentMailReceiptStatus.Acknowledged;
+        state.AcknowledgedAtUtc = parsedReceipt.AcknowledgedAtUtc ?? DateTime.UtcNow;
+        state.ReceiptMessageUniqueId = receiptMail.UniqueId;
+
+        if (await Connection.FindAsync<SentMailReceiptState>(state.MailUniqueId).ConfigureAwait(false) == null)
+            await Connection.InsertAsync(state, typeof(SentMailReceiptState)).ConfigureAwait(false);
+        else
+            await Connection.UpdateAsync(state, typeof(SentMailReceiptState)).ConfigureAwait(false);
+
+        var folder = await folderService.GetFolderAsync(targetMail.FolderId).ConfigureAwait(false);
+        if (folder == null)
+            return;
+
+        var account = await accountService.GetAccountAsync(folder.MailAccountId).ConfigureAwait(false);
+        targetMail.AssignedFolder = folder;
+        targetMail.AssignedAccount = account;
+        ApplyState(targetMail, state);
+
+        ReportUIChange(new MailUpdatedMessage(targetMail, EntityUpdateSource.Server, MailCopyChangeFlags.ReadReceiptState));
+    }
+
+    private static void ApplyState(MailCopy mailCopy, SentMailReceiptState state)
+    {
+        mailCopy.IsReadReceiptRequested = state?.IsReceiptRequested ?? false;
+        mailCopy.ReadReceiptStatus = state?.Status ?? SentMailReceiptStatus.None;
+        mailCopy.ReadReceiptAcknowledgedAtUtc = state?.AcknowledgedAtUtc;
+        mailCopy.ReadReceiptMessageUniqueId = state?.ReceiptMessageUniqueId;
+    }
+}

Wino.Services/ServicesContainerSetup.cs

@@ -19,6 +19,7 @@ public static class ServicesContainerSetup
 
         services.AddTransient<ICalendarService, CalendarService>();
         services.AddTransient<IMailService, MailService>();
+        services.AddTransient<ISentMailReceiptService, SentMailReceiptService>();
         services.AddTransient<IFolderService, FolderService>();
         services.AddTransient<IAccountService, AccountService>();
         services.AddTransient<IContactService, ContactService>();