Fixed iCloud/Yahoo special providers and implemented more calendar metadata to support calendar colors in CalDav synchronizer.

Wino.Authentication/OutlookAuthenticator.cs

@@ -106,10 +106,6 @@ public class OutlookAuthenticator : BaseAuthenticator, IOutlookAuthenticator
 
             return await GenerateTokenInformationAsync(account);
         }
-        catch (Exception)
-        {
-            throw;
-        }
     }
 
     public async Task<TokenInformationEx> GenerateTokenInformationAsync(MailAccount account)
@@ -128,14 +124,8 @@ public class OutlookAuthenticator : BaseAuthenticator, IOutlookAuthenticator
                 .AcquireTokenInteractive(GetScope(account))
                 .ExecuteAsync();
 
-            // If the account is null, it means it's the initial creation of it.
+            // Microsoft 365 work/school tenants can use a sign-in UPN that differs from
-            // If not, make sure the authenticated user address matches the username.
+            // the mailbox primary SMTP address, so interactive reauth must not reject them.
-            // When people refresh their token, accounts must match.
-
-            if (account?.Address != null && !account.Address.Equals(authResult.Account.Username, StringComparison.OrdinalIgnoreCase))
-            {
-                throw new AuthenticationException("Authenticated address does not match with your account address. If you are signing with a Office365, it is not officially supported yet.");
-            }
 
             return new TokenInformationEx(authResult.AccessToken, authResult.Account.Username);
         }

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

@@ -92,6 +92,11 @@ public class MailCopy
     /// </summary>
     public bool IsFlagged { get; set; }
 
+    /// <summary>
+    /// Whether this mail should stay pinned to the top locally.
+    /// </summary>
+    public bool IsPinned { get; set; }
+
     /// <summary>
     /// To support Outlook.
     /// Gmail doesn't use it.
@@ -167,6 +172,9 @@ public class MailCopy
     [Ignore]
     public Guid? ReadReceiptMessageUniqueId { get; set; }
 
+    [Ignore]
+    public List<MailCategory> Categories { get; set; } = [];
+
     public IEnumerable<Guid> GetContainingIds() => [UniqueId];
     public override string ToString() => $"{Subject} <-> {Id}";
 }

Wino.Core.Domain/Enums/MailCopyChangeFlags.cs

@@ -20,17 +20,19 @@ public enum MailCopyChangeFlags
     Importance = 1 << 11,
     IsRead = 1 << 12,
     IsFlagged = 1 << 13,
-    IsFocused = 1 << 14,
+    IsPinned = 1 << 14,
-    HasAttachments = 1 << 15,
+    IsFocused = 1 << 15,
-    ItemType = 1 << 16,
+    HasAttachments = 1 << 16,
-    DraftId = 1 << 17,
+    ItemType = 1 << 17,
-    IsDraft = 1 << 18,
+    DraftId = 1 << 18,
-    FileId = 1 << 19,
+    IsDraft = 1 << 19,
-    AssignedFolder = 1 << 20,
+    FileId = 1 << 20,
-    AssignedAccount = 1 << 21,
+    AssignedFolder = 1 << 21,
-    SenderContact = 1 << 22,
+    AssignedAccount = 1 << 22,
-    UniqueId = 1 << 23,
+    SenderContact = 1 << 23,
-    ReadReceiptState = 1 << 24,
+    UniqueId = 1 << 24,
+    ReadReceiptState = 1 << 25,
+    Categories = 1 << 26,
     All = Id |
           FolderId |
           ThreadId |
@@ -45,6 +47,7 @@ public enum MailCopyChangeFlags
           Importance |
           IsRead |
           IsFlagged |
+          IsPinned |
           IsFocused |
           HasAttachments |
           ItemType |
@@ -55,5 +58,6 @@ public enum MailCopyChangeFlags
           AssignedAccount |
           SenderContact |
           UniqueId |
-          ReadReceiptState
+          ReadReceiptState |
+          Categories
 }

Wino.Core.Domain/Interfaces/IMailCategoryService.cs

@@ -23,6 +23,7 @@ public interface IMailCategoryService
     Task AssignCategoryAsync(Guid categoryId, IEnumerable<Guid> mailCopyUniqueIds);
     Task UnassignCategoryAsync(Guid categoryId, IEnumerable<Guid> mailCopyUniqueIds);
     Task<List<MailCategory>> GetCategoriesForMailAsync(Guid accountId, IEnumerable<Guid> mailCopyUniqueIds);
+    Task<IReadOnlyDictionary<Guid, IReadOnlyList<MailCategory>>> GetCategoriesByMailAsync(Guid accountId, IEnumerable<Guid> mailCopyUniqueIds);
     Task<List<Guid>> GetAssignedCategoryIdsForAllAsync(IEnumerable<Guid> mailCopyUniqueIds);
     Task<List<string>> GetCategoryNamesForMailAsync(Guid mailCopyUniqueId);
     Task<List<MailCopy>> GetMailCopiesForCategoryAsync(Guid categoryId);

Wino.Core.Domain/Interfaces/IMailItemDisplayInformation.cs

@@ -1,5 +1,7 @@
 using System;
+using System.Collections.Generic;
 using System.ComponentModel;
+using Wino.Core.Domain.Entities.Mail;
 using Wino.Core.Domain.Entities.Shared;
 
 namespace Wino.Core.Domain.Interfaces;
@@ -27,4 +29,6 @@ public interface IMailItemDisplayInformation : INotifyPropertyChanged
     bool HasReadReceiptTracking { get; }
     bool IsReadReceiptAcknowledged { get; }
     string ReadReceiptDisplayText { get; }
+    IReadOnlyList<MailCategory> Categories { get; }
+    bool HasCategories { get; }
 }

Wino.Core.Domain/Interfaces/IMailListItemSorting.cs

@@ -6,4 +6,5 @@ public interface IMailListItemSorting
 {
     DateTime SortingDate { get; }
     string SortingName { get; }
+    bool IsPinned { get; }
 }

Wino.Core.Domain/Interfaces/IMailService.cs

@@ -26,6 +26,7 @@ public interface IMailService
     /// </summary>
     Task<List<MailCopy>> GetMailItemsAsync(IEnumerable<string> mailCopyIds);
     Task<List<MailCopy>> FetchMailsAsync(MailListInitializationOptions options, CancellationToken cancellationToken = default);
+    Task<List<MailCopy>> FetchPinnedMailsAsync(MailListInitializationOptions options, CancellationToken cancellationToken = default);
 
     /// <summary>
     /// Deletes all mail copies for all folders.
@@ -36,6 +37,7 @@ public interface IMailService
 
     Task ChangeReadStatusAsync(string mailCopyId, bool isRead);
     Task ChangeFlagStatusAsync(string mailCopyId, bool isFlagged);
+    Task ChangePinnedStatusAsync(IEnumerable<Guid> uniqueMailIds, bool isPinned);
     Task ApplyMailStateUpdatesAsync(IEnumerable<MailCopyStateUpdate> updates);
 
     Task CreateAssignmentAsync(Guid accountId, string mailCopyId, string remoteFolderId);

Wino.Core.Domain/Models/Calendar/CalDavCalendar.cs

@@ -1,10 +1,19 @@
+using Wino.Core.Domain.Enums;
+
 namespace Wino.Core.Domain.Models.Calendar;
 
 public sealed class CalDavCalendar
 {
     public string RemoteCalendarId { get; init; } = string.Empty;
     public string Name { get; init; } = string.Empty;
+    public string Description { get; init; } = string.Empty;
     public string CTag { get; init; } = string.Empty;
     public string SyncToken { get; init; } = string.Empty;
+    public string TimeZone { get; init; } = string.Empty;
+    public string BackgroundColorHex { get; init; } = string.Empty;
+    public bool IsReadOnly { get; init; }
+    public bool SupportsEvents { get; init; } = true;
+    public CalendarItemShowAs DefaultShowAs { get; init; } = CalendarItemShowAs.Busy;
+    public double? Order { get; init; }
 }
 

Wino.Core.Domain/Models/Comparers/ListItemComparer.cs

@@ -1,7 +1,8 @@
-using System;
+using System;
 using System.Collections.Generic;
 using Wino.Core.Domain.Entities.Mail;
 using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.MailItem;
 
 public class ListItemComparer : IComparer<object>
 {
@@ -9,14 +10,48 @@ public class ListItemComparer : IComparer<object>
 
     public int Compare(object x, object y)
     {
+        if (x is MailListGroupKey xGroupKey && y is MailListGroupKey yGroupKey)
+        {
+            if (xGroupKey.IsPinned != yGroupKey.IsPinned)
+                return yGroupKey.IsPinned.CompareTo(xGroupKey.IsPinned);
+
+            if (xGroupKey.IsPinned && yGroupKey.IsPinned)
+                return 0;
+
+            return CompareSortValues(xGroupKey.Value, yGroupKey.Value);
+        }
+
         if (x is IMailListItemSorting xSorting && y is IMailListItemSorting ySorting)
-            return SortByName ? string.Compare(xSorting.SortingName, ySorting.SortingName, StringComparison.OrdinalIgnoreCase) : DateTime.Compare(ySorting.SortingDate, xSorting.SortingDate);
+        {
-        else if (x is MailCopy xMail && y is MailCopy yMail)
+            if (xSorting.IsPinned != ySorting.IsPinned)
-            return SortByName ? string.Compare(xMail.FromName, yMail.FromName, StringComparison.OrdinalIgnoreCase) : DateTime.Compare(yMail.CreationDate, xMail.CreationDate);
+                return ySorting.IsPinned.CompareTo(xSorting.IsPinned);
-        else if (x is DateTime dateX && y is DateTime dateY)
+
+            return SortByName
+                ? string.Compare(xSorting.SortingName, ySorting.SortingName, StringComparison.OrdinalIgnoreCase)
+                : DateTime.Compare(ySorting.SortingDate, xSorting.SortingDate);
+        }
+
+        if (x is MailCopy xMail && y is MailCopy yMail)
+        {
+            if (xMail.IsPinned != yMail.IsPinned)
+                return yMail.IsPinned.CompareTo(xMail.IsPinned);
+
+            return SortByName
+                ? string.Compare(xMail.FromName, yMail.FromName, StringComparison.OrdinalIgnoreCase)
+                : DateTime.Compare(yMail.CreationDate, xMail.CreationDate);
+        }
+
+        return CompareSortValues(x, y);
+    }
+
+    private static int CompareSortValues(object x, object y)
+    {
+        if (x is DateTime dateX && y is DateTime dateY)
             return DateTime.Compare(dateY, dateX);
-        else if (x is string stringX && y is string stringY)
+
+        if (x is string stringX && y is string stringY)
             return stringY.CompareTo(stringX);
+
         return 0;
     }
 }

Wino.Core.Domain/Models/MailItem/HtmlPreviewVisitor.cs

@@ -15,7 +15,7 @@ public class HtmlPreviewVisitor : MimeVisitor
 {
     private static readonly HashSet<string> BlockedTags = new(StringComparer.OrdinalIgnoreCase)
     {
-        "script", "iframe", "frame", "frameset", "object", "embed", "applet", "base", "meta", "form"
+        "script", "iframe", "frame", "frameset", "object", "embed", "applet", "base", "meta", "form", "link"
     };
 
     private static readonly HashSet<string> AllowedDataImageMimeTypes = new(StringComparer.OrdinalIgnoreCase)

Wino.Core.Domain/Models/MailItem/MailListGroupKey.cs

@@ -0,0 +1,6 @@
+namespace Wino.Core.Domain.Models.MailItem;
+
+public sealed record MailListGroupKey(bool IsPinned, object Value)
+{
+    public static MailListGroupKey Pinned { get; } = new(true, null);
+}

Wino.Core.Tests/Models/HtmlPreviewVisitorTests.cs

@@ -15,6 +15,7 @@ public class HtmlPreviewVisitorTests
             <html>
                 <body onload="alert('x')">
                     <h1 onclick="evil()">hello</h1>
+                    <link rel="stylesheet" href="https://tracker.example/mail.css" />
                     <script>alert('xss')</script>
                     <iframe src="https://malicious.example"></iframe>
                     <object data="https://malicious.example/file.swf"></object>
@@ -34,6 +35,7 @@ public class HtmlPreviewVisitorTests
 
         // Assert
         output.Should().NotContain("<script", "script tags must be blocked in rendered html");
+        output.Should().NotContain("<link", "external stylesheet tags must be blocked in rendered html");
         output.Should().NotContain("<iframe", "iframe tags must be blocked in rendered html");
         output.Should().NotContain("<object", "object tags must be blocked in rendered html");
         output.Should().NotContain("onload=", "event handler attributes must be stripped");

Wino.Core.Tests/Services/HtmlAgilityPackExtensionsTests.cs

@@ -0,0 +1,53 @@
+using FluentAssertions;
+using HtmlAgilityPack;
+using Wino.Services.Extensions;
+using Xunit;
+
+namespace Wino.Core.Tests.Services;
+
+public class HtmlAgilityPackExtensionsTests
+{
+    [Fact]
+    public void ClearImages_Should_Block_Remote_Image_References_But_Keep_Embedded_Ones()
+    {
+        // Arrange
+        var document = new HtmlDocument();
+        document.LoadHtml("""
+            <html>
+                <head>
+                    <style>
+                        .hero { background-image: url('https://tracker.example/bg.png'); color: red; }
+                    </style>
+                </head>
+                <body background="https://tracker.example/body.png">
+                    <img id="remote" src="https://tracker.example/pixel.png" />
+                    <img id="embedded" src="data:image/png;base64,AAAA" />
+                    <img id="responsive" srcset="https://tracker.example/1x.png 1x, data:image/png;base64,BBBB 2x" />
+                    <div id="inline-style" style="background-image:url('https://tracker.example/inline.png');color:blue;">hello</div>
+                    <v:fill id="vml" src="https://tracker.example/vml.png"></v:fill>
+                    <svg>
+                        <image id="svg-remote" href="https://tracker.example/vector.svg"></image>
+                        <use id="svg-local" href="#icon"></use>
+                    </svg>
+                </body>
+            </html>
+            """);
+
+        // Act
+        document.ClearImages();
+        var output = document.DocumentNode.OuterHtml;
+
+        // Assert
+        output.Should().Contain("id=\"embedded\" src=\"data:image/png;base64,AAAA\"", "embedded inline images should still render");
+        output.Should().NotContain("id=\"remote\" src=", "remote img sources should be removed");
+        output.Should().NotContain("background=\"https://tracker.example/body.png\"", "background attributes can be used as trackers");
+        output.Should().NotContain("srcset=", "responsive image candidates should be removed because they may fetch remote trackers");
+        output.Should().NotContain("https://tracker.example/inline.png", "inline CSS should not be allowed to fetch remote images");
+        output.Should().Contain("color:blue", "non-image inline styling should be preserved");
+        output.Should().NotContain("https://tracker.example/bg.png", "style blocks should not be allowed to fetch remote images");
+        output.Should().Contain("color: red", "safe CSS declarations should remain");
+        output.Should().NotContain("id=\"vml\" src=", "VML image references should be removed");
+        output.Should().NotContain("id=\"svg-remote\" href=", "SVG image references should not fetch remote content");
+        output.Should().Contain("id=\"svg-local\" href=\"#icon\"", "local fragment references should remain");
+    }
+}

Wino.Core.Tests/Services/MailFetchingTests.cs

@@ -259,6 +259,26 @@ public class MailFetchingTests : IAsyncLifetime
         result.Single().FolderId.Should().Be(_inboxFolder.Id, "a copy from the actively searched folder should win over newer non-searched copies");
     }
 
+    [Fact]
+    public async Task FetchPinnedMailsAsync_ReturnsPinnedMailsOutsideRegularPage()
+    {
+        var oldPinned = BuildMail(_inboxFolder.Id, DateTime.UtcNow.AddDays(-5));
+        oldPinned.IsPinned = true;
+
+        var recentMails = Enumerable.Range(0, 120)
+            .Select(i => BuildMail(_inboxFolder.Id, DateTime.UtcNow.AddMinutes(-i)))
+            .ToList();
+
+        await _databaseService.Connection.InsertAsync(oldPinned, typeof(MailCopy));
+        await _databaseService.Connection.InsertAllAsync(recentMails, typeof(MailCopy));
+
+        var options = BuildOptions([_inboxFolder], createThreads: false, take: 20);
+
+        var result = await _mailService.FetchPinnedMailsAsync(options);
+
+        result.Should().ContainSingle(mail => mail.UniqueId == oldPinned.UniqueId);
+    }
+
     [Fact]
     public async Task CreateAssignmentAsync_ExistingAssignment_IsIgnored()
     {
@@ -297,6 +317,27 @@ public class MailFetchingTests : IAsyncLifetime
         insertedCopies.Select(mail => mail.FolderId).Should().BeEquivalentTo([_inboxFolder.Id, archiveFolder.Id]);
     }
 
+    [Fact]
+    public async Task UpdateMailAsync_PreservesLocalPinnedState()
+    {
+        var existingMail = BuildMail(_inboxFolder.Id, DateTime.UtcNow.AddHours(-1));
+        existingMail.IsPinned = true;
+
+        await _databaseService.Connection.InsertAsync(existingMail, typeof(MailCopy));
+
+        var refreshedMail = BuildMail(_inboxFolder.Id, DateTime.UtcNow, id: existingMail.Id);
+        refreshedMail.UniqueId = existingMail.UniqueId;
+        refreshedMail.FileId = existingMail.FileId;
+        refreshedMail.Subject = "Updated subject";
+
+        await _mailService.UpdateMailAsync(refreshedMail);
+
+        var storedMail = await _databaseService.Connection.FindAsync<MailCopy>(existingMail.UniqueId);
+        storedMail.Should().NotBeNull();
+        storedMail!.IsPinned.Should().BeTrue();
+        storedMail.Subject.Should().Be("Updated subject");
+    }
+
     // ── Performance: 1 000 mails / ~70 threads ─────────────────────────────────
 
     /// <summary>

Wino.Core.Tests/Services/MailThreadingTests.cs

@@ -327,6 +327,94 @@ public class MailThreadingTests : IAsyncLifetime
         }
     }
 
+    [Fact]
+    public async Task ChangePinnedStatusAsync_SendsHydratedBulkMailUpdatedMessage()
+    {
+        var mail = new MailCopy
+        {
+            UniqueId = Guid.NewGuid(),
+            Id = Guid.NewGuid().ToString(),
+            FolderId = _draftFolder.Id,
+            IsPinned = false,
+            Subject = "Pinned draft"
+        };
+
+        await _databaseService.Connection.InsertAsync(mail, typeof(MailCopy));
+
+        var recipient = new MailUpdateRecipient();
+        WeakReferenceMessenger.Default.Register<MailUpdatedMessage>(recipient);
+        WeakReferenceMessenger.Default.Register<BulkMailUpdatedMessage>(recipient);
+
+        try
+        {
+            await _mailService.ChangePinnedStatusAsync([mail.UniqueId], true);
+
+            recipient.SingleUpdates.Should().BeEmpty();
+            recipient.BulkUpdates.Should().ContainSingle();
+            recipient.BulkUpdates[0].ChangedProperties.Should().Be(MailCopyChangeFlags.IsPinned);
+            recipient.BulkUpdates[0].UpdatedMails.Should().ContainSingle();
+
+            var updatedMail = recipient.BulkUpdates[0].UpdatedMails[0];
+            updatedMail.IsPinned.Should().BeTrue();
+            updatedMail.AssignedFolder.Should().NotBeNull();
+            updatedMail.AssignedFolder!.Id.Should().Be(_draftFolder.Id);
+            updatedMail.AssignedAccount.Should().NotBeNull();
+            updatedMail.AssignedAccount!.Id.Should().Be(_account.Id);
+        }
+        finally
+        {
+            WeakReferenceMessenger.Default.Unregister<MailUpdatedMessage>(recipient);
+            WeakReferenceMessenger.Default.Unregister<BulkMailUpdatedMessage>(recipient);
+        }
+    }
+
+    [Fact]
+    public async Task CreateAssignmentAsync_SendsHydratedMailAddedMessage()
+    {
+        var archiveFolder = new MailItemFolder
+        {
+            Id = Guid.NewGuid(),
+            MailAccountId = _account.Id,
+            FolderName = "Archive",
+            RemoteFolderId = "archive",
+            SpecialFolderType = SpecialFolderType.Archive,
+            IsSystemFolder = true,
+            IsSynchronizationEnabled = true
+        };
+
+        var mail = new MailCopy
+        {
+            UniqueId = Guid.NewGuid(),
+            Id = "assignment-mail",
+            FolderId = _draftFolder.Id,
+            Subject = "Assigned copy"
+        };
+
+        await _databaseService.Connection.InsertAsync(archiveFolder, typeof(MailItemFolder));
+        await _databaseService.Connection.InsertAsync(mail, typeof(MailCopy));
+
+        var recipient = new MailAddRecipient();
+        WeakReferenceMessenger.Default.Register<MailAddedMessage>(recipient);
+
+        try
+        {
+            await _mailService.CreateAssignmentAsync(_account.Id, mail.Id, archiveFolder.RemoteFolderId);
+
+            recipient.Added.Should().ContainSingle();
+
+            var addedMail = recipient.Added[0].AddedMail;
+            addedMail.UniqueId.Should().NotBe(mail.UniqueId);
+            addedMail.AssignedFolder.Should().NotBeNull();
+            addedMail.AssignedFolder!.Id.Should().Be(archiveFolder.Id);
+            addedMail.AssignedAccount.Should().NotBeNull();
+            addedMail.AssignedAccount!.Id.Should().Be(_account.Id);
+        }
+        finally
+        {
+            WeakReferenceMessenger.Default.Unregister<MailAddedMessage>(recipient);
+        }
+    }
+
     private static MimeMessage CreateReferencedMimeMessage(string subject, string? messageId = null)
     {
         var message = new MimeMessage();
@@ -350,6 +438,13 @@ public class MailThreadingTests : IAsyncLifetime
         public void Receive(BulkMailUpdatedMessage message) => BulkUpdates.Add(message);
     }
 
+    internal sealed class MailAddRecipient : IRecipient<MailAddedMessage>
+    {
+        public List<MailAddedMessage> Added { get; } = [];
+
+        public void Receive(MailAddedMessage message) => Added.Add(message);
+    }
+
     internal sealed class MailReadStatusRecipient : IRecipient<MailReadStatusChanged>, IRecipient<BulkMailReadStatusChanged>
     {
         public List<MailReadStatusChanged> SingleUpdates { get; } = [];

Wino.Core.Tests/Services/SpecialImapProviderConfigResolverTests.cs

@@ -0,0 +1,41 @@
+using FluentAssertions;
+using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Models.Accounts;
+using Wino.Services;
+using Xunit;
+
+namespace Wino.Core.Tests.Services;
+
+public class SpecialImapProviderConfigResolverTests
+{
+    [Fact]
+    public void GetServerInformation_ICloud_UsesMailboxLocalPartForIncomingAndOutgoingUsernames()
+    {
+        var sut = new SpecialImapProviderConfigResolver();
+        var account = new MailAccount
+        {
+            Id = Guid.NewGuid(),
+            Address = "tester@icloud.com"
+        };
+        var dialogResult = new AccountCreationDialogResult(
+            MailProviderType.IMAP4,
+            "iCloud",
+            new SpecialImapProviderDetails(
+                "tester@icloud.com",
+                "app-password",
+                "Tester",
+                SpecialImapProvider.iCloud,
+                ImapCalendarSupportMode.CalDav),
+            "#0078D4",
+            InitialSynchronizationRange.SixMonths,
+            true,
+            true);
+
+        var serverInformation = sut.GetServerInformation(account, dialogResult);
+
+        serverInformation.IncomingServerUsername.Should().Be("tester");
+        serverInformation.OutgoingServerUsername.Should().Be("tester");
+        serverInformation.CalDavUsername.Should().Be("tester@icloud.com");
+    }
+}

Wino.Core.Tests/Synchronizers/CalDavCalendarMetadataTests.cs

@@ -0,0 +1,262 @@
+using System.Reflection;
+using System.IO;
+using System.Xml.Linq;
+using FluentAssertions;
+using Moq;
+using Wino.Core.Domain.Entities.Calendar;
+using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Calendar;
+using Wino.Core.Integration.Processors;
+using Wino.Core.Misc;
+using Wino.Core.Synchronizers.ImapSync;
+using Wino.Core.Synchronizers.Mail;
+using Wino.Services;
+using Xunit;
+
+namespace Wino.Core.Tests.Synchronizers;
+
+public class CalDavCalendarMetadataTests
+{
+    [Fact]
+    public void ParseCalendarCollection_MapsCollectionMetadataAndSkipsNonEventCalendars()
+    {
+        var xml = XDocument.Parse(
+            """
+            <D:multistatus xmlns:D="DAV:" xmlns:C="urn:ietf:params:xml:ns:caldav" xmlns:CS="http://calendarserver.org/ns/" xmlns:ICAL="http://apple.com/ns/ical/">
+              <D:response>
+                <D:href>/calendars/work/</D:href>
+                <D:propstat>
+                  <D:status>HTTP/1.1 200 OK</D:status>
+                  <D:prop>
+                    <D:resourcetype>
+                      <D:collection />
+                      <C:calendar />
+                    </D:resourcetype>
+                    <D:displayname>Work</D:displayname>
+                    <C:calendar-description>Team calendar</C:calendar-description>
+                    <CS:getctag>"ctag-1"</CS:getctag>
+                    <D:sync-token>sync-1</D:sync-token>
+                    <D:current-user-privilege-set>
+                      <D:privilege>
+                        <D:read />
+                      </D:privilege>
+                    </D:current-user-privilege-set>
+                    <C:calendar-timezone><![CDATA[
+                    BEGIN:VCALENDAR
+                    BEGIN:VTIMEZONE
+                    TZID:Europe/Warsaw
+                    END:VTIMEZONE
+                    END:VCALENDAR
+                    ]]></C:calendar-timezone>
+                    <C:supported-calendar-component-set>
+                      <C:comp name="VEVENT" />
+                      <C:comp name="VTODO" />
+                    </C:supported-calendar-component-set>
+                    <C:schedule-calendar-transp>
+                      <C:transparent />
+                    </C:schedule-calendar-transp>
+                    <ICAL:calendar-color>#5b617aff</ICAL:calendar-color>
+                    <ICAL:calendar-order>2</ICAL:calendar-order>
+                  </D:prop>
+                </D:propstat>
+              </D:response>
+              <D:response>
+                <D:href>/calendars/tasks/</D:href>
+                <D:propstat>
+                  <D:status>HTTP/1.1 200 OK</D:status>
+                  <D:prop>
+                    <D:resourcetype>
+                      <D:collection />
+                      <C:calendar />
+                    </D:resourcetype>
+                    <D:displayname>Tasks</D:displayname>
+                    <C:supported-calendar-component-set>
+                      <C:comp name="VTODO" />
+                    </C:supported-calendar-component-set>
+                  </D:prop>
+                </D:propstat>
+              </D:response>
+            </D:multistatus>
+            """);
+
+        var calendars = ParseCalendars(xml, new Uri("https://calendar.example.com/"));
+
+        calendars.Should().ContainSingle();
+
+        var calendar = calendars[0];
+        calendar.RemoteCalendarId.Should().Be("https://calendar.example.com/calendars/work");
+        calendar.Name.Should().Be("Work");
+        calendar.Description.Should().Be("Team calendar");
+        calendar.CTag.Should().Be("\"ctag-1\"");
+        calendar.SyncToken.Should().Be("sync-1");
+        calendar.TimeZone.Should().Be("Europe/Warsaw");
+        calendar.BackgroundColorHex.Should().Be("#5B617A");
+        calendar.IsReadOnly.Should().BeTrue();
+        calendar.SupportsEvents.Should().BeTrue();
+        calendar.DefaultShowAs.Should().Be(CalendarItemShowAs.Free);
+        calendar.Order.Should().Be(2d);
+    }
+
+    [Fact]
+    public async Task SynchronizeCalendarMetadataAsync_UpdatesServerBackedSettingsAndPreservesUserColorOverride()
+    {
+        var tempDirectory = CreateTempDirectory();
+
+        var serverInformation = new CustomServerInformation
+        {
+            Id = Guid.NewGuid(),
+            IncomingServer = "imap.example.com",
+            IncomingServerPort = "993",
+            IncomingServerUsername = "user@example.com",
+            IncomingServerPassword = "password",
+            OutgoingServer = "smtp.example.com",
+            OutgoingServerPort = "587",
+            OutgoingServerUsername = "user@example.com",
+            OutgoingServerPassword = "password",
+            MaxConcurrentClients = 5,
+            CalendarSupportMode = ImapCalendarSupportMode.CalDav
+        };
+
+        var account = new MailAccount
+        {
+            Id = Guid.NewGuid(),
+            Name = "IMAP Test",
+            Address = "test@example.com",
+            ProviderType = MailProviderType.IMAP4,
+            IsCalendarAccessGranted = true,
+            ServerInformation = serverInformation
+        };
+
+        var localCalendar = new AccountCalendar
+        {
+            Id = Guid.NewGuid(),
+            AccountId = account.Id,
+            RemoteCalendarId = "https://calendar.example.com/calendars/work",
+            Name = "Local",
+            BackgroundColorHex = "#123456",
+            TextColorHex = "#FFFFFF",
+            IsBackgroundColorUserOverridden = true,
+            TimeZone = "UTC",
+            IsReadOnly = false,
+            DefaultShowAs = CalendarItemShowAs.Busy
+        };
+
+        var changeProcessor = new Mock<IImapChangeProcessor>();
+        changeProcessor
+            .Setup(x => x.GetAccountCalendarsAsync(account.Id))
+            .ReturnsAsync(new List<AccountCalendar> { localCalendar });
+        changeProcessor
+            .Setup(x => x.UpdateAccountCalendarAsync(It.IsAny<AccountCalendar>()))
+            .Returns(Task.CompletedTask);
+        changeProcessor
+            .Setup(x => x.DeleteCalendarIcsForCalendarAsync(It.IsAny<Guid>(), It.IsAny<Guid>()))
+            .Returns(Task.CompletedTask);
+        changeProcessor
+            .Setup(x => x.DeleteAccountCalendarAsync(It.IsAny<AccountCalendar>()))
+            .Returns(Task.CompletedTask);
+        changeProcessor
+            .Setup(x => x.InsertAccountCalendarAsync(It.IsAny<AccountCalendar>()))
+            .Returns(Task.CompletedTask);
+
+        var synchronizer = CreateSynchronizer(tempDirectory, account, changeProcessor.Object);
+
+        try
+        {
+            await InvokePrivateAsync(
+                synchronizer,
+                "SynchronizeCalendarMetadataAsync",
+                new List<CalDavCalendar>
+                {
+                    new()
+                    {
+                        RemoteCalendarId = localCalendar.RemoteCalendarId,
+                        Name = "Remote",
+                        TimeZone = "Europe/Warsaw",
+                        BackgroundColorHex = "#ABCDEF",
+                        IsReadOnly = true,
+                        DefaultShowAs = CalendarItemShowAs.Free,
+                        Order = 0
+                    }
+                });
+
+            localCalendar.Name.Should().Be("Remote");
+            localCalendar.TimeZone.Should().Be("Europe/Warsaw");
+            localCalendar.IsReadOnly.Should().BeTrue();
+            localCalendar.DefaultShowAs.Should().Be(CalendarItemShowAs.Free);
+            localCalendar.IsPrimary.Should().BeTrue();
+            localCalendar.BackgroundColorHex.Should().Be("#123456");
+            localCalendar.TextColorHex.Should().Be(ColorHelpers.GetReadableTextColorHex("#123456"));
+
+            changeProcessor.Verify(x => x.UpdateAccountCalendarAsync(localCalendar), Times.Once);
+            changeProcessor.Verify(x => x.InsertAccountCalendarAsync(It.IsAny<AccountCalendar>()), Times.Never);
+            changeProcessor.Verify(x => x.DeleteAccountCalendarAsync(It.IsAny<AccountCalendar>()), Times.Never);
+        }
+        finally
+        {
+            await synchronizer.KillSynchronizerAsync();
+            DeleteDirectory(tempDirectory);
+        }
+    }
+
+    private static List<CalDavCalendar> ParseCalendars(XDocument xml, Uri baseUri)
+    {
+        var parseMethod = typeof(CalDavClient).GetMethod(
+            "ParseCalendarCollection",
+            BindingFlags.NonPublic | BindingFlags.Static);
+
+        parseMethod.Should().NotBeNull();
+
+        var result = parseMethod!.Invoke(null, [xml, baseUri]);
+        return result.Should().BeOfType<List<CalDavCalendar>>().Subject;
+    }
+
+    private static ImapSynchronizer CreateSynchronizer(string appDataFolder, MailAccount account, IImapChangeProcessor changeProcessor)
+    {
+        var applicationConfiguration = new Mock<IApplicationConfiguration>();
+        applicationConfiguration.SetupProperty(x => x.ApplicationDataFolderPath, appDataFolder);
+        applicationConfiguration.SetupProperty(x => x.PublisherSharedFolderPath, appDataFolder);
+        applicationConfiguration.SetupProperty(x => x.ApplicationTempFolderPath, appDataFolder);
+        applicationConfiguration.SetupGet(x => x.SentryDNS).Returns(string.Empty);
+
+        var unifiedSynchronizer = new UnifiedImapSynchronizer(
+            Mock.Of<IFolderService>(),
+            Mock.Of<IMailService>(),
+            Mock.Of<IImapSynchronizerErrorHandlerFactory>());
+
+        return new ImapSynchronizer(
+            account,
+            changeProcessor,
+            applicationConfiguration.Object,
+            unifiedSynchronizer,
+            Mock.Of<IImapSynchronizerErrorHandlerFactory>(),
+            Mock.Of<ICalDavClient>(),
+            Mock.Of<IAutoDiscoveryService>(),
+            Mock.Of<ICalendarService>());
+    }
+
+    private static string CreateTempDirectory()
+    {
+        var path = Path.Combine(Path.GetTempPath(), "wino-caldav-calendar-tests", Guid.NewGuid().ToString("N"));
+        Directory.CreateDirectory(path);
+        return path;
+    }
+
+    private static void DeleteDirectory(string path)
+    {
+        if (Directory.Exists(path))
+        {
+            Directory.Delete(path, recursive: true);
+        }
+    }
+
+    private static async Task InvokePrivateAsync(object instance, string methodName, params object[] parameters)
+    {
+        var method = instance.GetType().GetMethod(methodName, BindingFlags.NonPublic | BindingFlags.Instance)
+                     ?? throw new InvalidOperationException($"Method '{methodName}' not found.");
+
+        var task = (Task)method.Invoke(instance, parameters)!;
+        await task.ConfigureAwait(false);
+    }
+}

Wino.Core.ViewModels/PersonalizationPageViewModel.cs

@@ -389,6 +389,24 @@ public partial class PersonalizationPageViewModel : CoreBaseViewModel
         public bool HasReadReceiptTracking { get; } = false;
         public bool IsReadReceiptAcknowledged { get; } = false;
         public string ReadReceiptDisplayText { get; } = string.Empty;
+        public IReadOnlyList<MailCategory> Categories { get; } =
+        [
+            new()
+            {
+                Id = Guid.NewGuid(),
+                Name = "Follow Up",
+                BackgroundColorHex = "#DCEBFF",
+                TextColorHex = "#0B5CAD"
+            },
+            new()
+            {
+                Id = Guid.NewGuid(),
+                Name = "Planning",
+                BackgroundColorHex = "#DDF5D7",
+                TextColorHex = "#236A1E"
+            }
+        ];
+        public bool HasCategories => Categories.Count > 0;
         public AccountContact SenderContact { get; } = null;
         event PropertyChangedEventHandler INotifyPropertyChanged.PropertyChanged
         {

Wino.Core/Synchronizers/ImapSynchronizer.cs

@@ -1522,7 +1522,7 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
             .ToDictionary(g => g.Key, g => g.First(), StringComparer.OrdinalIgnoreCase);
         var usedCalendarColors = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
 
-        var remotePrimaryCalendarId = remoteCalendars.FirstOrDefault()?.RemoteCalendarId;
+        var remotePrimaryCalendarId = GetPrimaryCalDavCalendarId(remoteCalendars);
 
         foreach (var localCalendar in localCalendars.ToList())
         {
@@ -1545,6 +1545,7 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
 
             if (existingLocal == null)
             {
+                var insertedCalendarColor = ResolveSynchronizedCalendarBackgroundColor(remoteCalendar.BackgroundColorHex, null, usedCalendarColors);
                 var newCalendar = new AccountCalendar
                 {
                     Id = Guid.NewGuid(),
@@ -1552,10 +1553,12 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
                     RemoteCalendarId = remoteCalendar.RemoteCalendarId,
                     Name = remoteCalendar.Name,
                     IsPrimary = isPrimary,
+                    IsReadOnly = remoteCalendar.IsReadOnly,
                     IsSynchronizationEnabled = true,
                     IsExtended = true,
-                    BackgroundColorHex = ColorHelpers.GetDistinctFlatColorHex(usedCalendarColors),
+                    DefaultShowAs = remoteCalendar.DefaultShowAs,
-                    TimeZone = "UTC",
+                    BackgroundColorHex = insertedCalendarColor,
+                    TimeZone = remoteCalendar.TimeZone,
                     SynchronizationDeltaToken = string.Empty
                 };
 
@@ -1565,10 +1568,15 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
                 continue;
             }
 
-            var resolvedColor = ColorHelpers.GetDistinctFlatColorHex(usedCalendarColors, existingLocal.BackgroundColorHex);
+            var resolvedColor = ResolveSynchronizedCalendarBackgroundColor(remoteCalendar.BackgroundColorHex, existingLocal, usedCalendarColors);
+            var resolvedTextColor = ColorHelpers.GetReadableTextColorHex(resolvedColor);
             var shouldUpdate = !string.Equals(existingLocal.Name, remoteCalendar.Name, StringComparison.Ordinal)
+                               || !string.Equals(existingLocal.TimeZone, remoteCalendar.TimeZone, StringComparison.OrdinalIgnoreCase)
+                               || existingLocal.IsReadOnly != remoteCalendar.IsReadOnly
+                               || existingLocal.DefaultShowAs != remoteCalendar.DefaultShowAs
                                || existingLocal.IsPrimary != isPrimary
-                               || !string.Equals(existingLocal.BackgroundColorHex, resolvedColor, StringComparison.OrdinalIgnoreCase);
+                               || !string.Equals(existingLocal.BackgroundColorHex, resolvedColor, StringComparison.OrdinalIgnoreCase)
+                               || !string.Equals(existingLocal.TextColorHex, resolvedTextColor, StringComparison.OrdinalIgnoreCase);
 
             if (!shouldUpdate)
             {
@@ -1577,14 +1585,54 @@ public class ImapSynchronizer : WinoSynchronizer<ImapRequest, ImapMessageCreatio
             }
 
             existingLocal.Name = remoteCalendar.Name;
+            existingLocal.TimeZone = remoteCalendar.TimeZone;
+            existingLocal.IsReadOnly = remoteCalendar.IsReadOnly;
+            existingLocal.DefaultShowAs = remoteCalendar.DefaultShowAs;
             existingLocal.IsPrimary = isPrimary;
             existingLocal.BackgroundColorHex = resolvedColor;
-            existingLocal.TextColorHex = ColorHelpers.GetReadableTextColorHex(existingLocal.BackgroundColorHex);
+            existingLocal.TextColorHex = resolvedTextColor;
             usedCalendarColors.Add(existingLocal.BackgroundColorHex);
             await _imapChangeProcessor.UpdateAccountCalendarAsync(existingLocal).ConfigureAwait(false);
         }
     }
 
+    private static string GetPrimaryCalDavCalendarId(IReadOnlyList<CalDavCalendar> remoteCalendars)
+    {
+        if (remoteCalendars == null || remoteCalendars.Count == 0)
+            return string.Empty;
+
+        if (remoteCalendars.Any(calendar => calendar.Order.HasValue))
+        {
+            return remoteCalendars
+                .OrderBy(calendar => calendar.Order ?? double.MaxValue)
+                .ThenBy(calendar => calendar.Name, StringComparer.OrdinalIgnoreCase)
+                .Select(calendar => calendar.RemoteCalendarId)
+                .FirstOrDefault() ?? string.Empty;
+        }
+
+        return remoteCalendars.First().RemoteCalendarId;
+    }
+
+    private static string ResolveSynchronizedCalendarBackgroundColor(
+        string remoteBackgroundColor,
+        AccountCalendar accountCalendar,
+        ISet<string> usedCalendarColors = null)
+    {
+        if (accountCalendar?.IsBackgroundColorUserOverridden == true)
+            return accountCalendar.BackgroundColorHex;
+
+        var preferredColor = string.IsNullOrWhiteSpace(remoteBackgroundColor)
+            ? accountCalendar?.BackgroundColorHex
+            : remoteBackgroundColor;
+
+        if (string.IsNullOrWhiteSpace(remoteBackgroundColor) && usedCalendarColors != null)
+            return ColorHelpers.GetDistinctFlatColorHex(usedCalendarColors, preferredColor);
+
+        return string.IsNullOrWhiteSpace(preferredColor)
+            ? ColorHelpers.GenerateFlatColorHex()
+            : preferredColor;
+    }
+
     private interface IImapCalendarOperationHandler
     {
         bool RequiresConnectedClient { get; }

Wino.Mail.ViewModels.Tests/Collections/WinoMailCollectionTests.cs

@@ -6,6 +6,7 @@ using FluentAssertions;
 using Wino.Core.Domain.Entities.Mail;
 using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.MailItem;
 using Wino.Mail.ViewModels.Collections;
 using Wino.Mail.ViewModels.Data;
 using Xunit;
@@ -167,7 +168,7 @@ public class WinoMailCollectionTests
                 groupItems.Add(item);
             }
 
-            groups.Add(((DateTime)group.Key, groupItems));
+            groups.Add((((MailListGroupKey)group.Key).Value is DateTime keyDate ? keyDate : default, groupItems));
         }
 
         groups.Should().NotBeEmpty();
@@ -188,6 +189,45 @@ public class WinoMailCollectionTests
         }
     }
 
+    [Fact]
+    public async Task AddRangeAsync_ShouldPlacePinnedItemsBeforeUnpinnedItems()
+    {
+        var sut = CreateCollection();
+        var olderPinned = CreateMailCopy(threadId: "pinned", creationDate: DateTime.UtcNow.AddDays(-3));
+        olderPinned.IsPinned = true;
+
+        var newerUnpinned = CreateMailCopy(threadId: "regular", creationDate: DateTime.UtcNow);
+
+        await sut.AddRangeAsync(
+            [
+                new MailItemViewModel(newerUnpinned),
+                new MailItemViewModel(olderPinned)
+            ],
+            clearIdCache: true);
+
+        var firstItem = FlattenItems(sut).First().Should().BeOfType<MailItemViewModel>().Subject;
+        firstItem.MailCopy.UniqueId.Should().Be(olderPinned.UniqueId);
+    }
+
+    [Fact]
+    public async Task UpdateMailCopy_ShouldMovePinnedItemToTop()
+    {
+        var sut = CreateCollection();
+        var older = CreateMailCopy(threadId: "older", creationDate: DateTime.UtcNow.AddDays(-2));
+        var newer = CreateMailCopy(threadId: "newer", creationDate: DateTime.UtcNow);
+
+        await sut.AddAsync(older);
+        await sut.AddAsync(newer);
+
+        var updatedOlder = CloneMailCopy(older);
+        updatedOlder.IsPinned = true;
+
+        await sut.UpdateMailCopy(updatedOlder, EntityUpdateSource.Server, MailCopyChangeFlags.IsPinned);
+
+        var firstItem = FlattenItems(sut).First().Should().BeOfType<MailItemViewModel>().Subject;
+        firstItem.MailCopy.UniqueId.Should().Be(older.UniqueId);
+    }
+
     [Fact]
     public async Task UpdateMailCopy_ShouldMergeExistingSingles_WhenThreadIdChangesToMatch()
     {
@@ -371,6 +411,7 @@ public class WinoMailCollectionTests
             Importance = source.Importance,
             IsRead = source.IsRead,
             IsFlagged = source.IsFlagged,
+            IsPinned = source.IsPinned,
             IsFocused = source.IsFocused,
             HasAttachments = source.HasAttachments,
             ItemType = source.ItemType,

Wino.Mail.ViewModels.Tests/Data/MailItemViewModelUpdateTests.cs

@@ -59,6 +59,29 @@ public class MailItemViewModelUpdateTests
             nameof(MailItemViewModel.SortingName));
     }
 
+    [Fact]
+    public void UpdateFrom_ShouldNotifyPinnedState_WhenPinnedChanges()
+    {
+        var original = CreateMailCopy("thread-1", DateTime.UtcNow);
+        var updated = CloneMailCopy(original);
+        updated.IsPinned = true;
+
+        var sut = new MailItemViewModel(original);
+        var raisedProperties = new List<string>();
+
+        sut.PropertyChanged += (_, e) =>
+        {
+            if (!string.IsNullOrEmpty(e.PropertyName))
+            {
+                raisedProperties.Add(e.PropertyName);
+            }
+        };
+
+        sut.UpdateFrom(updated);
+
+        raisedProperties.Should().Contain(nameof(MailItemViewModel.IsPinned));
+    }
+
     [Fact]
     public async Task UpdateMailCopy_ShouldNotifyThreadOnlyForReadState_WhenReadStateChanges()
     {
@@ -125,6 +148,7 @@ public class MailItemViewModelUpdateTests
             Importance = MailImportance.Normal,
             IsRead = false,
             IsFlagged = false,
+            IsPinned = false,
             IsFocused = false,
             HasAttachments = false,
             ItemType = MailItemType.Mail,
@@ -151,6 +175,7 @@ public class MailItemViewModelUpdateTests
             Importance = source.Importance,
             IsRead = source.IsRead,
             IsFlagged = source.IsFlagged,
+            IsPinned = source.IsPinned,
             IsFocused = source.IsFocused,
             HasAttachments = source.HasAttachments,
             ItemType = source.ItemType,

Wino.Mail.ViewModels/Collections/WinoMailCollection.cs

@@ -12,6 +12,7 @@ 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.Mail.ViewModels.Data;
 using Wino.Messaging.Client.Mails;
 using Wino.Messaging.UI;
@@ -139,10 +140,24 @@ public class WinoMailCollection : ObservableRecipient, IRecipient<SelectedItemsC
 
     private object GetGroupingKey(IMailListItem mailItem)
     {
+        if (mailItem.IsPinned)
+            return MailListGroupKey.Pinned;
+
         if (SortingType == SortingOptionType.ReceiveDate)
-            return mailItem.CreationDate.ToLocalTime().Date;
+            return new MailListGroupKey(false, mailItem.CreationDate.ToLocalTime().Date);
-        else
+
-            return mailItem.FromName;
+        return new MailListGroupKey(false, mailItem.FromName);
+    }
+
+    private bool ShouldReinsertForChanges(MailCopyChangeFlags changedProperties)
+    {
+        if ((changedProperties & (MailCopyChangeFlags.ThreadId | MailCopyChangeFlags.IsPinned)) != 0)
+            return true;
+
+        if (SortingType == SortingOptionType.ReceiveDate)
+            return (changedProperties & MailCopyChangeFlags.CreationDate) != 0;
+
+        return (changedProperties & (MailCopyChangeFlags.FromName | MailCopyChangeFlags.FromAddress)) != 0;
     }
 
     private void UpdateUniqueIdHashes(IMailHashContainer itemContainer, bool isAdd)
@@ -608,7 +623,7 @@ public class WinoMailCollection : ObservableRecipient, IRecipient<SelectedItemsC
             }
         });
 
-        if ((appliedChanges & MailCopyChangeFlags.ThreadId) != 0)
+        if (ShouldReinsertForChanges(appliedChanges))
         {
             await ReinsertUpdatedItemAsync(updatedItem, wasSelected, existingItem.IsBusy);
             return;
@@ -993,6 +1008,16 @@ public class WinoMailCollection : ObservableRecipient, IRecipient<SelectedItemsC
         if (updates.Count == 0)
             return;
 
+        if (changedProperties == MailCopyChangeFlags.None || ShouldReinsertForChanges(changedProperties))
+        {
+            foreach (var update in updates)
+            {
+                await UpdateExistingItemAsync(update.ItemContainer, update.UpdatedMail, mailUpdateSource, changedProperties);
+            }
+
+            return;
+        }
+
         await ExecuteUIThread(() =>
         {
             foreach (var update in updates)

Wino.Mail.ViewModels/Data/AccountContactViewModel.cs

@@ -1,6 +1,8 @@
 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.Interfaces;
 
@@ -71,6 +73,8 @@ public partial class AccountContactViewModel : ObservableObject, IMailItemDispla
     public bool HasReadReceiptTracking => false;
     public bool IsReadReceiptAcknowledged => false;
     public string ReadReceiptDisplayText => string.Empty;
+    public IReadOnlyList<MailCategory> Categories => [];
+    public bool HasCategories => false;
     public AccountContact SenderContact => new()
     {
         Address = Address,

Wino.Mail.ViewModels/Data/MailItemViewModel.cs

@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Linq;
 using CommunityToolkit.Mvvm.ComponentModel;
 using Wino.Core.Domain;
 using Wino.Core.Domain.Entities.Mail;
@@ -17,6 +18,7 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
     [ObservableProperty]
     [NotifyPropertyChangedFor(nameof(CreationDate))]
     [NotifyPropertyChangedFor(nameof(IsFlagged))]
+    [NotifyPropertyChangedFor(nameof(IsPinned))]
     [NotifyPropertyChangedFor(nameof(FromName))]
     [NotifyPropertyChangedFor(nameof(IsFocused))]
     [NotifyPropertyChangedFor(nameof(IsRead))]
@@ -38,6 +40,8 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
     [NotifyPropertyChangedFor(nameof(UniqueId))]
     [NotifyPropertyChangedFor(nameof(ContactPictureFileId))]
     [NotifyPropertyChangedFor(nameof(SenderContact))]
+    [NotifyPropertyChangedFor(nameof(Categories))]
+    [NotifyPropertyChangedFor(nameof(HasCategories))]
     public partial MailCopy MailCopy { get; set; } = mailCopy;
 
     [ObservableProperty]
@@ -82,6 +86,12 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         set => SetProperty(MailCopy.IsFlagged, value, MailCopy, (u, n) => u.IsFlagged = n);
     }
 
+    public bool IsPinned
+    {
+        get => MailCopy.IsPinned;
+        set => SetProperty(MailCopy.IsPinned, value, MailCopy, (u, n) => u.IsPinned = n);
+    }
+
     public string FromName
     {
         get => string.IsNullOrEmpty(MailCopy.FromName) ? MailCopy.FromAddress : MailCopy.FromName;
@@ -117,6 +127,10 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         _ => string.Empty
     };
 
+    public IReadOnlyList<MailCategory> Categories => MailCopy.Categories;
+
+    public bool HasCategories => Categories.Count > 0;
+
     public string DraftId
     {
         get => MailCopy.DraftId;
@@ -233,6 +247,7 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         {
             nameof(CreationDate) or nameof(SortingDate) => MailCopyChangeFlags.CreationDate,
             nameof(IsFlagged) => MailCopyChangeFlags.IsFlagged,
+            nameof(IsPinned) => MailCopyChangeFlags.IsPinned,
             nameof(FromName) or nameof(SortingName) => MailCopyChangeFlags.FromName,
             nameof(IsFocused) => MailCopyChangeFlags.IsFocused,
             nameof(IsRead) => MailCopyChangeFlags.IsRead,
@@ -254,6 +269,7 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
             nameof(FolderId) => MailCopyChangeFlags.FolderId,
             nameof(UniqueId) => MailCopyChangeFlags.UniqueId,
             nameof(ContactPictureFileId) or nameof(SenderContact) => MailCopyChangeFlags.SenderContact,
+            nameof(Categories) or nameof(HasCategories) => MailCopyChangeFlags.Categories,
             _ => MailCopyChangeFlags.None
         };
     }
@@ -293,12 +309,13 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
             changedFlags |= SetIfChanged(MailCopy.Importance, source.Importance, value => MailCopy.Importance = value, MailCopyChangeFlags.Importance);
             changedFlags |= SetIfChanged(MailCopy.IsRead, source.IsRead, value => MailCopy.IsRead = value, MailCopyChangeFlags.IsRead);
             changedFlags |= SetIfChanged(MailCopy.IsFlagged, source.IsFlagged, value => MailCopy.IsFlagged = value, MailCopyChangeFlags.IsFlagged);
+            changedFlags |= SetIfChanged(MailCopy.IsPinned, source.IsPinned, value => MailCopy.IsPinned = value, MailCopyChangeFlags.IsPinned);
             changedFlags |= SetIfChanged(MailCopy.IsFocused, source.IsFocused, value => MailCopy.IsFocused = value, MailCopyChangeFlags.IsFocused);
             changedFlags |= SetIfChanged(MailCopy.FileId, source.FileId, value => MailCopy.FileId = value, MailCopyChangeFlags.FileId);
             changedFlags |= SetIfChanged(MailCopy.ItemType, source.ItemType, value => MailCopy.ItemType = value, MailCopyChangeFlags.ItemType);
-            changedFlags |= SetIfChanged(MailCopy.SenderContact, source.SenderContact, value => MailCopy.SenderContact = value, MailCopyChangeFlags.SenderContact);
+            changedFlags |= SetIfChangedIfNotNull(MailCopy.SenderContact, source.SenderContact, value => MailCopy.SenderContact = value, MailCopyChangeFlags.SenderContact);
-            changedFlags |= SetIfChanged(MailCopy.AssignedAccount, source.AssignedAccount, value => MailCopy.AssignedAccount = value, MailCopyChangeFlags.AssignedAccount);
+            changedFlags |= SetIfChangedIfNotNull(MailCopy.AssignedAccount, source.AssignedAccount, value => MailCopy.AssignedAccount = value, MailCopyChangeFlags.AssignedAccount);
-            changedFlags |= SetIfChanged(MailCopy.AssignedFolder, source.AssignedFolder, value => MailCopy.AssignedFolder = value, MailCopyChangeFlags.AssignedFolder);
+            changedFlags |= SetIfChangedIfNotNull(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);
@@ -353,6 +370,14 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         return flag;
     }
 
+    private static MailCopyChangeFlags SetIfChangedIfNotNull<T>(T currentValue, T newValue, Action<T> setter, MailCopyChangeFlags flag) where T : class
+    {
+        if (newValue == null)
+            return MailCopyChangeFlags.None;
+
+        return SetIfChanged(currentValue, newValue, setter, flag);
+    }
+
     private void RaisePropertyChanges(MailCopyChangeFlags changedFlags)
     {
         if (changedFlags == MailCopyChangeFlags.None)
@@ -377,6 +402,9 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
         if ((changedFlags & MailCopyChangeFlags.IsFlagged) != 0)
             Queue(nameof(IsFlagged));
 
+        if ((changedFlags & MailCopyChangeFlags.IsPinned) != 0)
+            Queue(nameof(IsPinned));
+
         if ((changedFlags & MailCopyChangeFlags.FromName) != 0)
         {
             Queue(nameof(FromName));
@@ -454,9 +482,21 @@ public partial class MailItemViewModel(MailCopy mailCopy) : ObservableRecipient,
             Queue(nameof(SenderContact));
         }
 
+        if ((changedFlags & MailCopyChangeFlags.Categories) != 0)
+        {
+            Queue(nameof(Categories));
+            Queue(nameof(HasCategories));
+        }
+
         foreach (var changedProperty in changedProperties)
         {
             OnPropertyChanged(changedProperty);
         }
     }
+
+    public void UpdateCategories(IReadOnlyList<MailCategory> categories)
+    {
+        MailCopy.Categories = categories?.ToList() ?? [];
+        RaisePropertyChanges(MailCopyChangeFlags.Categories);
+    }
 }

Wino.Mail.ViewModels/Data/ThreadMailItemViewModel.cs

@@ -5,6 +5,7 @@ using System.ComponentModel;
 using System.Linq;
 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;
 using Wino.Core.Domain.Interfaces;
@@ -91,6 +92,11 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     /// </summary>
     public bool IsFlagged => ThreadEmails.Any(e => e.IsFlagged);
 
+    /// <summary>
+    /// Gets whether any email in this thread is pinned.
+    /// </summary>
+    public bool IsPinned => ThreadEmails.Any(e => e.IsPinned);
+
     /// <summary>
     /// Gets whether the latest email is focused
     /// </summary>
@@ -106,6 +112,13 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     public bool IsReadReceiptAcknowledged => newestMailViewModel?.IsReadReceiptAcknowledged ?? false;
 
     public string ReadReceiptDisplayText => newestMailViewModel?.ReadReceiptDisplayText ?? string.Empty;
+    public IReadOnlyList<MailCategory> Categories => ThreadEmails
+        .SelectMany(a => a.Categories)
+        .GroupBy(a => a.Id)
+        .Select(a => a.First())
+        .OrderBy(a => a.Name)
+        .ToList();
+    public bool HasCategories => ThreadEmails.Any(a => a.HasCategories);
 
     /// <summary>
     /// Gets whether any email in this thread is a draft
@@ -182,6 +195,7 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     [NotifyPropertyChangedFor(nameof(HasAttachments))]
     [NotifyPropertyChangedFor(nameof(IsCalendarEvent))]
     [NotifyPropertyChangedFor(nameof(IsFlagged))]
+    [NotifyPropertyChangedFor(nameof(IsPinned))]
     [NotifyPropertyChangedFor(nameof(IsFocused))]
     [NotifyPropertyChangedFor(nameof(IsRead))]
     [NotifyPropertyChangedFor(nameof(HasReadReceiptTracking))]
@@ -200,6 +214,8 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     [NotifyPropertyChangedFor(nameof(UniqueId))]
     [NotifyPropertyChangedFor(nameof(ContactPictureFileId))]
     [NotifyPropertyChangedFor(nameof(SenderContact))]
+    [NotifyPropertyChangedFor(nameof(Categories))]
+    [NotifyPropertyChangedFor(nameof(HasCategories))]
     public partial ObservableCollection<MailItemViewModel> ThreadEmails { get; set; } = [];
 
     private MailItemViewModel newestMailViewModel => _cachedNewestMailViewModel;
@@ -461,6 +477,12 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
                     Queue(nameof(ContactPictureFileId));
                     Queue(nameof(SenderContact));
                 }
+
+                if ((changedFlags & MailCopyChangeFlags.Categories) != 0)
+                {
+                    Queue(nameof(Categories));
+                    Queue(nameof(HasCategories));
+                }
             }
         }
 
@@ -473,6 +495,9 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
         if ((changedFlags & MailCopyChangeFlags.IsFlagged) != 0 || changedFlags == MailCopyChangeFlags.All)
             Queue(nameof(IsFlagged));
 
+        if ((changedFlags & MailCopyChangeFlags.IsPinned) != 0 || changedFlags == MailCopyChangeFlags.All)
+            Queue(nameof(IsPinned));
+
         if ((changedFlags & MailCopyChangeFlags.IsRead) != 0 || changedFlags == MailCopyChangeFlags.All)
             Queue(nameof(IsRead));
 
@@ -486,6 +511,12 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
         if ((changedFlags & MailCopyChangeFlags.IsDraft) != 0 || changedFlags == MailCopyChangeFlags.All)
             Queue(nameof(IsDraft));
 
+        if ((changedFlags & MailCopyChangeFlags.Categories) != 0 || changedFlags == MailCopyChangeFlags.All)
+        {
+            Queue(nameof(Categories));
+            Queue(nameof(HasCategories));
+        }
+
         foreach (var changedProperty in changedProperties)
         {
             OnPropertyChanged(changedProperty);

Wino.Mail.ViewModels/ImapCalDavSettingsPageViewModel.cs

@@ -613,6 +613,7 @@ public partial class ImapCalDavSettingsPageViewModel : MailBaseViewModel
         var normalizedEmail = !string.IsNullOrWhiteSpace(EmailAddress) && !EmailAddress.Contains('@')
             ? $"{EmailAddress}@icloud.com"
             : EmailAddress;
+        var iCloudMailboxUsername = GetICloudMailboxUsername(normalizedEmail);
 
         if (!string.IsNullOrWhiteSpace(accountCreationDialogResult?.SpecialImapProviderDetails?.SenderName))
             DisplayName = accountCreationDialogResult.SpecialImapProviderDetails.SenderName;
@@ -632,10 +633,10 @@ public partial class ImapCalDavSettingsPageViewModel : MailBaseViewModel
                 ApplySpecialProviderDefaults(
                     "imap.mail.me.com",
                     "993",
-                    normalizedEmail,
+                    iCloudMailboxUsername,
                     "smtp.mail.me.com",
                     "587",
-                    normalizedEmail,
+                    iCloudMailboxUsername,
                     Password,
                     "https://caldav.icloud.com/",
                     normalizedEmail,
@@ -714,6 +715,19 @@ public partial class ImapCalDavSettingsPageViewModel : MailBaseViewModel
             OutgoingServerPort = "587";
     }
 
+    private static string GetICloudMailboxUsername(string emailAddress)
+    {
+        if (string.IsNullOrWhiteSpace(emailAddress))
+            return string.Empty;
+
+        var normalizedAddress = emailAddress.Trim();
+        var atIndex = normalizedAddress.IndexOf('@');
+
+        return atIndex > 0
+            ? normalizedAddress[..atIndex]
+            : normalizedAddress;
+    }
+
     private static string ReplaceIfEmptyOrMatchingPrevious(string currentValue, string previousValue, string replacementValue)
     {
         var normalizedCurrentValue = currentValue?.Trim() ?? string.Empty;

Wino.Mail.ViewModels/MailListPageViewModel.cs

@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Collections.Concurrent;
 using System.Collections.ObjectModel;
 using System.Diagnostics;
 using System.Linq;
@@ -760,6 +761,17 @@ public partial class MailListPageViewModel : MailBaseViewModel,
         await _winoRequestDelegator.ExecuteAsync(accountId, requests).ConfigureAwait(false);
     }
 
+    public Task ChangePinnedStatusAsync(IEnumerable<MailItemViewModel> targetItems, bool isPinned)
+    {
+        var uniqueIds = targetItems?
+            .Where(a => a?.MailCopy != null)
+            .Select(a => a.MailCopy.UniqueId)
+            .Distinct()
+            .ToList() ?? [];
+
+        return _mailService.ChangePinnedStatusAsync(uniqueIds, isPinned);
+    }
+
     private bool ShouldPreventItemAdd(MailCopy mailItem)
     {
         bool condition = mailItem.IsRead
@@ -1317,6 +1329,8 @@ public partial class MailListPageViewModel : MailBaseViewModel,
 
     private async Task<List<MailItemViewModel>> PrepareMailViewModelsAsync(IEnumerable<MailCopy> mailItems, CancellationToken cancellationToken = default)
     {
+        await PopulateMailCategoriesAsync(mailItems, cancellationToken).ConfigureAwait(false);
+
         // Run ViewModel creation on background thread to avoid blocking UI
         return await Task.Run(() =>
         {
@@ -1330,6 +1344,38 @@ public partial class MailListPageViewModel : MailBaseViewModel,
         }, cancellationToken).ConfigureAwait(false);
     }
 
+    private async Task PopulateMailCategoriesAsync(IEnumerable<MailCopy> mailItems, CancellationToken cancellationToken)
+    {
+        var mails = mailItems?.Where(a => a != null).ToList() ?? [];
+        if (mails.Count == 0)
+            return;
+
+        var accountIdsByFolderId = ActiveFolder?.HandlingFolders?
+            .GroupBy(a => a.Id)
+            .ToDictionary(a => a.Key, a => a.First().MailAccountId) ?? new Dictionary<Guid, Guid>();
+
+        var mailsByAccount = mails
+            .GroupBy(mail => ResolveMailAccountId(mail, accountIdsByFolderId))
+            .Where(group => group.Key != Guid.Empty)
+            .ToList();
+
+        foreach (var groupedMails in mailsByAccount)
+        {
+            cancellationToken.ThrowIfCancellationRequested();
+
+            var categoriesByMail = await _mailCategoryService
+                .GetCategoriesByMailAsync(groupedMails.Key, groupedMails.Select(a => a.UniqueId))
+                .ConfigureAwait(false);
+
+            foreach (var mail in groupedMails)
+            {
+                mail.Categories = categoriesByMail.TryGetValue(mail.UniqueId, out var categories)
+                    ? categories.ToList()
+                    : [];
+            }
+        }
+    }
+
     private async Task<HashSet<Guid>> GetPendingOperationUniqueIdsForActiveFolderAccountsAsync(CancellationToken cancellationToken = default)
     {
         var pendingOperationUniqueIds = new HashSet<Guid>();
@@ -1553,13 +1599,28 @@ public partial class MailListPageViewModel : MailBaseViewModel,
                 }
             }
 
+            var initialExistingIds = new ConcurrentDictionary<Guid, bool>(MailCollection.MailCopyIdHashSet);
+            var localPinnedItems = new List<MailCopy>();
+
+            if (!isDoingOnlineSearch)
+            {
+                var pinnedOptions = CreateInitializationOptions(SearchQuery, MailCollection.MailCopyIdHashSet);
+                localPinnedItems = await _mailService.FetchPinnedMailsAsync(pinnedOptions, cancellationToken).ConfigureAwait(false);
+
+                foreach (var pinnedItem in localPinnedItems)
+                {
+                    initialExistingIds.TryAdd(pinnedItem.UniqueId, true);
+                }
+            }
+
             var initializationOptions = CreateInitializationOptions(
                 isDoingOnlineSearch ? string.Empty : SearchQuery,
-                MailCollection.MailCopyIdHashSet,
+                initialExistingIds,
                 onlineSearchItems,
                 isDoingOnlineSearch);
 
             items = await _mailService.FetchMailsAsync(initializationOptions, cancellationToken).ConfigureAwait(false);
+            items = localPinnedItems.Count > 0 ? [.. localPinnedItems, .. items] : items;
 
             if (!listManipulationCancellationTokenSource.IsCancellationRequested)
             {

Wino.Mail.ViewModels/MailRenderingPageViewModel.cs

@@ -499,7 +499,7 @@ public partial class MailRenderingPageViewModel : MailBaseViewModel,
             // Use the received date from MailCopy if available, otherwise fall back to the sent date from MIME message
             CreationDate = initializedMailItemViewModel?.MailCopy.CreationDate ?? message.Date.DateTime;
 
-            // Automatically disable images for Junk folder to prevent pixel tracking.
+            // Automatically block remote image loading for Junk folder to reduce pixel tracking.
             // This can only work for selected mail item rendering, not for EML file rendering.
             if (initializedMailItemViewModel != null &&
                 initializedMailItemViewModel.MailCopy.AssignedFolder.SpecialFolderType == SpecialFolderType.Junk)
@@ -604,6 +604,15 @@ public partial class MailRenderingPageViewModel : MailBaseViewModel,
         if (initializedMailItemViewModel == null)
             return;
 
+        var assignedFolder = initializedMailItemViewModel.MailCopy.AssignedFolder;
+
+        if (assignedFolder == null)
+        {
+            Log.Warning("Skipping folder-specific mail commands because AssignedFolder is missing for {MailUniqueId}",
+                initializedMailItemViewModel.MailCopy.UniqueId);
+            return;
+        }
+
         MenuItems.Add(MailOperationMenuItem.Create(MailOperation.Seperator));
 
         // You can't do these to draft items.
@@ -625,7 +634,7 @@ public partial class MailRenderingPageViewModel : MailBaseViewModel,
         }
 
         // Archive - Unarchive
-        if (initializedMailItemViewModel.MailCopy.AssignedFolder.SpecialFolderType == SpecialFolderType.Archive)
+        if (assignedFolder.SpecialFolderType == SpecialFolderType.Archive)
             MenuItems.Add(MailOperationMenuItem.Create(MailOperation.UnArchive));
         else
             MenuItems.Add(MailOperationMenuItem.Create(MailOperation.Archive));
@@ -647,10 +656,10 @@ public partial class MailRenderingPageViewModel : MailBaseViewModel,
         else
             MenuItems.Add(MailOperationMenuItem.Create(MailOperation.MarkAsRead, true, false));
 
-        if (initializedMailItemViewModel.MailCopy.AssignedFolder.SpecialFolderType == SpecialFolderType.Junk)
+        if (assignedFolder.SpecialFolderType == SpecialFolderType.Junk)
             MenuItems.Add(MailOperationMenuItem.Create(MailOperation.MarkAsNotJunk, true, true));
         else if (!initializedMailItemViewModel.IsDraft &&
-                 initializedMailItemViewModel.MailCopy.AssignedFolder.SpecialFolderType != SpecialFolderType.Sent)
+                 assignedFolder.SpecialFolderType != SpecialFolderType.Sent)
             MenuItems.Add(MailOperationMenuItem.Create(MailOperation.MoveToJunk, true, true));
     }
 

Wino.Mail.ViewModels/MessageListPageViewModel.cs

@@ -4,6 +4,7 @@ using System.ComponentModel;
 using System.Threading.Tasks;
 using CommunityToolkit.Mvvm.Input;
 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.Interfaces;
@@ -187,6 +188,24 @@ public partial class MessageListPageViewModel : MailBaseViewModel
         public bool HasReadReceiptTracking => true;
         public bool IsReadReceiptAcknowledged => false;
         public string ReadReceiptDisplayText => Translator.MailReceiptStatus_Requested;
+        public IReadOnlyList<MailCategory> Categories =>
+        [
+            new()
+            {
+                Id = Guid.NewGuid(),
+                Name = "Urgent",
+                BackgroundColorHex = "#FFE1DE",
+                TextColorHex = "#A1260D"
+            },
+            new()
+            {
+                Id = Guid.NewGuid(),
+                Name = "Client",
+                BackgroundColorHex = "#E4E8FF",
+                TextColorHex = "#4255C5"
+            }
+        ];
+        public bool HasCategories => Categories.Count > 0;
         public AccountContact SenderContact => new()
         {
             Address = "hi@bkaan.dev",

Wino.Mail.ViewModels/SpecialImapCredentialsPageViewModel.cs

@@ -125,7 +125,7 @@ public partial class SpecialImapCredentialsPageViewModel : MailBaseViewModel
     {
         if (!CanProceed) return;
 
-        if (await _accountService.AccountAddressExistsAsync(EmailAddress).ConfigureAwait(false))
+        if (await _accountService.AccountAddressExistsAsync(EmailAddress))
         {
             await _dialogService.ShowMessageAsync(
                 Translator.DialogMessage_AccountAddressExistsMessage,

Wino.Mail.WinUI/Controls/MailItemDisplayInformationControl.xaml

@@ -8,6 +8,7 @@
     xmlns:domain="using:Wino.Core.Domain"
     xmlns:enums="using:Wino.Core.Domain.Enums"
     xmlns:helpers="using:Wino.Helpers"
+    xmlns:mail="using:Wino.Core.Domain.Entities.Mail"
     xmlns:muxc="using:Microsoft.UI.Xaml.Controls"
     HorizontalAlignment="Stretch"
     VerticalAlignment="Stretch"
@@ -23,6 +24,28 @@
     Unloaded="OnUnloaded">
 
     <UserControl.Resources>
+        <DataTemplate x:Key="DetailedMailCategoryTemplate" x:DataType="mail:MailCategory">
+            <Border
+                Margin="0,0,4,0"
+                Padding="6,2"
+                Background="{x:Bind helpers:XamlHelpers.GetSolidColorBrushFromHex(BackgroundColorHex), Mode=OneWay}"
+                CornerRadius="8">
+                <TextBlock
+                    Foreground="{x:Bind helpers:XamlHelpers.GetCategoryTextBrush(TextColorHex, BackgroundColorHex), Mode=OneWay}"
+                    Style="{StaticResource CaptionTextBlockStyle}"
+                    Text="{x:Bind Name, Mode=OneWay}"
+                    TextTrimming="CharacterEllipsis" />
+            </Border>
+        </DataTemplate>
+
+        <DataTemplate x:Key="CompactMailCategoryTemplate" x:DataType="mail:MailCategory">
+            <Ellipse
+                Width="8"
+                Height="8"
+                Margin="0,0,4,0"
+                Fill="{x:Bind helpers:XamlHelpers.GetSolidColorBrushFromHex(BackgroundColorHex), Mode=OneWay}" />
+        </DataTemplate>
+
         <Style
             x:Key="HoverActionButtonStyle"
             BasedOn="{StaticResource DefaultButtonStyle}"
@@ -89,6 +112,7 @@
                             <RowDefinition Height="Auto" />
                             <RowDefinition Height="Auto" />
                             <RowDefinition Height="Auto" />
+                            <RowDefinition Height="Auto" />
                         </Grid.RowDefinitions>
 
                         <!--  Sender + IsDraft + Hover Buttons  -->
@@ -206,6 +230,21 @@
                                 Text="{x:Bind helpers:XamlHelpers.GetMailItemDisplaySummaryForListing(MailItemInformation.IsDraft, MailItemInformation.CreationDate, Prefer24HourTimeFormat), Mode=OneWay}" />
                         </Grid>
 
+                        <ItemsControl
+                            x:Name="DetailedCategoriesContainer"
+                            Grid.Row="3"
+                            Margin="0,4,0,0"
+                            HorizontalAlignment="Left"
+                            ItemTemplate="{StaticResource DetailedMailCategoryTemplate}"
+                            ItemsSource="{x:Bind MailItemInformation.Categories, Mode=OneWay}"
+                            Visibility="{x:Bind helpers:XamlHelpers.CountToVisibilityConverter(MailItemInformation.Categories.Count), Mode=OneWay}">
+                            <ItemsControl.ItemsPanel>
+                                <ItemsPanelTemplate>
+                                    <StackPanel Orientation="Horizontal" />
+                                </ItemsPanelTemplate>
+                            </ItemsControl.ItemsPanel>
+                        </ItemsControl>
+
                         <!--  Message  -->
                         <Grid
                             x:Name="PreviewTextContainerRoot"
@@ -233,6 +272,18 @@
                                 Margin="4,4,1,4"
                                 Orientation="Horizontal"
                                 Spacing="2">
+                                <ItemsControl
+                                    x:Name="CompactCategoriesContainer"
+                                    VerticalAlignment="Center"
+                                    ItemTemplate="{StaticResource CompactMailCategoryTemplate}"
+                                    ItemsSource="{x:Bind MailItemInformation.Categories, Mode=OneWay}"
+                                    Visibility="Collapsed">
+                                    <ItemsControl.ItemsPanel>
+                                        <ItemsPanelTemplate>
+                                            <StackPanel Orientation="Horizontal" />
+                                        </ItemsPanelTemplate>
+                                    </ItemsControl.ItemsPanel>
+                                </ItemsControl>
 
                                 <TextBlock
                                     Margin="0,0,4,0"
@@ -288,8 +339,13 @@
             <VisualStateGroup x:Name="SizingStates">
                 <VisualState x:Name="Compact">
                     <VisualState.Setters>
-                        <Setter Target="RootContainer.Height" Value="60" />
+                        <Setter Target="RootContainer.Height" Value="64" />
-                        <Setter Target="ContentGrid.Padding" Value="8,0" />
+                        <Setter Target="ContentGrid.Padding" Value="8,6,8,6" />
+                        <Setter Target="ContentStackpanel.VerticalAlignment" Value="Center" />
+                        <Setter Target="PreviewTextContainerRoot.Margin" Value="0" />
+                        <Setter Target="IconsContainer.Margin" Value="4,0,1,0" />
+                        <Setter Target="DetailedCategoriesContainer.Visibility" Value="Collapsed" />
+                        <Setter Target="CompactCategoriesContainer.Visibility" Value="Visible" />
                         <Setter Target="PreviewTextContainer.Visibility" Value="Collapsed" />
                     </VisualState.Setters>
                     <VisualState.StateTriggers>
@@ -300,8 +356,13 @@
                 <!--  Medium  -->
                 <VisualState x:Name="Medium">
                     <VisualState.Setters>
-                        <Setter Target="RootContainer.Height" Value="80" />
+                        <Setter Target="RootContainer.Height" Value="96" />
-                        <Setter Target="ContentGrid.Padding" Value="6,0" />
+                        <Setter Target="ContentGrid.Padding" Value="6,8,6,6" />
+                        <Setter Target="ContentStackpanel.VerticalAlignment" Value="Top" />
+                        <Setter Target="DetailedCategoriesContainer.Margin" Value="0,2,0,0" />
+                        <Setter Target="PreviewTextContainerRoot.Margin" Value="0,2,0,0" />
+                        <Setter Target="IconsContainer.Margin" Value="4,2,1,0" />
+                        <Setter Target="CompactCategoriesContainer.Visibility" Value="Collapsed" />
                         <Setter Target="PreviewTextContainer.Visibility" Value="Visible" />
                     </VisualState.Setters>
                     <VisualState.StateTriggers>
@@ -314,6 +375,11 @@
                     <VisualState.Setters>
                         <Setter Target="RootContainer.Height" Value="Auto" />
                         <Setter Target="ContentGrid.Padding" Value="12,12,6,12" />
+                        <Setter Target="ContentStackpanel.VerticalAlignment" Value="Center" />
+                        <Setter Target="DetailedCategoriesContainer.Margin" Value="0,4,0,0" />
+                        <Setter Target="PreviewTextContainerRoot.Margin" Value="0" />
+                        <Setter Target="IconsContainer.Margin" Value="4,4,1,4" />
+                        <Setter Target="CompactCategoriesContainer.Visibility" Value="Collapsed" />
                         <Setter Target="PreviewTextContainer.Visibility" Value="Visible" />
                     </VisualState.Setters>
                     <VisualState.StateTriggers>

Wino.Mail.WinUI/Helpers/XamlHelpers.cs

@@ -16,6 +16,7 @@ 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.Models.MailItem;
 using Wino.Mail.WinUI.Controls;
 
 namespace Wino.Helpers;
@@ -151,6 +152,12 @@ public static class XamlHelpers
     public static Color GetWindowsColorFromHex(string hex) => hex.ToColor();
 
     public static SolidColorBrush GetSolidColorBrushFromHex(string colorHex) => string.IsNullOrEmpty(colorHex) ? new SolidColorBrush(Colors.Transparent) : new SolidColorBrush(colorHex.ToColor());
+    public static SolidColorBrush GetCategoryTextBrush(string textColorHex, string backgroundColorHex)
+        => !string.IsNullOrWhiteSpace(textColorHex)
+            ? GetSolidColorBrushFromHex(textColorHex)
+            : string.IsNullOrWhiteSpace(backgroundColorHex)
+                ? new SolidColorBrush(Colors.Black)
+                : GetReadableTextColor(backgroundColorHex);
     public static FontWeight GetFontWeightBySyncState(bool isSyncing) => isSyncing ? FontWeights.SemiBold : FontWeights.Normal;
 
     public static Brush GetWizardStepBadgeBrush(bool isActive)
@@ -184,6 +191,14 @@ public static class XamlHelpers
     }
     public static string GetMailGroupDateString(object groupObject)
     {
+        if (groupObject is MailListGroupKey pinnedGroupKey)
+        {
+            if (pinnedGroupKey.IsPinned)
+                return Translator.FolderCustomization_SectionPinned;
+
+            groupObject = pinnedGroupKey.Value!;
+        }
+
         if (groupObject is string stringObject)
             return stringObject;
 

Wino.Mail.WinUI/Views/Mail/MailListPage.xaml.cs

@@ -245,27 +245,36 @@ public sealed partial class MailListPage : MailListPageAbstract,
 
             // Default to all selected items.
             targetItems = ViewModel.MailCollection.SelectedItems;
+            var areAllPinned = targetItems.Any() && targetItems.All(item => item.MailCopy.IsPinned);
             var availableActions = ViewModel.GetAvailableMailActions(targetItems);
             var (availableCategories, assignedCategoryIds) = await ViewModel.GetAvailableCategoriesAsync(targetItems);
 
-            if (availableActions == null || !availableActions.Any()) return;
-
             var clickedAction = await GetMailContextActionFromFlyoutAsync(
                 availableActions,
                 availableCategories,
                 assignedCategoryIds,
+                areAllPinned,
                 control,
                 p.X,
                 p.Y);
 
             if (clickedAction == null) return;
 
+            if (clickedAction.PinState.HasValue)
+            {
+                await ViewModel.ChangePinnedStatusAsync(targetItems, clickedAction.PinState.Value);
+                return;
+            }
+
             if (clickedAction.Category != null)
             {
                 await ViewModel.ToggleCategoryAssignmentAsync(clickedAction.Category, targetItems, clickedAction.IsCategoryAssignedToAll);
                 return;
             }
 
+            if (clickedAction.Operation == null)
+                return;
+
             var prepRequest = new MailOperationPreperationRequest(clickedAction.Operation.Operation, targetItems.Select(a => a.MailCopy));
 
             await ViewModel.ExecuteMailOperationAsync(prepRequest);
@@ -313,6 +322,7 @@ public sealed partial class MailListPage : MailListPageAbstract,
         IEnumerable<MailOperationMenuItem> availableActions,
         IReadOnlyList<MailCategory> availableCategories,
         IReadOnlyCollection<Guid> assignedCategoryIds,
+        bool areAllPinned,
         UIElement showAtElement,
         double x,
         double y)
@@ -320,7 +330,7 @@ public sealed partial class MailListPage : MailListPageAbstract,
         var source = new TaskCompletionSource<MailContextAction?>();
         var flyout = new WinoMenuFlyout();
 
-        foreach (var action in availableActions)
+        foreach (var action in availableActions ?? [])
         {
             if (action.Operation == MailOperation.Seperator)
             {
@@ -337,6 +347,27 @@ public sealed partial class MailListPage : MailListPageAbstract,
             flyout.Items.Add(menuFlyoutItem);
         }
 
+        if (flyout.Items.Count > 0 && flyout.Items.LastOrDefault() is not MenuFlyoutSeparator)
+        {
+            flyout.Items.Add(new MenuFlyoutSeparator());
+        }
+
+        var pinItem = new MenuFlyoutItem
+        {
+            Text = areAllPinned ? Translator.FolderOperation_Unpin : Translator.FolderOperation_Pin,
+            Icon = new WinoFontIcon { Icon = areAllPinned ? WinoIconGlyph.UnPin : WinoIconGlyph.Pin }
+        };
+
+        MenuFlyoutLanguageHelper.Apply(pinItem);
+
+        pinItem.Click += (_, _) =>
+        {
+            source.TrySetResult(new MailContextAction(!areAllPinned));
+            flyout.Hide();
+        };
+
+        flyout.Items.Add(pinItem);
+
         if (availableCategories?.Count > 0)
         {
             if (flyout.Items.LastOrDefault() is not MenuFlyoutSeparator)
@@ -381,9 +412,13 @@ public sealed partial class MailListPage : MailListPageAbstract,
         return await source.Task;
     }
 
-    private sealed record MailContextAction(MailOperationMenuItem Operation, MailCategory Category = null, bool IsCategoryAssignedToAll = false)
+    private sealed record MailContextAction(MailOperationMenuItem? Operation = null, MailCategory? Category = null, bool IsCategoryAssignedToAll = false, bool? PinState = null)
     {
-        public MailContextAction(MailCategory category, bool isCategoryAssignedToAll) : this(null, category, isCategoryAssignedToAll)
+        public MailContextAction(MailCategory category, bool isCategoryAssignedToAll) : this((MailOperationMenuItem?)null, category, isCategoryAssignedToAll)
+        {
+        }
+
+        public MailContextAction(bool pinState) : this((MailOperationMenuItem?)null, (MailCategory?)null, false, pinState)
         {
         }
     }

Wino.Services/CalDavClient.cs

@@ -44,12 +44,19 @@ public sealed class CalDavClient : ICalDavClient
         var homeSetUri = await DiscoverCalendarHomeSetUriAsync(connectionSettings, principalUri, cancellationToken).ConfigureAwait(false);
 
         var body = """
-            <D:propfind xmlns:D="DAV:" xmlns:C="urn:ietf:params:xml:ns:caldav" xmlns:CS="http://calendarserver.org/ns/">
+            <D:propfind xmlns:D="DAV:" xmlns:C="urn:ietf:params:xml:ns:caldav" xmlns:CS="http://calendarserver.org/ns/" xmlns:ICAL="http://apple.com/ns/ical/">
               <D:prop>
                 <D:resourcetype />
                 <D:displayname />
+                <D:current-user-privilege-set />
                 <CS:getctag />
                 <D:sync-token />
+                <C:calendar-description />
+                <C:calendar-timezone />
+                <C:supported-calendar-component-set />
+                <C:schedule-calendar-transp />
+                <ICAL:calendar-color />
+                <ICAL:calendar-order />
               </D:prop>
             </D:propfind>
             """;
@@ -344,10 +351,32 @@ public sealed class CalDavClient : ICalDavClient
                     continue;
 
                 var displayName = prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "displayname")?.Value ?? string.Empty;
+                var description = prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "calendar-description")?.Value ?? string.Empty;
                 var ctag = prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "getctag")?.Value ?? string.Empty;
                 var syncToken = prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "sync-token")?.Value ?? string.Empty;
+                var timeZone = ExtractCalendarTimeZoneId(
+                    prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "calendar-timezone")?.Value);
+                var backgroundColor = NormalizeCalendarColor(
+                    prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "calendar-color")?.Value);
+                var supportedComponents = prop
+                    .Descendants()
+                    .Where(e => e.Name.LocalName == "supported-calendar-component-set")
+                    .Descendants()
+                    .Where(e => e.Name.LocalName == "comp")
+                    .Select(e => e.Attribute("name")?.Value?.Trim())
+                    .Where(value => !string.IsNullOrWhiteSpace(value))
+                    .ToList();
+                var supportsEvents = supportedComponents.Count == 0 ||
+                                     supportedComponents.Contains("VEVENT", StringComparer.OrdinalIgnoreCase);
+                var isReadOnly = IsCalendarReadOnly(prop);
+                var defaultShowAs = GetDefaultShowAs(prop);
+                var calendarOrder = ParseCalendarOrder(
+                    prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "calendar-order")?.Value);
                 var remoteUri = CreateAbsoluteUri(baseUri, href).ToString().TrimEnd('/');
 
+                if (!supportsEvents)
+                    continue;
+
                 if (string.IsNullOrWhiteSpace(displayName))
                 {
                     displayName = WebUtility.UrlDecode(remoteUri.Split('/').LastOrDefault() ?? "Calendar");
@@ -357,8 +386,15 @@ public sealed class CalDavClient : ICalDavClient
                 {
                     RemoteCalendarId = remoteUri,
                     Name = displayName,
+                    Description = description,
                     CTag = ctag,
-                    SyncToken = syncToken
+                    SyncToken = syncToken,
+                    TimeZone = timeZone,
+                    BackgroundColorHex = backgroundColor,
+                    IsReadOnly = isReadOnly,
+                    SupportsEvents = supportsEvents,
+                    DefaultShowAs = defaultShowAs,
+                    Order = calendarOrder
                 });
             }
         }
@@ -820,6 +856,152 @@ public sealed class CalDavClient : ICalDavClient
         return false;
     }
 
+    private static bool IsCalendarReadOnly(XElement prop)
+    {
+        var privilegeSet = prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "current-user-privilege-set");
+        if (privilegeSet == null)
+            return false;
+
+        var privilegeNames = privilegeSet
+            .Descendants()
+            .Where(e => e.Name.LocalName == "privilege")
+            .Descendants()
+            .Select(e => e.Name.LocalName)
+            .ToHashSet(StringComparer.OrdinalIgnoreCase);
+
+        return !privilegeNames.Contains("all")
+               && !privilegeNames.Contains("write")
+               && !privilegeNames.Contains("write-content");
+    }
+
+    private static CalendarItemShowAs GetDefaultShowAs(XElement prop)
+    {
+        var transparency = prop.Descendants().FirstOrDefault(e => e.Name.LocalName == "schedule-calendar-transp");
+        if (transparency?.Descendants().Any(e => e.Name.LocalName == "transparent") == true)
+            return CalendarItemShowAs.Free;
+
+        return CalendarItemShowAs.Busy;
+    }
+
+    private static double? ParseCalendarOrder(string value)
+    {
+        if (string.IsNullOrWhiteSpace(value))
+            return null;
+
+        return double.TryParse(value.Trim(), System.Globalization.NumberStyles.Float, System.Globalization.CultureInfo.InvariantCulture, out var result)
+            ? result
+            : null;
+    }
+
+    private static string ExtractCalendarTimeZoneId(string value)
+    {
+        if (string.IsNullOrWhiteSpace(value))
+            return string.Empty;
+
+        var unfoldedValue = UnfoldIcsText(TrimCommonIndentation(value));
+        foreach (var rawLine in unfoldedValue.Split('\n', StringSplitOptions.RemoveEmptyEntries))
+        {
+            var line = rawLine.Trim();
+            if (string.IsNullOrWhiteSpace(line))
+                continue;
+
+            var separatorIndex = line.IndexOf(':');
+            if (separatorIndex <= 0)
+                continue;
+
+            var propertyName = line[..separatorIndex];
+            var propertyValue = line[(separatorIndex + 1)..].Trim();
+
+            if (propertyName.StartsWith("TZID", StringComparison.OrdinalIgnoreCase) && !string.IsNullOrWhiteSpace(propertyValue))
+                return propertyValue;
+
+            if (propertyName.StartsWith("X-WR-TIMEZONE", StringComparison.OrdinalIgnoreCase) && !string.IsNullOrWhiteSpace(propertyValue))
+                return propertyValue;
+        }
+
+        return value.Trim();
+    }
+
+    private static string UnfoldIcsText(string value)
+    {
+        var normalizedValue = value
+            .Replace("\r\n", "\n", StringComparison.Ordinal)
+            .Replace('\r', '\n');
+        var unfoldedLines = new List<string>();
+
+        foreach (var rawLine in normalizedValue.Split('\n'))
+        {
+            if ((rawLine.StartsWith(' ') || rawLine.StartsWith('\t')) && unfoldedLines.Count > 0)
+            {
+                unfoldedLines[^1] += rawLine.TrimStart(' ', '\t');
+                continue;
+            }
+
+            unfoldedLines.Add(rawLine);
+        }
+
+        return string.Join("\n", unfoldedLines);
+    }
+
+    private static string TrimCommonIndentation(string value)
+    {
+        var normalizedValue = value
+            .Replace("\r\n", "\n", StringComparison.Ordinal)
+            .Replace('\r', '\n');
+        var lines = normalizedValue.Split('\n');
+        var nonEmptyLines = lines
+            .Where(line => !string.IsNullOrWhiteSpace(line))
+            .ToList();
+
+        if (nonEmptyLines.Count == 0)
+            return normalizedValue;
+
+        var commonIndentation = nonEmptyLines
+            .Select(line => line.TakeWhile(ch => ch is ' ' or '\t').Count())
+            .Min();
+
+        if (commonIndentation <= 0)
+            return normalizedValue;
+
+        return string.Join(
+            "\n",
+            lines.Select(line =>
+            {
+                if (string.IsNullOrWhiteSpace(line))
+                    return string.Empty;
+
+                return line.Length >= commonIndentation
+                    ? line[commonIndentation..]
+                    : line.TrimStart(' ', '\t');
+            }));
+    }
+
+    private static string NormalizeCalendarColor(string value)
+    {
+        if (string.IsNullOrWhiteSpace(value))
+            return string.Empty;
+
+        var color = value.Trim();
+        if (color.StartsWith('#'))
+        {
+            color = color[1..];
+        }
+
+        if (color.Length == 8)
+        {
+            color = color[..6];
+        }
+        else if (color.Length == 3)
+        {
+            color = string.Concat(color.Select(c => $"{c}{c}"));
+        }
+
+        if (color.Length != 6 || !int.TryParse(color, System.Globalization.NumberStyles.HexNumber, System.Globalization.CultureInfo.InvariantCulture, out _))
+            return string.Empty;
+
+        return $"#{color.ToUpperInvariant()}";
+    }
+
     private static Uri CreateAbsoluteUri(Uri baseUri, string href)
     {
         if (Uri.TryCreate(href, UriKind.Absolute, out var absolute))

Wino.Services/DatabaseService.cs

@@ -81,6 +81,15 @@ public class DatabaseService : IDatabaseService
     {
         await EnsureKeyboardShortcutSchemaAsync().ConfigureAwait(false);
 
+        var mailCopyColumns = await Connection.GetTableInfoAsync(nameof(MailCopy)).ConfigureAwait(false);
+
+        if (!mailCopyColumns.Any(c => c.Name == nameof(MailCopy.IsPinned)))
+        {
+            await Connection
+                .ExecuteAsync($"ALTER TABLE {nameof(MailCopy)} ADD COLUMN {nameof(MailCopy.IsPinned)} INTEGER NOT NULL DEFAULT 0")
+                .ConfigureAwait(false);
+        }
+
         var accountColumns = await Connection.GetTableInfoAsync(nameof(MailAccount)).ConfigureAwait(false);
 
         if (!accountColumns.Any(c => c.Name == nameof(MailAccount.CreatedAt)))

Wino.Services/Extensions/HtmlAgilityPackExtensions.cs

@@ -1,6 +1,7 @@
-using System;
+using System;
 using System.IO;
 using System.Linq;
+using System.Text.RegularExpressions;
 using HtmlAgilityPack;
 
 namespace Wino.Services.Extensions;
@@ -8,16 +9,64 @@ namespace Wino.Services.Extensions;
 public static class HtmlAgilityPackExtensions
 {
     /// <summary>
-    /// Clears out the src attribute for all `img` and `v:fill` tags.
+    /// Clears passive remote image-loading hooks while preserving already-embedded inline images.
     /// </summary>
-    /// <param name="document"></param>
     public static void ClearImages(this HtmlDocument document)
     {
-        if (document.DocumentNode.InnerHtml.Contains("<img"))
+        if (document?.DocumentNode == null)
         {
-            foreach (var eachNode in document.DocumentNode.SelectNodes("//img"))
+            return;
+        }
+
+        foreach (var eachNode in document.DocumentNode.Descendants().ToList())
+        {
+            ClearRemoteImageAttribute(eachNode, "src");
+            ClearRemoteImageAttribute(eachNode, "background");
+            ClearRemoteImageAttribute(eachNode, "poster");
+            ClearRemoteImageAttribute(eachNode, "data");
+
+            if (eachNode.Attributes.Contains("srcset"))
             {
-                eachNode.Attributes.Remove("src");
+                eachNode.Attributes.Remove("srcset");
+            }
+
+            if (eachNode.Attributes.Contains("imagesrcset"))
+            {
+                eachNode.Attributes.Remove("imagesrcset");
+            }
+
+            if (eachNode.Attributes.Contains("style"))
+            {
+                var sanitizedStyle = SanitizeCss(eachNode.GetAttributeValue("style", string.Empty));
+
+                if (string.IsNullOrWhiteSpace(sanitizedStyle))
+                {
+                    eachNode.Attributes.Remove("style");
+                }
+                else
+                {
+                    eachNode.SetAttributeValue("style", sanitizedStyle);
+                }
+            }
+
+            if (IsSvgImageReferenceElement(eachNode))
+            {
+                ClearRemoteImageAttribute(eachNode, "href");
+                ClearRemoteImageAttribute(eachNode, "xlink:href");
+            }
+        }
+
+        foreach (var styleNode in document.DocumentNode.Descendants("style").ToList())
+        {
+            var sanitizedCss = SanitizeCss(styleNode.InnerHtml);
+
+            if (string.IsNullOrWhiteSpace(sanitizedCss))
+            {
+                styleNode.Remove();
+            }
+            else
+            {
+                styleNode.InnerHtml = sanitizedCss;
             }
         }
     }
@@ -116,4 +165,47 @@ public static class HtmlAgilityPackExtensions
                 break;
         }
     }
+
+    private static void ClearRemoteImageAttribute(HtmlNode node, string attributeName)
+    {
+        var value = node.GetAttributeValue(attributeName, null);
+
+        if (string.IsNullOrWhiteSpace(value))
+        {
+            return;
+        }
+
+        if (!IsEmbeddedImageSource(value))
+        {
+            node.Attributes.Remove(attributeName);
+        }
+    }
+
+    private static bool IsEmbeddedImageSource(string value)
+    {
+        var trimmed = value.Trim().Trim('"', '\'');
+
+        return trimmed.StartsWith("data:image/", StringComparison.OrdinalIgnoreCase)
+               || trimmed.StartsWith("cid:", StringComparison.OrdinalIgnoreCase)
+               || trimmed.StartsWith('#');
+    }
+
+    private static bool IsSvgImageReferenceElement(HtmlNode node)
+        => node.Name.Equals("image", StringComparison.OrdinalIgnoreCase)
+           || node.Name.Equals("feImage", StringComparison.OrdinalIgnoreCase)
+           || node.Name.Equals("use", StringComparison.OrdinalIgnoreCase);
+
+    private static string SanitizeCss(string css)
+    {
+        if (string.IsNullOrWhiteSpace(css))
+        {
+            return string.Empty;
+        }
+
+        var sanitizedCss = Regex.Replace(css, @"(?is)url\s*\([^)]*\)", "none");
+        sanitizedCss = Regex.Replace(sanitizedCss, @"(?is)image-set\s*\([^)]*\)", "none");
+        sanitizedCss = Regex.Replace(sanitizedCss, @"(?is)@import\s+[^;]+;?", string.Empty);
+
+        return sanitizedCss.Trim();
+    }
 }

Wino.Services/MailCategoryService.cs

@@ -288,6 +288,39 @@ public class MailCategoryService : BaseDatabaseService, IMailCategoryService
             [accountId, .. uniqueIds.Cast<object>()]).ConfigureAwait(false);
     }
 
+    public async Task<IReadOnlyDictionary<Guid, IReadOnlyList<MailCategory>>> GetCategoriesByMailAsync(Guid accountId, IEnumerable<Guid> mailCopyUniqueIds)
+    {
+        var uniqueIds = mailCopyUniqueIds?.Distinct().ToList() ?? [];
+        if (uniqueIds.Count == 0)
+            return new Dictionary<Guid, IReadOnlyList<MailCategory>>();
+
+        var placeholders = string.Join(",", uniqueIds.Select(_ => "?"));
+        var sql =
+            $"SELECT {nameof(MailCategoryAssignment)}.{nameof(MailCategoryAssignment.MailCopyUniqueId)} as {nameof(MailCategoryRow.MailCopyUniqueId)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.Id)} as {nameof(MailCategoryRow.Id)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.MailAccountId)} as {nameof(MailCategoryRow.MailAccountId)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.RemoteId)} as {nameof(MailCategoryRow.RemoteId)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.Name)} as {nameof(MailCategoryRow.Name)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.IsFavorite)} as {nameof(MailCategoryRow.IsFavorite)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.BackgroundColorHex)} as {nameof(MailCategoryRow.BackgroundColorHex)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.TextColorHex)} as {nameof(MailCategoryRow.TextColorHex)}, " +
+            $"{nameof(MailCategory)}.{nameof(MailCategory.Source)} as {nameof(MailCategoryRow.Source)} " +
+            $"FROM {nameof(MailCategory)} " +
+            $"INNER JOIN {nameof(MailCategoryAssignment)} ON {nameof(MailCategory)}.{nameof(MailCategory.Id)} = {nameof(MailCategoryAssignment)}.{nameof(MailCategoryAssignment.MailCategoryId)} " +
+            $"WHERE {nameof(MailCategory)}.{nameof(MailCategory.MailAccountId)} = ? AND {nameof(MailCategoryAssignment)}.{nameof(MailCategoryAssignment.MailCopyUniqueId)} IN ({placeholders}) " +
+            $"ORDER BY {nameof(MailCategoryAssignment)}.{nameof(MailCategoryAssignment.MailCopyUniqueId)}, {nameof(MailCategory)}.{nameof(MailCategory.Name)} COLLATE NOCASE";
+
+        var rows = await Connection.QueryAsync<MailCategoryRow>(
+            sql,
+            [accountId, .. uniqueIds.Cast<object>()]).ConfigureAwait(false);
+
+        return rows
+            .GroupBy(a => a.MailCopyUniqueId)
+            .ToDictionary(
+                a => a.Key,
+                a => (IReadOnlyList<MailCategory>)a.Select(static row => row.ToMailCategory()).ToList());
+    }
+
     public async Task<List<Guid>> GetAssignedCategoryIdsForAllAsync(IEnumerable<Guid> mailCopyUniqueIds)
     {
         var uniqueIds = mailCopyUniqueIds?.Distinct().ToList() ?? [];
@@ -355,4 +388,21 @@ public class MailCategoryService : BaseDatabaseService, IMailCategoryService
 
     private static string NormalizeCategoryName(string name)
         => name?.Trim() ?? string.Empty;
+
+    private sealed class MailCategoryRow : MailCategory
+    {
+        public Guid MailCopyUniqueId { get; set; }
+
+        public MailCategory ToMailCategory() => new()
+        {
+            Id = Id,
+            MailAccountId = MailAccountId,
+            RemoteId = RemoteId,
+            Name = Name,
+            IsFavorite = IsFavorite,
+            BackgroundColorHex = BackgroundColorHex,
+            TextColorHex = TextColorHex,
+            Source = Source
+        };
+    }
 }

Wino.Services/MailService.cs

@@ -158,7 +158,7 @@ public class MailService : BaseDatabaseService, IMailService
         return await HydrateMailCopyAsync(mailCopy).ConfigureAwait(false);
     }
 
-    private static (string Query, object[] Parameters) BuildMailFetchQuery(MailListInitializationOptions options)
+    private static (string Query, object[] Parameters) BuildMailFetchQuery(MailListInitializationOptions options, bool pinnedOnly = false)
     {
         var sql = new StringBuilder();
         sql.Append(options.IsCategoryView
@@ -194,6 +194,11 @@ public class MailService : BaseDatabaseService, IMailService
                 break;
         }
 
+        if (pinnedOnly)
+        {
+            whereClauses.Add("MailCopy.IsPinned = 1");
+        }
+
         // Focused filter
         if (options.IsFocusedOnly != null)
         {
@@ -227,23 +232,26 @@ public class MailService : BaseDatabaseService, IMailService
 
         // Sorting
         if (options.SortingOptionType == SortingOptionType.ReceiveDate)
-            sql.Append(" ORDER BY CreationDate DESC");
+            sql.Append(" ORDER BY IsPinned DESC, CreationDate DESC");
         else if (options.SortingOptionType == SortingOptionType.Sender)
-            sql.Append(" ORDER BY FromName ASC");
+            sql.Append(" ORDER BY IsPinned DESC, FromName ASC, CreationDate DESC");
 
         // Pagination
-        var limit = options.Take > 0 ? options.Take : ItemLoadCount;
+        if (!pinnedOnly)
-        sql.Append($" LIMIT {limit}");
-
-        if (options.Skip > 0)
         {
-            sql.Append($" OFFSET {options.Skip}");
+            var limit = options.Take > 0 ? options.Take : ItemLoadCount;
+            sql.Append($" LIMIT {limit}");
+
+            if (options.Skip > 0)
+            {
+                sql.Append($" OFFSET {options.Skip}");
+            }
         }
 
         return (sql.ToString(), parameters.ToArray());
     }
 
-    private static List<MailCopy> ApplyOptionsToPreFetchedMails(MailListInitializationOptions options)
+    private static List<MailCopy> ApplyOptionsToPreFetchedMails(MailListInitializationOptions options, bool pinnedOnly = false)
     {
         var allowedFolderIds = options.Folders.Select(f => f.Id).ToHashSet();
         var accountIdsByFolderId = options.Folders
@@ -287,6 +295,11 @@ public class MailService : BaseDatabaseService, IMailService
             query = query.Where(m => !options.ExistingUniqueIds.ContainsKey(m.UniqueId));
         }
 
+        if (pinnedOnly)
+        {
+            query = query.Where(m => m.IsPinned);
+        }
+
         query = options.DeduplicateByServerId
             ? query
                 .GroupBy(m => (ResolveMailAccountId(m, accountIdsByFolderId), ResolveServerMailId(m)))
@@ -302,16 +315,21 @@ public class MailService : BaseDatabaseService, IMailService
 
         query = options.SortingOptionType switch
         {
-            SortingOptionType.Sender => query.OrderBy(m => m.FromName).ThenByDescending(m => m.CreationDate),
+            SortingOptionType.Sender => query
-            _ => query.OrderByDescending(m => m.CreationDate)
+                .OrderByDescending(m => m.IsPinned)
+                .ThenBy(m => m.FromName)
+                .ThenByDescending(m => m.CreationDate),
+            _ => query
+                .OrderByDescending(m => m.IsPinned)
+                .ThenByDescending(m => m.CreationDate)
         };
 
-        if (options.Skip > 0)
+        if (!pinnedOnly && options.Skip > 0)
         {
             query = query.Skip(options.Skip);
         }
 
-        if (options.Take > 0)
+        if (!pinnedOnly && options.Take > 0)
         {
             query = query.Take(options.Take);
         }
@@ -333,17 +351,23 @@ public class MailService : BaseDatabaseService, IMailService
     private static string ResolveServerMailId(MailCopy mail)
         => string.IsNullOrWhiteSpace(mail?.Id) ? mail?.UniqueId.ToString("N") ?? string.Empty : mail.Id;
 
-    public async Task<List<MailCopy>> FetchMailsAsync(MailListInitializationOptions options, CancellationToken cancellationToken = default)
+    public Task<List<MailCopy>> FetchMailsAsync(MailListInitializationOptions options, CancellationToken cancellationToken = default)
+        => FetchMailsInternalAsync(options, pinnedOnly: false, cancellationToken);
+
+    public Task<List<MailCopy>> FetchPinnedMailsAsync(MailListInitializationOptions options, CancellationToken cancellationToken = default)
+        => FetchMailsInternalAsync(options, pinnedOnly: true, cancellationToken);
+
+    private async Task<List<MailCopy>> FetchMailsInternalAsync(MailListInitializationOptions options, bool pinnedOnly, CancellationToken cancellationToken = default)
     {
         List<MailCopy> mails;
 
         if (options.PreFetchMailCopies != null && !options.IsCategoryView)
         {
-            mails = ApplyOptionsToPreFetchedMails(options);
+            mails = ApplyOptionsToPreFetchedMails(options, pinnedOnly);
         }
         else
         {
-            var (query, parameters) = BuildMailFetchQuery(options);
+            var (query, parameters) = BuildMailFetchQuery(options, pinnedOnly);
             mails = await Connection.QueryAsync<MailCopy>(query, parameters);
         }
 
@@ -735,7 +759,8 @@ public class MailService : BaseDatabaseService, IMailService
 
         await Connection.InsertAsync(mailCopy, typeof(MailCopy)).ConfigureAwait(false);
 
-        ReportUIChange(new MailAddedMessage(mailCopy, EntityUpdateSource.Server));
+        var hydratedMailCopy = await HydrateMailCopyAsync(mailCopy).ConfigureAwait(false);
+        ReportUIChange(new MailAddedMessage(hydratedMailCopy, EntityUpdateSource.Server));
     }
 
     public async Task UpdateMailAsync(MailCopy mailCopy)
@@ -749,9 +774,20 @@ public class MailService : BaseDatabaseService, IMailService
 
         _logger.Debug("Updating mail {MailCopyId} with Folder {FolderId}", mailCopy.Id, mailCopy.FolderId);
 
+        var existingMailCopy = mailCopy.UniqueId != Guid.Empty
+            ? await Connection.FindAsync<MailCopy>(mailCopy.UniqueId).ConfigureAwait(false)
+            : null;
+
+        if (existingMailCopy != null)
+        {
+            // Pinning is managed locally for now, so server refreshes should not clear it.
+            mailCopy.IsPinned = existingMailCopy.IsPinned;
+        }
+
         await Connection.UpdateAsync(mailCopy, typeof(MailCopy)).ConfigureAwait(false);
 
-        ReportUIChange(new MailUpdatedMessage(mailCopy, EntityUpdateSource.Server));
+        var hydratedMailCopy = await HydrateMailCopyAsync(mailCopy).ConfigureAwait(false);
+        ReportUIChange(new MailUpdatedMessage(hydratedMailCopy, EntityUpdateSource.Server));
     }
 
     private async Task DeleteMailInternalAsync(MailCopy mailCopy, bool preserveMimeFile)
@@ -807,12 +843,23 @@ public class MailService : BaseDatabaseService, IMailService
             WeakReferenceMessenger.Default.Send(new BulkMailReadStatusChanged(readMailUniqueIds));
         }
 
+        var hydratedUpdatesByUniqueId = (await HydrateMailCopiesAsync(
+                pendingUpdates
+                    .Where(x => x.MailCopy != null)
+                    .Select(x => x.MailCopy)
+                    .GroupBy(x => x.UniqueId)
+                    .Select(group => group.First())
+                    .ToList())
+            .ConfigureAwait(false))
+            .Where(x => x != null)
+            .ToDictionary(x => x.UniqueId);
+
         foreach (var updateGroup in pendingUpdates
                      .Where(x => x.MailCopy != null)
                      .GroupBy(x => x.ChangedProperties))
         {
             var updatedMails = updateGroup
-                .Select(x => x.MailCopy)
+                .Select(x => hydratedUpdatesByUniqueId.GetValueOrDefault(x.MailCopy.UniqueId, x.MailCopy))
                 .Where(x => x != null)
                 .ToList();
 
@@ -875,6 +922,41 @@ public class MailService : BaseDatabaseService, IMailService
             return MailCopyChangeFlags.IsFlagged;
         });
 
+    public async Task ChangePinnedStatusAsync(IEnumerable<Guid> uniqueMailIds, bool isPinned)
+    {
+        var distinctUniqueIds = uniqueMailIds?
+            .Where(id => id != Guid.Empty)
+            .Distinct()
+            .ToList() ?? [];
+
+        if (distinctUniqueIds.Count == 0)
+            return;
+
+        var placeholders = string.Join(",", distinctUniqueIds.Select(_ => "?"));
+        var mailCopies = await Connection
+            .QueryAsync<MailCopy>($"SELECT * FROM MailCopy WHERE UniqueId IN ({placeholders})", distinctUniqueIds.Cast<object>().ToArray())
+            .ConfigureAwait(false);
+
+        if (mailCopies.Count == 0)
+        {
+            _logger.Warning("Changing pin status failed because there are no matching copies for {MailCopyCount} unique ids.", distinctUniqueIds.Count);
+            return;
+        }
+
+        var pendingUpdates = new List<(MailCopy MailCopy, MailCopyChangeFlags ChangedProperties)>();
+
+        foreach (var mailCopy in mailCopies)
+        {
+            if (mailCopy.IsPinned == isPinned)
+                continue;
+
+            mailCopy.IsPinned = isPinned;
+            pendingUpdates.Add((mailCopy, MailCopyChangeFlags.IsPinned));
+        }
+
+        await PersistMailCopyUpdatesAsync(pendingUpdates).ConfigureAwait(false);
+    }
+
     public async Task ApplyMailStateUpdatesAsync(IEnumerable<MailCopyStateUpdate> updates)
     {
         var updateLookup = new Dictionary<string, MailCopyStateUpdate>(StringComparer.Ordinal);

Wino.Services/SpecialImapProviderConfigResolver.cs

@@ -14,6 +14,8 @@ public class SpecialImapProviderConfigResolver : ISpecialImapProviderConfigResol
 
         if (details.SpecialImapProvider == SpecialImapProvider.iCloud)
         {
+            var iCloudMailboxUsername = GetICloudMailboxUsername(details.Address);
+
             resolvedConfig = new CustomServerInformation()
             {
                 IncomingServer = "imap.mail.me.com",
@@ -29,9 +31,9 @@ public class SpecialImapProviderConfigResolver : ISpecialImapProviderConfigResol
                 CalDavServiceUrl = "https://caldav.icloud.com/"
             };
 
-            // iCloud takes username before the @icloud part for incoming, but full address as outgoing.
+            // iCloud IMAP/SMTP authentication uses only the local-part mailbox username.
-            resolvedConfig.IncomingServerUsername = details.Address.Split('@')[0];
+            resolvedConfig.IncomingServerUsername = iCloudMailboxUsername;
-            resolvedConfig.OutgoingServerUsername = details.Address;
+            resolvedConfig.OutgoingServerUsername = iCloudMailboxUsername;
         }
         else if (details.SpecialImapProvider == SpecialImapProvider.Yahoo)
         {
@@ -73,4 +75,17 @@ public class SpecialImapProviderConfigResolver : ISpecialImapProviderConfigResol
 
         return resolvedConfig;
     }
+
+    private static string GetICloudMailboxUsername(string address)
+    {
+        if (string.IsNullOrWhiteSpace(address))
+            return string.Empty;
+
+        var normalizedAddress = address.Trim();
+        var atIndex = normalizedAddress.IndexOf('@');
+
+        return atIndex > 0
+            ? normalizedAddress[..atIndex]
+            : normalizedAddress;
+    }
 }