Add configurable thread item sorting

Wino.Core.Domain/Interfaces/IPreferencesService.cs

@@ -132,6 +132,11 @@ public interface IPreferencesService : INotifyPropertyChanged
     /// </summary>
     bool IsThreadingEnabled { get; set; }
 
+    /// <summary>
+    /// Setting: Whether the newest message in a conversation should appear first.
+    /// </summary>
+    bool IsNewestThreadMailFirst { get; set; }
+
     /// <summary>
     /// Setting: Show sender pictures in mail list.
     /// </summary>

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

@@ -1074,6 +1074,12 @@
     "SettingsTaskbarBadge_Title": "Taskbar Badge",
     "SettingsThreads_Description": "Organize messages into conversation threads.",
     "SettingsThreads_Title": "Conversation Threading",
+    "SettingsThreads_Enabled_Description": "Group related messages into a single conversation.",
+    "SettingsThreads_Enabled_Title": "Enable conversation threading",
+    "SettingsThreadOrder_Description": "Choose how items are ordered inside a conversation thread.",
+    "SettingsThreadOrder_Title": "Thread item sorting",
+    "SettingsThreadOrder_LastItemFirst": "Last item first",
+    "SettingsThreadOrder_FirstItemFirst": "First item first",
     "SettingsUnlinkAccounts_Description": "Remove the link between accounts. his will not delete your accounts.",
     "SettingsUnlinkAccounts_Title": "Unlink Accounts",
     "SettingsMailRendering_ActionLabels_Title": "Action labels",

Wino.Mail.ViewModels/Collections/WinoMailCollection.cs

@@ -39,6 +39,7 @@ public class WinoMailCollection : ObservableRecipient, IRecipient<SelectedItemsC
 
     public event EventHandler<MailItemViewModel> MailItemRemoved;
     public event EventHandler ItemSelectionChanged;
+    public Func<string, ThreadMailItemViewModel> ThreadItemFactory { get; set; } = static threadId => new ThreadMailItemViewModel(threadId, true);
 
     private ListItemComparer listComparer = new();
 
@@ -457,7 +458,7 @@ public class WinoMailCollection : ObservableRecipient, IRecipient<SelectedItemsC
 
     private async Task CreateNewThreadAsync(ObservableGroup<object, IMailListItem> group, MailItemViewModel item, MailCopy addedItem)
     {
-        var threadViewModel = new ThreadMailItemViewModel(item.MailCopy.ThreadId);
+        var threadViewModel = ThreadItemFactory(item.MailCopy.ThreadId);
 
         await ExecuteUIThread(() =>
         {
@@ -710,7 +711,7 @@ public class WinoMailCollection : ObservableRecipient, IRecipient<SelectedItemsC
                 if (batchThreadLookup.TryGetValue(item.MailCopy.ThreadId, out var threadableItems) && threadableItems.Count > 1)
                 {
                     // Create a new thread with all matching items - defer UI operations
-                    var threadViewModel = new ThreadMailItemViewModel(item.MailCopy.ThreadId);
+                    var threadViewModel = ThreadItemFactory(item.MailCopy.ThreadId);
 
                     // Add emails without UI thread for now
                     foreach (var threadItem in threadableItems)

Wino.Mail.ViewModels/Data/ThreadMailItemViewModel.cs

@@ -17,8 +17,9 @@ namespace Wino.Mail.ViewModels.Data;
 public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListItem, IMailItemDisplayInformation
 {
     private readonly string _threadId;
+    private readonly bool _isNewestEmailFirst;
     private readonly HashSet<Guid> _uniqueIdSet = [];
-    private MailItemViewModel _cachedLatestMailViewModel;
+    private MailItemViewModel _cachedNewestMailViewModel;
     private int _suspendChildPropertyNotificationsCount;
 
     [ObservableProperty]
@@ -53,27 +54,27 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     /// <summary>
     /// Gets the latest email's subject for display
     /// </summary>
-    public string Subject => latestMailViewModel?.MailCopy?.Subject;
+    public string Subject => newestMailViewModel?.MailCopy?.Subject;
 
     /// <summary>
     /// Gets the latest email's sender name for display
     /// </summary>
-    public string FromName => latestMailViewModel?.MailCopy?.FromName ?? Translator.UnknownSender;
+    public string FromName => newestMailViewModel?.MailCopy?.FromName ?? Translator.UnknownSender;
 
     /// <summary>
     /// Gets the latest email's creation date for sorting
     /// </summary>
-    public DateTime CreationDate => latestMailViewModel?.MailCopy?.CreationDate ?? DateTime.MinValue;
+    public DateTime CreationDate => newestMailViewModel?.MailCopy?.CreationDate ?? DateTime.MinValue;
 
     /// <summary>
     /// Gets the latest email's sender address for display
     /// </summary>
-    public string FromAddress => latestMailViewModel?.FromAddress ?? string.Empty;
+    public string FromAddress => newestMailViewModel?.FromAddress ?? string.Empty;
 
     /// <summary>
     /// Gets the preview text from the latest email
     /// </summary>
-    public string PreviewText => latestMailViewModel?.PreviewText ?? string.Empty;
+    public string PreviewText => newestMailViewModel?.PreviewText ?? string.Empty;
 
     /// <summary>
     /// Gets whether any email in this thread has attachments
@@ -93,18 +94,18 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     /// <summary>
     /// Gets whether the latest email is focused
     /// </summary>
-    public bool IsFocused => latestMailViewModel?.IsFocused ?? false;
+    public bool IsFocused => newestMailViewModel?.IsFocused ?? false;
 
     /// <summary>
     /// Gets whether all emails in this thread are read
     /// </summary>
     public bool IsRead => ThreadEmails.All(e => e.IsRead);
 
-    public bool HasReadReceiptTracking => latestMailViewModel?.HasReadReceiptTracking ?? false;
+    public bool HasReadReceiptTracking => newestMailViewModel?.HasReadReceiptTracking ?? false;
 
-    public bool IsReadReceiptAcknowledged => latestMailViewModel?.IsReadReceiptAcknowledged ?? false;
+    public bool IsReadReceiptAcknowledged => newestMailViewModel?.IsReadReceiptAcknowledged ?? false;
 
-    public string ReadReceiptDisplayText => latestMailViewModel?.ReadReceiptDisplayText ?? string.Empty;
+    public string ReadReceiptDisplayText => newestMailViewModel?.ReadReceiptDisplayText ?? string.Empty;
 
     /// <summary>
     /// Gets whether any email in this thread is a draft
@@ -114,58 +115,58 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     /// <summary>
     /// Gets the draft ID from the latest email if it's a draft
     /// </summary>
-    public string DraftId => latestMailViewModel?.DraftId ?? string.Empty;
+    public string DraftId => newestMailViewModel?.DraftId ?? string.Empty;
 
     /// <summary>
     /// Gets the ID from the latest email
     /// </summary>
-    public string Id => latestMailViewModel?.Id ?? string.Empty;
+    public string Id => newestMailViewModel?.Id ?? string.Empty;
 
     /// <summary>
     /// Gets the importance of the latest email
     /// </summary>
-    public MailImportance Importance => latestMailViewModel?.Importance ?? MailImportance.Normal;
+    public MailImportance Importance => newestMailViewModel?.Importance ?? MailImportance.Normal;
 
     /// <summary>
     /// Gets the thread ID from the latest email
     /// </summary>
-    public string ThreadId => latestMailViewModel?.ThreadId ?? _threadId;
+    public string ThreadId => newestMailViewModel?.ThreadId ?? _threadId;
 
     /// <summary>
     /// Gets the message ID from the latest email
     /// </summary>
-    public string MessageId => latestMailViewModel?.MessageId ?? string.Empty;
+    public string MessageId => newestMailViewModel?.MessageId ?? string.Empty;
 
     /// <summary>
     /// Gets the references from the latest email
     /// </summary>
-    public string References => latestMailViewModel?.References ?? string.Empty;
+    public string References => newestMailViewModel?.References ?? string.Empty;
 
     /// <summary>
     /// Gets the in-reply-to from the latest email
     /// </summary>
-    public string InReplyTo => latestMailViewModel?.InReplyTo ?? string.Empty;
+    public string InReplyTo => newestMailViewModel?.InReplyTo ?? string.Empty;
 
     /// <summary>
     /// Gets the file ID from the latest email
     /// </summary>
-    public Guid FileId => latestMailViewModel?.FileId ?? Guid.Empty;
+    public Guid FileId => newestMailViewModel?.FileId ?? Guid.Empty;
 
     /// <summary>
     /// Gets the folder ID from the latest email
     /// </summary>
-    public Guid FolderId => latestMailViewModel?.FolderId ?? Guid.Empty;
+    public Guid FolderId => newestMailViewModel?.FolderId ?? Guid.Empty;
 
     /// <summary>
     /// Gets the unique ID from the latest email
     /// </summary>
-    public Guid UniqueId => latestMailViewModel?.UniqueId ?? Guid.Empty;
+    public Guid UniqueId => newestMailViewModel?.UniqueId ?? Guid.Empty;
 
-    public Guid? ContactPictureFileId => latestMailViewModel?.MailCopy?.SenderContact?.ContactPictureFileId;
+    public Guid? ContactPictureFileId => newestMailViewModel?.MailCopy?.SenderContact?.ContactPictureFileId;
 
-    public bool ThumbnailUpdatedEvent => latestMailViewModel?.ThumbnailUpdatedEvent ?? false;
+    public bool ThumbnailUpdatedEvent => newestMailViewModel?.ThumbnailUpdatedEvent ?? false;
 
-    public AccountContact SenderContact => latestMailViewModel?.MailCopy?.SenderContact;
+    public AccountContact SenderContact => newestMailViewModel?.MailCopy?.SenderContact;
 
     /// <summary>
     /// Gets all emails in this thread (observable)
@@ -201,15 +202,16 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
     [NotifyPropertyChangedFor(nameof(SenderContact))]
     public partial ObservableCollection<MailItemViewModel> ThreadEmails { get; set; } = [];
 
-    private MailItemViewModel latestMailViewModel => _cachedLatestMailViewModel;
+    private MailItemViewModel newestMailViewModel => _cachedNewestMailViewModel;
 
     public DateTime SortingDate => CreationDate;
 
     public string SortingName => FromName;
 
-    public ThreadMailItemViewModel(string threadId)
+    public ThreadMailItemViewModel(string threadId, bool isNewestEmailFirst)
     {
         _threadId = threadId;
+        _isNewestEmailFirst = isNewestEmailFirst;
     }
 
     internal void SuspendChildPropertyNotifications() => _suspendChildPropertyNotificationsCount++;
@@ -224,11 +226,21 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
 
     private void RefreshLatestMailCache()
     {
-        _cachedLatestMailViewModel = ThreadEmails
+        _cachedNewestMailViewModel = ThreadEmails
             .OrderByDescending(static item => item.MailCopy.CreationDate)
             .FirstOrDefault();
     }
 
+    public MailItemViewModel GetDefaultSelectedThreadEmail()
+    {
+        if (ThreadEmails.Count == 0)
+        {
+            return null;
+        }
+
+        return _isNewestEmailFirst ? ThreadEmails.FirstOrDefault() : ThreadEmails.LastOrDefault();
+    }
+
     /// <summary>
     /// Adds an email to this thread
     /// </summary>
@@ -237,11 +249,15 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
         if (email.MailCopy.ThreadId != _threadId)
             throw new ArgumentException($"Email ThreadId '{email.MailCopy.ThreadId}' does not match expander ThreadId '{_threadId}'");
 
-        // Insert email in sorted order by CreationDate (newest first, oldest last)
+        // Insert email in sorted order by CreationDate based on the configured thread direction.
         var insertIndex = 0;
         for (int i = 0; i < ThreadEmails.Count; i++)
         {
-            if (ThreadEmails[i].MailCopy.CreationDate < email.MailCopy.CreationDate)
+            bool shouldInsertBefore = _isNewestEmailFirst
+                ? ThreadEmails[i].MailCopy.CreationDate < email.MailCopy.CreationDate
+                : ThreadEmails[i].MailCopy.CreationDate > email.MailCopy.CreationDate;
+
+            if (shouldInsertBefore)
             {
                 insertIndex = i;
                 break;
@@ -298,7 +314,7 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
 
         if (e.PropertyName == nameof(MailItemViewModel.ThumbnailUpdatedEvent))
         {
-            if (ReferenceEquals(updatedMailItem, latestMailViewModel))
+            if (ReferenceEquals(updatedMailItem, newestMailViewModel))
             {
                 OnPropertyChanged(nameof(ThumbnailUpdatedEvent));
             }
@@ -329,7 +345,7 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
         if (changedFlags == MailCopyChangeFlags.None)
             return;
 
-        var previousLatest = latestMailViewModel;
+        var previousLatest = newestMailViewModel;
 
         if (changedFlags == MailCopyChangeFlags.All ||
             (changedFlags & MailCopyChangeFlags.CreationDate) != 0 ||
@@ -339,7 +355,7 @@ public partial class ThreadMailItemViewModel : ObservableRecipient, IMailListIte
             RefreshLatestMailCache();
         }
 
-        var currentLatest = latestMailViewModel;
+        var currentLatest = newestMailViewModel;
         var latestChanged = !ReferenceEquals(previousLatest, currentLatest);
 
         var updatesDisplayedLatest = changedFlags == MailCopyChangeFlags.All ||

Wino.Mail.ViewModels/MailListPageViewModel.cs

@@ -205,6 +205,7 @@ public partial class MailListPageViewModel : MailBaseViewModel,
 
         SelectedFilterOption = FilterOptions[0];
         SelectedSortingOption = SortingOptions[0];
+        MailCollection.ThreadItemFactory = threadId => new ThreadMailItemViewModel(threadId, PreferencesService.IsNewestThreadMailFirst);
 
         MailListLength = statePersistenceService.MailListPaneLength;
     }

Wino.Mail.ViewModels/MessageListPageViewModel.cs

@@ -42,6 +42,12 @@ public partial class MessageListPageViewModel : MailBaseViewModel
         Translator.HoverActionOption_MoveJunk
     ];
 
+    public List<string> ThreadItemSortingOptions { get; } =
+    [
+        Translator.SettingsThreadOrder_LastItemFirst,
+        Translator.SettingsThreadOrder_FirstItemFirst
+    ];
+
     public IMailItemDisplayInformation DemoPreviewMailItemInformation { get; } = new DemoMailItemDisplayInformation();
 
     public MailListDisplayMode SelectedMailSpacingMode => availableMailSpacingOptions[selectedMailSpacingIndex];
@@ -73,6 +79,19 @@ public partial class MessageListPageViewModel : MailBaseViewModel
         }
     }
 
+    private int selectedThreadItemSortingIndex;
+    public int SelectedThreadItemSortingIndex
+    {
+        get => selectedThreadItemSortingIndex;
+        set
+        {
+            if (SetProperty(ref selectedThreadItemSortingIndex, value) && value >= 0)
+            {
+                PreferencesService.IsNewestThreadMailFirst = value == 0;
+            }
+        }
+    }
+
     #region Properties
     private int leftHoverActionIndex;
     public int LeftHoverActionIndex
@@ -128,6 +147,7 @@ public partial class MessageListPageViewModel : MailBaseViewModel
         rightHoverActionIndex = availableHoverActions.IndexOf(PreferencesService.RightHoverAction);
         selectedMailSpacingIndex = availableMailSpacingOptions.IndexOf(PreferencesService.MailItemDisplayMode);
         SelectedMarkAsOptionIndex = Array.IndexOf(Enum.GetValues<MailMarkAsOption>(), PreferencesService.MarkAsPreference);
+        selectedThreadItemSortingIndex = PreferencesService.IsNewestThreadMailFirst ? 0 : 1;
     }
 
     [RelayCommand]

Wino.Mail.WinUI/Services/PreferencesService.cs

@@ -117,6 +117,12 @@ public class PreferencesService(IConfigurationService configurationService) : Ob
         set => SetPropertyAndSave(nameof(IsThreadingEnabled), value);
     }
 
+    public bool IsNewestThreadMailFirst
+    {
+        get => _configurationService.Get(nameof(IsNewestThreadMailFirst), true);
+        set => SetPropertyAndSave(nameof(IsNewestThreadMailFirst), value);
+    }
+
     public bool IsMailListActionBarEnabled
     {
         get => _configurationService.Get(nameof(IsMailListActionBarEnabled), false);

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

@@ -990,10 +990,10 @@ public sealed partial class MailListPage : MailListPageAbstract,
                 }
                 else
                 {
-                    var firstChild = clickedThread.ThreadEmails.FirstOrDefault();
+                    var defaultSelectedChild = clickedThread.GetDefaultSelectedThreadEmail();
-                    if (firstChild != null)
+                    if (defaultSelectedChild != null)
                     {
-                        firstChild.IsSelected = true;
+                        defaultSelectedChild.IsSelected = true;
                     }
                 }