diff --git a/Codev.Avalonia.Tests/MainWindowTests.cs b/Codev.Avalonia.Tests/MainWindowTests.cs
index 3745f2b3..dc734119 100644
--- a/Codev.Avalonia.Tests/MainWindowTests.cs
+++ b/Codev.Avalonia.Tests/MainWindowTests.cs
@@ -455,6 +455,11 @@ public async Task Sidebar_conversation_sections_toggle_and_persist_expanded_stat
             viewModel.NewConversationCommand.Execute(null);
             var recent = Assert.IsType<Conversation>(viewModel.ActiveConversation);
             recent.Title = "Recent sidebar fixture";
+            viewModel.NewConversationCommand.Execute(null);
+            var later = Assert.IsType<Conversation>(viewModel.ActiveConversation);
+            later.Title = "Second recent sidebar fixture";
+            Assert.True(viewModel.ReorderConversation(recent.Id, later, insertAfter: false));
+            Assert.Equal(new[] { recent.Id, later.Id }, viewModel.RecentConversations.Select(item => item.Id));
 
             var pinnedToggle = Assert.IsType<Button>(window.FindControl<Button>("PinnedConversationsToggleButton"));
             var pinnedList = Assert.IsType<ItemsControl>(window.FindControl<ItemsControl>("PinnedConversationsList"));
@@ -462,6 +467,11 @@ public async Task Sidebar_conversation_sections_toggle_and_persist_expanded_stat
             var recentList = Assert.IsType<ItemsControl>(window.FindControl<ItemsControl>("RecentConversationsList"));
             Assert.True(pinnedList.IsVisible);
             Assert.True(recentList.IsVisible);
+            Assert.All(window.GetVisualDescendants().OfType<Button>().Where(button => button.DataContext is Conversation), button =>
+            {
+                Assert.True(DragDrop.GetAllowDrop(button));
+                Assert.Equal("Drag to reorder within this section", ToolTip.GetTip(button));
+            });
 
             await Dispatcher.UIThread.InvokeAsync(() => pinnedToggle.RaiseEvent(new RoutedEventArgs(Button.ClickEvent)));
             await Dispatcher.UIThread.InvokeAsync(() => recentToggle.RaiseEvent(new RoutedEventArgs(Button.ClickEvent)));
@@ -487,6 +497,7 @@ public async Task Sidebar_conversation_sections_toggle_and_persist_expanded_stat
             var reloadedPinned = Assert.Single(reloadedViewModel.PinnedConversations);
             Assert.Equal(pinnedConversationId, reloadedPinned.Id);
             Assert.Equal("Pinned sidebar fixture", reloadedPinned.Title);
+            Assert.Equal(new[] { recent.Id, later.Id }, reloadedViewModel.RecentConversations.Select(item => item.Id));
             Assert.DoesNotContain(reloadedViewModel.RecentConversations, conversation => conversation.Id == pinnedConversationId);
         }
         finally
diff --git a/Codev.Avalonia/ViewModels/MainViewModel.cs b/Codev.Avalonia/ViewModels/MainViewModel.cs
index 0b9fee27..6b19b8a8 100644
--- a/Codev.Avalonia/ViewModels/MainViewModel.cs
+++ b/Codev.Avalonia/ViewModels/MainViewModel.cs
@@ -266,7 +266,7 @@ public MainViewModel(string? localDataRoot = null, HttpMessageHandler? httpMessa
         LoadConversations();
         if (_conversations.Count == 0)
         {
-            _conversations.Add(new Codev.Conversation { Title = "New conversation", UpdatedAt = DateTimeOffset.Now });
+            _conversations.Add(new Codev.Conversation { Title = "New conversation", UpdatedAt = DateTimeOffset.Now, SidebarOrder = 0 });
             Persist();
         }
         RebuildLists();
@@ -1519,7 +1519,8 @@ public void NewConversation()
             ThinkEnabled = ThinkEnabled,
             IncludeRepoMap = IncludeRepoMap,
             NumCtx = ContextSize,
-            UpdatedAt = DateTimeOffset.Now
+            UpdatedAt = DateTimeOffset.Now,
+            SidebarOrder = NextSidebarOrder(isPinned: false, isArchived: false)
         };
         _conversations.Insert(0, conversation);
         SelectConversation(conversation);
@@ -1552,6 +1553,7 @@ public async Task<bool> ForkConversationAsync(Codev.Conversation conversation)
         try
         {
             var fork = await Codev.ConversationForkService.CreateForkAsync(conversation);
+            fork.SidebarOrder = NextSidebarOrder(fork.IsPinned, fork.IsArchived);
             _conversations.Insert(0, fork);
             SelectConversation(fork);
             RebuildLists();
@@ -1577,6 +1579,7 @@ public bool ToggleConversationArchive(Codev.Conversation conversation)
         }
 
         conversation.IsArchived = !conversation.IsArchived;
+        if (!conversation.IsArchived) conversation.SidebarOrder = NextSidebarOrder(conversation.IsPinned, isArchived: false);
         conversation.UpdatedAt = DateTimeOffset.Now;
         if (ReferenceEquals(ActiveConversation, conversation))
         {
@@ -1593,6 +1596,22 @@ public bool ToggleConversationArchive(Codev.Conversation conversation)
         return true;
     }
 
+    public bool ReorderConversation(Guid draggedId, Codev.Conversation target, bool insertAfter)
+    {
+        var dragged = _conversations.FirstOrDefault(item => item.Id == draggedId);
+        if (dragged is null || !_conversations.Contains(target) || dragged.IsPinned != target.IsPinned ||
+            dragged.IsArchived != target.IsArchived || dragged.ParentConversationId is not null || target.ParentConversationId is not null) return false;
+
+        var section = _conversations.Where(item => item.ParentConversationId is null &&
+            item.IsPinned == dragged.IsPinned && item.IsArchived == dragged.IsArchived)
+            .OrderBy(item => item.SidebarOrder ?? int.MaxValue)
+            .ThenByDescending(item => item.UpdatedAt).ToList();
+        if (!Codev.ConversationSidebarOrdering.TryMove(section, dragged.Id, target.Id, insertAfter)) return false;
+        Persist();
+        RebuildLists();
+        return true;
+    }
+
     public async Task<bool> DeleteConversationAsync(Codev.Conversation conversation)
     {
         if (!_conversations.Contains(conversation)) return false;
@@ -2404,6 +2423,8 @@ public async Task<int> ImportConversationBackupAsync(string json)
         foreach (var conversation in imported.OrderBy(item => item.UpdatedAt))
         {
             conversation.IsArchived = false;
+            if (conversation.ParentConversationId is null)
+                conversation.SidebarOrder = NextSidebarOrder(conversation.IsPinned, isArchived: false);
             if (!string.IsNullOrWhiteSpace(conversation.ProjectPath) && !Directory.Exists(conversation.ProjectPath))
                 conversation.ProjectPath = null;
             _conversations.Insert(0, conversation);
@@ -2782,6 +2803,7 @@ private void TogglePin()
     {
         if (ActiveConversation is not { } conversation) return;
         conversation.IsPinned = !conversation.IsPinned;
+        conversation.SidebarOrder = NextSidebarOrder(conversation.IsPinned, conversation.IsArchived);
         conversation.UpdatedAt = DateTimeOffset.Now;
         OnPropertyChanged(nameof(PinLabel));
         Persist();
@@ -4393,6 +4415,7 @@ public async Task<bool> OpenSideChatFromMessageAsync(Codev.ChatMessage message)
         try
         {
             var sideChat = await Codev.ConversationForkService.CreateSideChatAsync(source, message.MessageIndex);
+            sideChat.SidebarOrder = NextSidebarOrder(sideChat.IsPinned, sideChat.IsArchived);
             _conversations.Insert(0, sideChat);
             SelectConversation(sideChat);
             RebuildLists();
@@ -5004,8 +5027,8 @@ private void RebuildLists()
                 conversation.IsArchived == _showArchived &&
                 (matchedIds.Contains(conversation.Id) || conversation.ChildConversations.Any(child => matchedIds.Contains(child.Id))))
             .OrderByDescending(conversation => conversation.UpdatedAt).ToArray();
-        Reset(PinnedConversations, visible.Where(c => c.IsPinned));
-        Reset(RecentConversations, visible.Where(c => !c.IsPinned));
+        Reset(PinnedConversations, visible.Where(c => c.IsPinned).OrderBy(c => c.SidebarOrder ?? int.MaxValue).ThenByDescending(c => c.UpdatedAt));
+        Reset(RecentConversations, visible.Where(c => !c.IsPinned).OrderBy(c => c.SidebarOrder ?? int.MaxValue).ThenByDescending(c => c.UpdatedAt));
         OnPropertyChanged(nameof(PinnedConversationsSectionLabel));
         OnPropertyChanged(nameof(RecentConversationsSectionLabel));
         OnPropertyChanged(nameof(ConversationTitle));
@@ -5063,6 +5086,12 @@ private static void Reset<T>(ObservableCollection<T> target, IEnumerable<T> sour
         foreach (var item in source) target.Add(item);
     }
 
+    private int NextSidebarOrder(bool isPinned, bool isArchived) => _conversations
+        .Where(item => item.ParentConversationId is null && item.IsPinned == isPinned && item.IsArchived == isArchived)
+        .Select(item => item.SidebarOrder ?? int.MaxValue)
+        .DefaultIfEmpty(0)
+        .Min() - 1;
+
     private void LoadConversations()
     {
         try
diff --git a/Codev.Avalonia/Views/MainWindow.axaml b/Codev.Avalonia/Views/MainWindow.axaml
index fb6f977e..1203d5d4 100644
--- a/Codev.Avalonia/Views/MainWindow.axaml
+++ b/Codev.Avalonia/Views/MainWindow.axaml
@@ -104,7 +104,7 @@
                         <ItemsControl x:Name="PinnedConversationsList" ItemsSource="{Binding PinnedConversations}" IsVisible="{Binding PinnedConversationsExpanded}">
                             <ItemsControl.ItemTemplate><DataTemplate x:DataType="core:Conversation">
                                 <StackPanel>
-                                    <Button Classes="nav" Content="{Binding Title}" Command="{Binding $parent[Window].DataContext.SelectConversationCommand}" CommandParameter="{Binding}">
+                                    <Button Classes="nav" Content="{Binding Title}" ToolTip.Tip="Drag to reorder within this section" Command="{Binding $parent[Window].DataContext.SelectConversationCommand}" CommandParameter="{Binding}" PointerPressed="Conversation_PointerPressed" DragDrop.AllowDrop="True" DragDrop.DragOver="Conversation_DragOver" DragDrop.Drop="Conversation_Drop">
                                         <Button.ContextMenu>
                                             <ContextMenu>
                                                 <MenuItem Header="Fork conversation" Tag="{Binding}" Click="ForkConversation_Click" />
@@ -137,7 +137,7 @@
                         <ItemsControl x:Name="RecentConversationsList" ItemsSource="{Binding RecentConversations}" IsVisible="{Binding RecentConversationsExpanded}">
                             <ItemsControl.ItemTemplate><DataTemplate x:DataType="core:Conversation">
                                 <StackPanel>
-                                    <Button Classes="nav" Content="{Binding Title}" Command="{Binding $parent[Window].DataContext.SelectConversationCommand}" CommandParameter="{Binding}">
+                                    <Button Classes="nav" Content="{Binding Title}" ToolTip.Tip="Drag to reorder within this section" Command="{Binding $parent[Window].DataContext.SelectConversationCommand}" CommandParameter="{Binding}" PointerPressed="Conversation_PointerPressed" DragDrop.AllowDrop="True" DragDrop.DragOver="Conversation_DragOver" DragDrop.Drop="Conversation_Drop">
                                         <Button.ContextMenu>
                                             <ContextMenu>
                                                 <MenuItem Header="Fork conversation" Tag="{Binding}" Click="ForkConversation_Click" />
diff --git a/Codev.Avalonia/Views/MainWindow.axaml.cs b/Codev.Avalonia/Views/MainWindow.axaml.cs
index 2797c0e2..363ba823 100644
--- a/Codev.Avalonia/Views/MainWindow.axaml.cs
+++ b/Codev.Avalonia/Views/MainWindow.axaml.cs
@@ -15,6 +15,7 @@ namespace Codev.Avalonia.Views;
 
 public partial class MainWindow : Window
 {
+    private static readonly DataFormat<string> ConversationDragFormat = DataFormat.CreateStringApplicationFormat("Codev.ConversationId");
     private INotifyCollectionChanged? _observedMessages;
     private bool _followOutput = true;
     private bool _scrollPending;
@@ -149,6 +150,32 @@ private void Composer_Drop(object? sender, DragEventArgs e)
         viewModel.AddContextFiles(paths);
     }
 
+    private async void Conversation_PointerPressed(object? sender, PointerPressedEventArgs e)
+    {
+        if (sender is not Button { DataContext: Codev.Conversation conversation } button ||
+            !e.GetCurrentPoint(button).Properties.IsLeftButtonPressed) return;
+
+        var transfer = new DataTransfer();
+        transfer.Add(DataTransferItem.Create(ConversationDragFormat, conversation.Id.ToString("D")));
+        await DragDrop.DoDragDropAsync(e, transfer, DragDropEffects.Move);
+    }
+
+    private void Conversation_DragOver(object? sender, DragEventArgs e)
+    {
+        e.DragEffects = e.DataTransfer.Contains(ConversationDragFormat) && sender is Button { DataContext: Codev.Conversation }
+            ? DragDropEffects.Move : DragDropEffects.None;
+    }
+
+    private void Conversation_Drop(object? sender, DragEventArgs e)
+    {
+        if (sender is not Button { DataContext: Codev.Conversation target } button ||
+            e.DataTransfer.TryGetValue(ConversationDragFormat) is not { } rawId || !Guid.TryParse(rawId, out var draggedId)) return;
+        e.Handled = true;
+        var insertAfter = e.GetPosition(button).Y >= button.Bounds.Height / 2;
+        if (DataContext is ViewModels.MainViewModel viewModel)
+            viewModel.ReorderConversation(draggedId, target, insertAfter);
+    }
+
     private async void AddTaskChecklistItem_Click(object? sender, RoutedEventArgs e)
     {
         if (DataContext is not ViewModels.MainViewModel viewModel || !viewModel.CanEditTaskChecklist) return;
diff --git a/Codev.Core/ConversationBackupService.cs b/Codev.Core/ConversationBackupService.cs
index 50f59e08..9eec6533 100644
--- a/Codev.Core/ConversationBackupService.cs
+++ b/Codev.Core/ConversationBackupService.cs
@@ -51,6 +51,7 @@ public static string Export(IEnumerable<Conversation> conversations, JsonSeriali
             CompactionThroughMessageCount = conversation.CompactionThroughMessageCount,
             TaskChecklist = TaskChecklistService.NormalizeImported(conversation.TaskChecklist).ToList(),
             IsPinned = conversation.IsPinned,
+            SidebarOrder = conversation.SidebarOrder,
             IsArchived = conversation.IsArchived,
             UpdatedAt = conversation.UpdatedAt,
             ProjectPath = conversation.ProjectPath,
diff --git a/Codev.Core/ConversationPersistence.cs b/Codev.Core/ConversationPersistence.cs
index 5740bebc..b2c03998 100644
--- a/Codev.Core/ConversationPersistence.cs
+++ b/Codev.Core/ConversationPersistence.cs
@@ -51,6 +51,7 @@ public static List<Conversation> CreateSnapshot(IEnumerable<Conversation> conver
             CompactionThroughMessageCount = conversation.CompactionThroughMessageCount,
             TaskChecklist = Codev.TaskChecklistService.NormalizeImported(conversation.TaskChecklist).ToList(),
             IsPinned = conversation.IsPinned,
+            SidebarOrder = conversation.SidebarOrder,
             IsArchived = conversation.IsArchived,
             UpdatedAt = conversation.UpdatedAt,
             ProjectPath = conversation.ProjectPath,
diff --git a/Codev.Core/ConversationSidebarOrdering.cs b/Codev.Core/ConversationSidebarOrdering.cs
new file mode 100644
index 00000000..6ac7fb90
--- /dev/null
+++ b/Codev.Core/ConversationSidebarOrdering.cs
@@ -0,0 +1,30 @@
+namespace Codev;
+
+/// <summary>Moves top-level conversations within a sidebar section and persists their manual order.</summary>
+public static class ConversationSidebarOrdering
+{
+    public static bool TryMove(IList<Conversation> conversations, Guid draggedId, Guid targetId, bool insertAfter)
+    {
+        ArgumentNullException.ThrowIfNull(conversations);
+        if (draggedId == targetId) return false;
+
+        var sourceIndex = IndexOf(draggedId);
+        var targetIndex = IndexOf(targetId);
+        if (sourceIndex < 0 || targetIndex < 0) return false;
+
+        var dragged = conversations[sourceIndex];
+        conversations.RemoveAt(sourceIndex);
+        targetIndex = IndexOf(targetId);
+        conversations.Insert(targetIndex + (insertAfter ? 1 : 0), dragged);
+        for (var index = 0; index < conversations.Count; index++)
+            conversations[index].SidebarOrder = index;
+        return true;
+
+        int IndexOf(Guid id)
+        {
+            for (var index = 0; index < conversations.Count; index++)
+                if (conversations[index].Id == id) return index;
+            return -1;
+        }
+    }
+}
diff --git a/Codev.Core/CoreModels.cs b/Codev.Core/CoreModels.cs
index 4a09ed9b..27009004 100644
--- a/Codev.Core/CoreModels.cs
+++ b/Codev.Core/CoreModels.cs
@@ -69,6 +69,7 @@ [JsonIgnore] public string ChildConversationsLabel
     private List<TaskChecklistItem> _taskChecklist = [];
     public List<TaskChecklistItem> TaskChecklist { get => _taskChecklist; set => _taskChecklist = TaskChecklistService.NormalizeImported(value).ToList(); }
     public bool IsPinned { get; set; }
+    public int? SidebarOrder { get; set; }
     public bool IsArchived { get; set; }
     public DateTimeOffset UpdatedAt { get; set; } = DateTimeOffset.Now;
     public string? ProjectPath { get; set; }
diff --git a/Codev.Tests/ConversationBackupServiceTests.cs b/Codev.Tests/ConversationBackupServiceTests.cs
index 8cf1a4fc..68337e4f 100644
--- a/Codev.Tests/ConversationBackupServiceTests.cs
+++ b/Codev.Tests/ConversationBackupServiceTests.cs
@@ -14,6 +14,7 @@ public void Export_import_round_trip_preserves_history_but_assigns_fresh_runtime
         {
             Id = Guid.NewGuid(),
             Title = "Debug session",
+            SidebarOrder = 4,
             Draft = "an unsent prompt draft",
             Model = "gpt-5.6",
             Provider = CloudModelProviders.OpenAI,
@@ -46,6 +47,7 @@ public void Export_import_round_trip_preserves_history_but_assigns_fresh_runtime
 
         Assert.NotEqual(source.Id, imported.Id);
         Assert.Equal(source.Title, imported.Title);
+        Assert.Equal(source.SidebarOrder, imported.SidebarOrder);
         Assert.Equal(source.Draft, imported.Draft);
         Assert.Equal(source.Model, imported.Model);
         Assert.Equal(CloudModelProviders.OpenAI, imported.Provider);
diff --git a/Codev.Tests/ConversationPersistenceTests.cs b/Codev.Tests/ConversationPersistenceTests.cs
index 2de1a426..35bf1dc3 100644
--- a/Codev.Tests/ConversationPersistenceTests.cs
+++ b/Codev.Tests/ConversationPersistenceTests.cs
@@ -84,6 +84,7 @@ public void Snapshot_detaches_mutable_lists_and_preserves_queued_turn_data()
             IncludeRepoMap = true,
             EnableSemanticSearch = true,
             BestOfNAttempts = 3,
+            SidebarOrder = 7,
             LastPromptTokens = 321,
             LastPromptOutputTokens = 123,
             LastPromptContext = 4096,
@@ -121,6 +122,7 @@ public void Snapshot_detaches_mutable_lists_and_preserves_queued_turn_data()
         Assert.Empty(snapshot.ChildConversations);
         Assert.Equal(CloudModelProviders.OpenAI, snapshot.Provider);
         Assert.False(snapshot.IsPlanMode);
+        Assert.Equal(7, snapshot.SidebarOrder);
         Assert.True(snapshot.IsCodeTask);
         Assert.Equal("Code Reviewer", snapshot.AgentProfileName);
         Assert.False(snapshot.QueueEnabled);
diff --git a/Codev.Tests/ConversationSidebarOrderingTests.cs b/Codev.Tests/ConversationSidebarOrderingTests.cs
new file mode 100644
index 00000000..0b0e76cf
--- /dev/null
+++ b/Codev.Tests/ConversationSidebarOrderingTests.cs
@@ -0,0 +1,34 @@
+namespace Codev.Tests;
+
+public sealed class ConversationSidebarOrderingTests
+{
+    [Theory]
+    [InlineData(false, "a,b,c")]
+    [InlineData(true, "b,a,c")]
+    public void TryMove_reorders_and_assigns_persistable_order(bool insertAfter, string expected)
+    {
+        var conversations = new List<Conversation>
+        {
+            new Conversation { Id = Guid.NewGuid(), Title = "a" },
+            new Conversation { Id = Guid.NewGuid(), Title = "b" },
+            new Conversation { Id = Guid.NewGuid(), Title = "c" }
+        };
+
+        var moved = ConversationSidebarOrdering.TryMove(conversations, conversations[0].Id, conversations[1].Id, insertAfter);
+
+        Assert.True(moved);
+        Assert.Equal(expected.Split(','), conversations.Select(item => item.Title));
+        Assert.Equal(Enumerable.Range(0, 3).Select(index => (int?)index), conversations.Select(item => item.SidebarOrder));
+    }
+
+    [Fact]
+    public void TryMove_rejects_missing_and_identical_items_without_changing_order()
+    {
+        var conversations = new List<Conversation> { new() { Title = "a" }, new() { Title = "b" } };
+        var originalIds = conversations.Select(item => item.Id).ToArray();
+
+        Assert.False(ConversationSidebarOrdering.TryMove(conversations, originalIds[0], originalIds[0], insertAfter: false));
+        Assert.False(ConversationSidebarOrdering.TryMove(conversations, Guid.NewGuid(), originalIds[1], insertAfter: false));
+        Assert.Equal(originalIds, conversations.Select(item => item.Id));
+    }
+}
diff --git a/DESIGN.md b/DESIGN.md
index d1e71e6c..f3264fbe 100644
--- a/DESIGN.md
+++ b/DESIGN.md
@@ -30,7 +30,7 @@ This roadmap describes Codev's intended product scope; parity is an evolving goa
 | Avalonia read-only project context | Trusted folders include bounded source excerpts automatically; untrusted folders remain available for chat and browsing, with only explicitly selected files entering context; up to 24 supported files, with sensitive, excluded, unsupported, and outside-project files rejected |
 | Avalonia folder trust | Trust choices are stored locally and revocable; untrusted folders stay usable for chat/browsing and explicit file selection, while automatic project context requires trust; hosted context keeps its separate opt-in |
 | Avalonia conversation portability | Export one conversation as Markdown or standalone offline HTML; export all chats to JSON and additively import a backup without replacing existing history or restoring checkpoint contents |
-| Avalonia conversation organization | Expand/collapse pinned and recent chat sections independently with saved state; rename and permanently delete chats from their sidebar context menu; archive and restore from that menu; active requests and queued turns block archive/delete |
+| Avalonia conversation organization | Expand/collapse pinned and recent chat sections independently with saved state; drag conversations to reorder within either section, with order persisted across restarts; rename and permanently delete chats from their sidebar context menu; archive and restore from that menu; active requests and queued turns block archive/delete |
 | Avalonia queued follow-ups | Prompts can be queued during generation; each turn snapshots its model/context, queued turns persist and restore paused with explicit resume, and queued turns can be canceled. A restored turn stays paused until explicitly resumed, while a fresh prompt in another conversation can run; later prompts in the same conversation wait behind its saved turn. Queue text distinguishes runnable work from saved turns |
 | Avalonia conversation mode shortcut | `Ctrl/Cmd+Shift+M` cycles Chat, Plan, and eligible Code task modes; Code task creates a trusted conversation workspace when needed and supports loopback Ollama or opted-in OpenAI, while preserving project trust and permission policies |
 | Avalonia `/status` | A local status report shows provider/model (including whether Ollama is remote), context window, temperature, mode, project/context scope, folder trust, queue state, and hosted-request state without sending the command to a model |