src/ClaudeDo.Ui/Services/IWorkerClient.cs

@@ -7,4 +7,5 @@ public interface IWorkerClient
     Task ResumePlanningSessionAsync(string taskId, CancellationToken ct = default);
     Task DiscardPlanningSessionAsync(string taskId, CancellationToken ct = default);
     Task FinalizePlanningSessionAsync(string taskId, bool queueAgentTasks = true, CancellationToken ct = default);
+    Task<int> GetPendingDraftCountAsync(string taskId, CancellationToken ct = default);
 }

src/ClaudeDo.Ui/Services/WorkerClient.cs

@@ -371,6 +371,8 @@ public partial class WorkerClient : ObservableObject, IAsyncDisposable, IWorkerC
         => await DiscardPlanningSessionAsync(taskId, ct);
     async Task IWorkerClient.FinalizePlanningSessionAsync(string taskId, bool queueAgentTasks, CancellationToken ct)
         => await FinalizePlanningSessionAsync(taskId, queueAgentTasks, ct);
+    async Task<int> IWorkerClient.GetPendingDraftCountAsync(string taskId, CancellationToken ct)
+        => await GetPendingDraftCountAsync(taskId, ct);
 
     // DTOs for deserializing hub responses
     private sealed class ActiveTaskDto

src/ClaudeDo.Ui/ViewModels/Islands/TasksIslandViewModel.cs

@@ -5,6 +5,7 @@ using CommunityToolkit.Mvvm.Input;
 using ClaudeDo.Data;
 using ClaudeDo.Data.Models;
 using ClaudeDo.Ui.Services;
+using ClaudeDo.Ui.ViewModels.Modals;
 using Microsoft.EntityFrameworkCore;
 using TaskStatus = ClaudeDo.Data.Models.TaskStatus;
 
@@ -42,6 +43,8 @@ public sealed partial class TasksIslandViewModel : ViewModelBase
     [ObservableProperty] private bool _showOpenLabel;
     [ObservableProperty] private string _completedHeader = "COMPLETED";
 
+    public Func<UnfinishedPlanningModalViewModel, Task>? ShowUnfinishedPlanningModal { get; set; }
+
     public TasksIslandViewModel(IDbContextFactory<ClaudeDoDbContext> dbFactory, IWorkerClient? worker = null)
     {
         _dbFactory = dbFactory;
@@ -390,7 +393,38 @@ public sealed partial class TasksIslandViewModel : ViewModelBase
     private async Task ResumePlanningSessionAsync(TaskRowViewModel? row)
     {
         if (row is null || !row.IsPlanningParent) return;
-        try { await _worker!.ResumePlanningSessionAsync(row.Id); }
+        if (_worker is null) return;
+        try
+        {
+            var draftCount = await _worker.GetPendingDraftCountAsync(row.Id);
+            var modalVm = new UnfinishedPlanningModalViewModel
+            {
+                TaskTitle  = row.Title,
+                DraftCount = draftCount,
+            };
+
+            if (ShowUnfinishedPlanningModal is null)
+                return;
+            await ShowUnfinishedPlanningModal(modalVm);
+
+            var choice = await modalVm.Result.Task;
+
+            switch (choice)
+            {
+                case UnfinishedPlanningModalResult.Resume:
+                    await _worker.ResumePlanningSessionAsync(row.Id);
+                    break;
+                case UnfinishedPlanningModalResult.FinalizeNow:
+                    await _worker.FinalizePlanningSessionAsync(row.Id);
+                    break;
+                case UnfinishedPlanningModalResult.Discard:
+                    await _worker.DiscardPlanningSessionAsync(row.Id);
+                    break;
+                case UnfinishedPlanningModalResult.Cancel:
+                default:
+                    break;
+            }
+        }
         catch { }
     }
 

src/ClaudeDo.Ui/ViewModels/Modals/UnfinishedPlanningModalViewModel.cs

@@ -0,0 +1,27 @@
+using System.Threading.Tasks;
+using CommunityToolkit.Mvvm.ComponentModel;
+using CommunityToolkit.Mvvm.Input;
+
+namespace ClaudeDo.Ui.ViewModels.Modals;
+
+public enum UnfinishedPlanningModalResult
+{
+    Cancel,
+    Resume,
+    FinalizeNow,
+    Discard,
+}
+
+public sealed partial class UnfinishedPlanningModalViewModel : ViewModelBase
+{
+    [ObservableProperty] private string _taskTitle = "";
+    [ObservableProperty] private int _draftCount;
+
+    public TaskCompletionSource<UnfinishedPlanningModalResult> Result { get; } = new();
+    public Action? CloseAction { get; set; }
+
+    [RelayCommand] private void Resume()      { Result.TrySetResult(UnfinishedPlanningModalResult.Resume);      CloseAction?.Invoke(); }
+    [RelayCommand] private void FinalizeNow() { Result.TrySetResult(UnfinishedPlanningModalResult.FinalizeNow); CloseAction?.Invoke(); }
+    [RelayCommand] private void Discard()     { Result.TrySetResult(UnfinishedPlanningModalResult.Discard);     CloseAction?.Invoke(); }
+    [RelayCommand] private void Cancel()      { Result.TrySetResult(UnfinishedPlanningModalResult.Cancel);      CloseAction?.Invoke(); }
+}

src/ClaudeDo.Ui/Views/Islands/TasksIslandView.axaml.cs

@@ -4,6 +4,8 @@ using Avalonia.Input;
 using Avalonia.Interactivity;
 using Avalonia.VisualTree;
 using ClaudeDo.Ui.ViewModels.Islands;
+using ClaudeDo.Ui.ViewModels.Modals;
+using ClaudeDo.Ui.Views.Modals;
 
 namespace ClaudeDo.Ui.Views.Islands;
 
@@ -19,7 +21,19 @@ public partial class TasksIslandView : UserControl
         DataContextChanged += (_, _) =>
         {
             if (DataContext is TasksIslandViewModel vm)
+            {
                 vm.FocusAddTaskRequested += (_, _) => AddTaskBox.Focus();
+                vm.ShowUnfinishedPlanningModal = async (modalVm) =>
+                {
+                    var owner = TopLevel.GetTopLevel(this) as Window;
+                    if (owner is null) { modalVm.CancelCommand.Execute(null); return; }
+                    var modal = new UnfinishedPlanningModalView { DataContext = modalVm };
+                    // Closing via the OS title-bar (if ever enabled) also resolves the TCS.
+                    modal.Closed += (_, _) => modalVm.CancelCommand.Execute(null);
+                    await modal.ShowDialog(owner);
+                    // ShowDialog completes once the window is closed (CloseAction or OS close).
+                };
+            }
         };
     }
 

src/ClaudeDo.Ui/Views/Modals/UnfinishedPlanningModalView.axaml

@@ -0,0 +1,82 @@
+<Window xmlns="https://github.com/avaloniaui"
+        xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+        xmlns:vm="clr-namespace:ClaudeDo.Ui.ViewModels.Modals"
+        x:Class="ClaudeDo.Ui.Views.Modals.UnfinishedPlanningModalView"
+        x:DataType="vm:UnfinishedPlanningModalViewModel"
+        Title="Unfinished planning session"
+        Width="440" Height="200"
+        CanResize="False"
+        SystemDecorations="None"
+        ExtendClientAreaToDecorationsHint="True"
+        WindowStartupLocation="CenterOwner"
+        Background="{DynamicResource SurfaceBrush}">
+
+  <Window.KeyBindings>
+    <KeyBinding Gesture="Escape" Command="{Binding CancelCommand}"/>
+  </Window.KeyBindings>
+
+  <Window.Styles>
+    <Style Selector="Button.primary">
+      <Setter Property="Background" Value="{DynamicResource AccentBrush}"/>
+      <Setter Property="Foreground" Value="{DynamicResource DeepBrush}"/>
+      <Setter Property="FontWeight" Value="SemiBold"/>
+    </Style>
+  </Window.Styles>
+
+  <Border Background="{DynamicResource SurfaceBrush}"
+          BorderBrush="{DynamicResource LineBrush}"
+          BorderThickness="1">
+    <Grid RowDefinitions="36,*,52">
+
+      <!-- Title bar -->
+      <Border Grid.Row="0"
+              x:Name="TitleBar"
+              Background="{DynamicResource DeepBrush}"
+              BorderBrush="{DynamicResource LineBrush}"
+              BorderThickness="0,0,0,1"
+              PointerPressed="TitleBar_PointerPressed">
+        <Grid ColumnDefinitions="*,Auto" Margin="14,0">
+          <TextBlock Text="UNFINISHED PLANNING SESSION"
+                     FontFamily="{DynamicResource MonoFont}"
+                     FontSize="11"
+                     LetterSpacing="1.4"
+                     Foreground="{DynamicResource TextBrush}"
+                     VerticalAlignment="Center"/>
+          <Button Grid.Column="1"
+                  Classes="icon-btn"
+                  Content="✕"
+                  FontSize="12"
+                  Command="{Binding CancelCommand}"
+                  VerticalAlignment="Center"/>
+        </Grid>
+      </Border>
+
+      <!-- Body -->
+      <StackPanel Grid.Row="1" Margin="20,16" Spacing="8">
+        <TextBlock Text="{Binding TaskTitle}"
+                   FontWeight="SemiBold"
+                   Foreground="{DynamicResource TextBrush}"
+                   TextTrimming="CharacterEllipsis"/>
+        <TextBlock Foreground="{DynamicResource TextDimBrush}">
+          <Run Text="{Binding DraftCount}"/>
+          <Run Text=" draft task(s) waiting to be finalized."/>
+        </TextBlock>
+      </StackPanel>
+
+      <!-- Footer -->
+      <Border Grid.Row="2"
+              Background="{DynamicResource DeepBrush}"
+              BorderBrush="{DynamicResource LineBrush}"
+              BorderThickness="0,1,0,0">
+        <StackPanel Orientation="Horizontal" Spacing="8"
+                    HorizontalAlignment="Right" VerticalAlignment="Center"
+                    Margin="16,0">
+          <Button Content="Discard"  Command="{Binding DiscardCommand}"     MinWidth="80"/>
+          <Button Content="Finalize" Command="{Binding FinalizeNowCommand}" MinWidth="80"/>
+          <Button Content="Resume"   Command="{Binding ResumeCommand}"      Classes="primary" MinWidth="80"/>
+        </StackPanel>
+      </Border>
+
+    </Grid>
+  </Border>
+</Window>

src/ClaudeDo.Ui/Views/Modals/UnfinishedPlanningModalView.axaml.cs

@@ -0,0 +1,23 @@
+using Avalonia.Controls;
+using Avalonia.Input;
+
+namespace ClaudeDo.Ui.Views.Modals;
+
+public partial class UnfinishedPlanningModalView : Window
+{
+    public UnfinishedPlanningModalView()
+    {
+        InitializeComponent();
+        DataContextChanged += (_, _) =>
+        {
+            if (DataContext is ViewModels.Modals.UnfinishedPlanningModalViewModel vm)
+                vm.CloseAction = () => Close();
+        };
+    }
+
+    private void TitleBar_PointerPressed(object? sender, PointerPressedEventArgs e)
+    {
+        if (e.GetCurrentPoint(this).Properties.IsLeftButtonPressed)
+            BeginMoveDrag(e);
+    }
+}

tests/ClaudeDo.Worker.Tests/UiVm/TasksIslandViewModelPlanningTests.cs

@@ -24,6 +24,7 @@ sealed class FakeWorkerClient : IWorkerClient
     public Task ResumePlanningSessionAsync(string taskId, CancellationToken ct = default) { ResumePlanningCalls++; return Task.CompletedTask; }
     public Task DiscardPlanningSessionAsync(string taskId, CancellationToken ct = default) { DiscardPlanningCalls++; return Task.CompletedTask; }
     public Task FinalizePlanningSessionAsync(string taskId, bool queueAgentTasks = true, CancellationToken ct = default) { FinalizePlanningCalls++; return Task.CompletedTask; }
+    public Task<int> GetPendingDraftCountAsync(string taskId, CancellationToken ct = default) => Task.FromResult(0);
 }
 
 // ── Helper to build VM with pre-seeded Items ──────────────────────────────────