diff --git a/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs b/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs
index 9b7e576..6090e92 100644
--- a/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs
+++ b/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs
@@ -26,6 +26,7 @@ public sealed partial class TaskRowViewModel : ViewModelBase
     [ObservableProperty] private string? _parentTaskId;
     [ObservableProperty] private bool _isExpanded = true;
     [ObservableProperty] private bool _hasPlanningChildren;
+    [ObservableProperty] private bool _hasQueuedSubtasks;
 
     public DateTime CreatedAt { get; init; }
     public string CreatedAtFormatted => CreatedAt == default ? "—" : $"Created {CreatedAt:MMM d}";
@@ -58,6 +59,7 @@ public sealed partial class TaskRowViewModel : ViewModelBase
     public bool IsRunning   => Status == TaskStatus.Running;
     public bool IsQueued    => Status == TaskStatus.Queued;
     public bool IsWaiting   => Status == TaskStatus.Waiting;
+    public bool CanRemoveFromQueue => IsQueued || HasQueuedSubtasks;
     public bool HasSchedule => ScheduledFor.HasValue;
     public bool HasLiveTail => IsRunning && !string.IsNullOrEmpty(LiveTail);
 
@@ -87,8 +89,12 @@ public sealed partial class TaskRowViewModel : ViewModelBase
         OnPropertyChanged(nameof(IsDraft));
         OnPropertyChanged(nameof(CanOpenPlanningSession));
         OnPropertyChanged(nameof(CanResumeOrDiscardPlanning));
+        OnPropertyChanged(nameof(CanRemoveFromQueue));
     }
 
+    partial void OnHasQueuedSubtasksChanged(bool value)
+        => OnPropertyChanged(nameof(CanRemoveFromQueue));
+
     partial void OnParentTaskIdChanged(string? value)
     {
         OnPropertyChanged(nameof(IsChild));
diff --git a/src/ClaudeDo.Ui/ViewModels/Islands/TasksIslandViewModel.cs b/src/ClaudeDo.Ui/ViewModels/Islands/TasksIslandViewModel.cs
index 4547958..bd26485 100644
--- a/src/ClaudeDo.Ui/ViewModels/Islands/TasksIslandViewModel.cs
+++ b/src/ClaudeDo.Ui/ViewModels/Islands/TasksIslandViewModel.cs
@@ -100,6 +100,15 @@ public sealed partial class TasksIslandViewModel : ViewModelBase
                 else                                  return;
             }
 
+            // Keep the parent's HasQueuedSubtasks flag in sync when a child's status flips.
+            if (entity is not null && !string.IsNullOrEmpty(entity.ParentTaskId))
+            {
+                var parent = Items.FirstOrDefault(r => r.Id == entity.ParentTaskId);
+                if (parent is not null)
+                    parent.HasQueuedSubtasks = Items.Any(r =>
+                        r.ParentTaskId == parent.Id && (r.IsQueued || r.IsWaiting));
+            }
+
             Regroup();
             UpdateSubtitle();
         }
@@ -207,6 +216,16 @@ public sealed partial class TasksIslandViewModel : ViewModelBase
                 if (parentsWithChildren.Contains(r.Id))
                     r.HasPlanningChildren = true;
 
+            // Mark planning parents whose children are currently queued/waiting,
+            // so the dequeue affordance is visible on the parent row.
+            var parentsWithQueuedKids = Items
+                .Where(r => r.IsChild && !string.IsNullOrEmpty(r.ParentTaskId)
+                            && (r.IsQueued || r.IsWaiting))
+                .Select(r => r.ParentTaskId!)
+                .ToHashSet();
+            foreach (var r in Items)
+                r.HasQueuedSubtasks = parentsWithQueuedKids.Contains(r.Id);
+
             Regroup();
             UpdateSubtitle();
         }
@@ -446,9 +465,15 @@ public sealed partial class TasksIslandViewModel : ViewModelBase
     {
         if (row is null || row.IsRunning) return;
         await using var db = await _dbFactory.CreateDbContextAsync();
-        var entity = await db.Tasks.FirstOrDefaultAsync(t => t.Id == row.Id);
+        var entity = await db.Tasks.Include(t => t.Tags).FirstOrDefaultAsync(t => t.Id == row.Id);
         if (entity is null) return;
         entity.Status = TaskStatus.Queued;
+        // Worker queue picker requires the "agent" tag — attach it on explicit enqueue.
+        if (!entity.Tags.Any(t => t.Name == "agent"))
+        {
+            var agentTag = await db.Tags.FirstOrDefaultAsync(t => t.Name == "agent");
+            if (agentTag is not null) entity.Tags.Add(agentTag);
+        }
         await db.SaveChangesAsync();
         row.Status = TaskStatus.Queued;
         if (_worker is not null)
@@ -467,9 +492,30 @@ public sealed partial class TasksIslandViewModel : ViewModelBase
         await using var db = await _dbFactory.CreateDbContextAsync();
         var entity = await db.Tasks.FirstOrDefaultAsync(t => t.Id == row.Id);
         if (entity is null) return;
-        entity.Status = TaskStatus.Manual;
-        await db.SaveChangesAsync();
-        row.Status = TaskStatus.Manual;
+
+        // For a planning parent the dequeue button targets queued/waiting children,
+        // not the parent itself (whose Status is Planning/Planned).
+        if (entity.Status == TaskStatus.Planning || entity.Status == TaskStatus.Planned)
+        {
+            var children = await db.Tasks
+                .Where(t => t.ParentTaskId == row.Id
+                         && (t.Status == TaskStatus.Queued || t.Status == TaskStatus.Waiting))
+                .ToListAsync();
+            foreach (var c in children) c.Status = TaskStatus.Manual;
+            await db.SaveChangesAsync();
+            foreach (var c in children)
+            {
+                var childRow = Items.FirstOrDefault(r => r.Id == c.Id);
+                if (childRow is not null) childRow.Status = TaskStatus.Manual;
+            }
+            row.HasQueuedSubtasks = false;
+        }
+        else
+        {
+            entity.Status = TaskStatus.Manual;
+            await db.SaveChangesAsync();
+            row.Status = TaskStatus.Manual;
+        }
         Regroup();
         UpdateSubtitle();
         TasksChanged?.Invoke(this, EventArgs.Empty);
diff --git a/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml b/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml
index 14cc299..73d2545 100644
--- a/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml
+++ b/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml
@@ -35,7 +35,7 @@
                       IsVisible="{Binding !IsQueued}"
                       Click="OnSendToQueueClick"/>
             <MenuItem Header="Remove from queue"
-                      IsVisible="{Binding IsQueued}"
+                      IsVisible="{Binding CanRemoveFromQueue}"
                       Click="OnRemoveFromQueueClick"/>
             <Separator/>
             <MenuItem Header="Run interactively"
@@ -119,9 +119,9 @@
               <TextBlock Text="{Binding Status}"/>
             </Border>
 
-            <!-- Dequeue button (only when Queued) -->
+            <!-- Dequeue button (visible when row is Queued, or planning parent has queued subtasks) -->
             <Button Classes="icon-btn dequeue-btn"
-                    IsVisible="{Binding IsQueued}"
+                    IsVisible="{Binding CanRemoveFromQueue}"
                     ToolTip.Tip="Remove from queue"
                     Command="{Binding $parent[ItemsControl].((vm:TasksIslandViewModel)DataContext).RemoveFromQueueCommand}"
                     CommandParameter="{Binding}">