diff --git a/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs b/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs
index f147261..3d4a5bc 100644
--- a/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs
+++ b/src/ClaudeDo.Ui/ViewModels/Islands/TaskRowViewModel.cs
@@ -37,6 +37,9 @@ public sealed partial class TaskRowViewModel : ViewModelBase
     public bool IsPlanningParent => Status == TaskStatus.Planning || Status == TaskStatus.Planned;
     public bool IsDraft          => Status == TaskStatus.Draft;
 
+    public bool CanOpenPlanningSession   => Status == TaskStatus.Manual && !IsChild;
+    public bool CanResumeOrDiscardPlanning => Status == TaskStatus.Planning;
+
     public string? PlanningBadge => Status switch
     {
         TaskStatus.Planning => "PLANNING",
@@ -76,9 +79,15 @@ public sealed partial class TaskRowViewModel : ViewModelBase
         OnPropertyChanged(nameof(IsPlanningParent));
         OnPropertyChanged(nameof(PlanningBadge));
         OnPropertyChanged(nameof(IsDraft));
+        OnPropertyChanged(nameof(CanOpenPlanningSession));
+        OnPropertyChanged(nameof(CanResumeOrDiscardPlanning));
     }
 
-    partial void OnParentTaskIdChanged(string? value) => OnPropertyChanged(nameof(IsChild));
+    partial void OnParentTaskIdChanged(string? value)
+    {
+        OnPropertyChanged(nameof(IsChild));
+        OnPropertyChanged(nameof(CanOpenPlanningSession));
+    }
 
     partial void OnBranchChanged(string? value)    => OnPropertyChanged(nameof(HasBranch));
     partial void OnLiveTailChanged(string? value)  => OnPropertyChanged(nameof(HasLiveTail));
diff --git a/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml b/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml
index c823226..1e4bdb1 100644
--- a/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml
+++ b/src/ClaudeDo.Ui/Views/Islands/TaskRowView.axaml
@@ -38,6 +38,19 @@
                       IsVisible="{Binding IsQueued}"
                       Click="OnRemoveFromQueueClick"/>
             <Separator/>
+            <MenuItem Header="Open planning Session"
+                      Command="{Binding $parent[ItemsControl].((vm:TasksIslandViewModel)DataContext).OpenPlanningSessionCommand}"
+                      CommandParameter="{Binding}"
+                      IsVisible="{Binding CanOpenPlanningSession}"/>
+            <MenuItem Header="Resume planning Session"
+                      Command="{Binding $parent[ItemsControl].((vm:TasksIslandViewModel)DataContext).ResumePlanningSessionCommand}"
+                      CommandParameter="{Binding}"
+                      IsVisible="{Binding CanResumeOrDiscardPlanning}"/>
+            <MenuItem Header="Discard planning session"
+                      Command="{Binding $parent[ItemsControl].((vm:TasksIslandViewModel)DataContext).DiscardPlanningSessionCommand}"
+                      CommandParameter="{Binding}"
+                      IsVisible="{Binding CanResumeOrDiscardPlanning}"/>
+            <Separator/>
             <MenuItem Header="Schedule for..." Click="OnScheduleForClick"/>
             <MenuItem Header="Clear schedule"
                       IsVisible="{Binding HasSchedule}"