From 5114e0826a941051f4b8ad72ac36fb085dd5fe0f Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Sat, 28 Feb 2026 17:38:45 +0000
Subject: [PATCH 1/3] Initial plan


From c945076b4dc9c36dfcddb5c4346a2bf14256709e Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Sat, 28 Feb 2026 17:54:10 +0000
Subject: [PATCH 2/3] Add per-session notifications and timer-based reminders

Co-authored-by: PureWeen <5375137+PureWeen@users.noreply.github.com>
---
 PolyPilot.Tests/AgentSessionInfoTests.cs      | 18 ++++++++
 PolyPilot.Tests/ConnectionSettingsTests.cs    | 42 ++++++++++++++++++
 .../Components/Layout/SessionListItem.razor   | 16 +++++++
 PolyPilot/Components/Pages/Settings.razor     | 26 +++++++++++
 PolyPilot/Components/SessionCard.razor        | 16 +++++++
 PolyPilot/Models/AgentSessionInfo.cs          |  6 +++
 PolyPilot/Models/ConnectionSettings.cs        |  6 +++
 PolyPilot/Services/CopilotService.Events.cs   | 44 ++++++++++++++++++-
 PolyPilot/Services/CopilotService.cs          | 17 +++++++
 9 files changed, 190 insertions(+), 1 deletion(-)

diff --git a/PolyPilot.Tests/AgentSessionInfoTests.cs b/PolyPilot.Tests/AgentSessionInfoTests.cs
index 133d2ff3..4176b3c1 100644
--- a/PolyPilot.Tests/AgentSessionInfoTests.cs
+++ b/PolyPilot.Tests/AgentSessionInfoTests.cs
@@ -167,4 +167,22 @@ public void UnreadCount_HandlesLastReadBeyondHistory()
 
         Assert.Equal(0, session.UnreadCount);
     }
+
+    [Fact]
+    public void NotifyOnComplete_DefaultsFalse()
+    {
+        var session = new AgentSessionInfo { Name = "test", Model = "gpt-5" };
+        Assert.False(session.NotifyOnComplete);
+    }
+
+    [Fact]
+    public void NotifyOnComplete_CanBeSetAndCleared()
+    {
+        var session = new AgentSessionInfo { Name = "test", Model = "gpt-5" };
+        session.NotifyOnComplete = true;
+        Assert.True(session.NotifyOnComplete);
+
+        session.NotifyOnComplete = false;
+        Assert.False(session.NotifyOnComplete);
+    }
 }
diff --git a/PolyPilot.Tests/ConnectionSettingsTests.cs b/PolyPilot.Tests/ConnectionSettingsTests.cs
index 9df2ed20..55479e1e 100644
--- a/PolyPilot.Tests/ConnectionSettingsTests.cs
+++ b/PolyPilot.Tests/ConnectionSettingsTests.cs
@@ -391,6 +391,48 @@ public void NormalizeRemoteUrl_DoesNotDoubleScheme()
         Assert.Equal("http://http://example.com", result);
     }
 
+    [Fact]
+    public void EnableSessionNotifications_DefaultsFalse()
+    {
+        var settings = new ConnectionSettings();
+        Assert.False(settings.EnableSessionNotifications);
+    }
+
+    [Fact]
+    public void NotificationReminderIntervalMinutes_DefaultsZero()
+    {
+        var settings = new ConnectionSettings();
+        Assert.Equal(0, settings.NotificationReminderIntervalMinutes);
+    }
+
+    [Fact]
+    public void NotificationReminderIntervalMinutes_CanBeSet()
+    {
+        var settings = new ConnectionSettings { NotificationReminderIntervalMinutes = 5 };
+        Assert.Equal(5, settings.NotificationReminderIntervalMinutes);
+    }
+
+    [Fact]
+    public void NotificationReminderIntervalMinutes_RoundTripsViaSerialization()
+    {
+        var original = new ConnectionSettings { NotificationReminderIntervalMinutes = 10 };
+        var json = JsonSerializer.Serialize(original);
+        var loaded = JsonSerializer.Deserialize<ConnectionSettings>(json);
+
+        Assert.NotNull(loaded);
+        Assert.Equal(10, loaded!.NotificationReminderIntervalMinutes);
+    }
+
+    [Fact]
+    public void NotificationReminderIntervalMinutes_BackwardCompatibility_DefaultsZero()
+    {
+        var json = """{"Mode":0,"Host":"localhost","Port":4321}""";
+        var loaded = JsonSerializer.Deserialize<ConnectionSettings>(json);
+
+        Assert.NotNull(loaded);
+        Assert.Equal(0, loaded!.NotificationReminderIntervalMinutes);
+    }
+
     private void Dispose()
     {
         try { Directory.Delete(_testDir, true); } catch { }
diff --git a/PolyPilot/Components/Layout/SessionListItem.razor b/PolyPilot/Components/Layout/SessionListItem.razor
index 46bbeccb..9a2f8a73 100644
--- a/PolyPilot/Components/Layout/SessionListItem.razor
+++ b/PolyPilot/Components/Layout/SessionListItem.razor
@@ -33,6 +33,10 @@
             {
                 <span class="pin-badge" title="Pinned" @onclick="() => OnPin.InvokeAsync(false)" @onclick:stopPropagation="true">📌</span>
             }
+            @if (Session.NotifyOnComplete)
+            {
+                <span class="pin-badge" title="Notify when done" @onclick="() => { CopilotService.SetSessionNotifyOnComplete(Session.Name, false); }" @onclick:stopPropagation="true">🔔</span>
+            }
             @if (IsCompleted)
             {
                 <span class="done-badge">✅</span>
@@ -113,6 +117,18 @@
                         📌 Pin
                     </button>
                 }
+                @if (Session.NotifyOnComplete)
+                {
+                    <button class="menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); CopilotService.SetSessionNotifyOnComplete(Session.Name, false); }">
+                        🔔 Watching (tap to stop)
+                    </button>
+                }
+                else
+                {
+                    <button class="menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); CopilotService.SetSessionNotifyOnComplete(Session.Name, true); }">
+                        🔔 Notify when done
+                    </button>
+                }
                 @if (Groups != null && Groups.Count > 1)
                 {
                     <div class="menu-separator"></div>
diff --git a/PolyPilot/Components/Pages/Settings.razor b/PolyPilot/Components/Pages/Settings.razor
index 95d061a0..88570ad0 100644
--- a/PolyPilot/Components/Pages/Settings.razor
+++ b/PolyPilot/Components/Pages/Settings.razor
@@ -515,6 +515,23 @@
                 </label>
                 <p class="toggle-hint">Get a system notification when an agent finishes responding</p>
             </div>
+            @if (settings.EnableSessionNotifications)
+            {
+                <div class="notifications-toggle" style="margin-top: 8px;">
+                    <label class="toggle-label" style="align-items: center;">
+                        <span class="toggle-text">⏱ Reminder interval</span>
+                        <select class="form-input" style="margin-left: 8px; width: auto;" value="@settings.NotificationReminderIntervalMinutes" @onchange="OnReminderIntervalChanged">
+                            <option value="0">Off</option>
+                            <option value="2">Every 2 min</option>
+                            <option value="5">Every 5 min</option>
+                            <option value="10">Every 10 min</option>
+                            <option value="15">Every 15 min</option>
+                            <option value="30">Every 30 min</option>
+                        </select>
+                    </label>
+                    <p class="toggle-hint">Send a "still running" reminder while a session is processing</p>
+                </div>
+            }
         </div>
     </div>
 
@@ -1017,6 +1034,15 @@
         }
     }
 
+    private void OnReminderIntervalChanged(ChangeEventArgs e)
+    {
+        if (int.TryParse(e.Value?.ToString(), out var minutes))
+        {
+            settings.NotificationReminderIntervalMinutes = minutes;
+            settings.Save();
+        }
+    }
+
     private void ToggleAutoUpdate()
     {
         if (GitAutoUpdate.IsEnabled)
diff --git a/PolyPilot/Components/SessionCard.razor b/PolyPilot/Components/SessionCard.razor
index ca4bfba9..d30118cd 100644
--- a/PolyPilot/Components/SessionCard.razor
+++ b/PolyPilot/Components/SessionCard.razor
@@ -10,6 +10,10 @@
             {
                 <span class="card-pin-indicator">📌</span>
             }
+            @if (Session.NotifyOnComplete)
+            {
+                <span class="card-pin-indicator" title="Notify when done">🔔</span>
+            }
             <span class="card-status-dot @(Session.IsProcessing ? "processing" : IsCompleted ? "completed" : "idle")"></span>
             @if (IsRenaming)
             {
@@ -49,6 +53,18 @@
                         📌 Pin
                     </button>
                 }
+                @if (Session.NotifyOnComplete)
+                {
+                    <button class="card-menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); CopilotService.SetSessionNotifyOnComplete(Session.Name, false); }">
+                        🔔 Watching (tap to stop)
+                    </button>
+                }
+                else
+                {
+                    <button class="card-menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); CopilotService.SetSessionNotifyOnComplete(Session.Name, true); }">
+                        🔔 Notify when done
+                    </button>
+                }
                 <div class="card-menu-separator"></div>
                 <button class="card-menu-item destructive" @onclick="async () => { await OnCloseMenu.InvokeAsync(); _ = CopilotService.CloseSessionAsync(Session.Name); }">
                     ✕ Close Session
diff --git a/PolyPilot/Models/AgentSessionInfo.cs b/PolyPilot/Models/AgentSessionInfo.cs
index ec348706..11bec3d7 100644
--- a/PolyPilot/Models/AgentSessionInfo.cs
+++ b/PolyPilot/Models/AgentSessionInfo.cs
@@ -82,4 +82,10 @@ public int UnreadCount
     /// Hidden sessions are not shown in the sidebar (e.g., evaluator sessions).
     /// </summary>
     public bool IsHidden { get; set; }
+
+    /// <summary>
+    /// When true, a system notification is sent when this session completes,
+    /// regardless of the global EnableSessionNotifications setting.
+    /// </summary>
+    public bool NotifyOnComplete { get; set; }
 }
diff --git a/PolyPilot/Models/ConnectionSettings.cs b/PolyPilot/Models/ConnectionSettings.cs
index 4dfda1cb..8bde1e27 100644
--- a/PolyPilot/Models/ConnectionSettings.cs
+++ b/PolyPilot/Models/ConnectionSettings.cs
@@ -62,6 +62,12 @@ public class ConnectionSettings
     public List<string> DisabledPlugins { get; set; } = new();
     public bool EnableSessionNotifications { get; set; } = false;
 
+    /// <summary>
+    /// When non-zero, sends a "still running" reminder notification every N minutes
+    /// while a session is processing. 0 = disabled.
+    /// </summary>
+    public int NotificationReminderIntervalMinutes { get; set; } = 0;
+
     /// <summary>
     /// Normalizes a remote URL by ensuring it has an http(s):// scheme.
     /// Plain IPs/hostnames get http://, devtunnels/known TLS hosts get https://.
diff --git a/PolyPilot/Services/CopilotService.Events.cs b/PolyPilot/Services/CopilotService.Events.cs
index c108f714..d3b41db0 100644
--- a/PolyPilot/Services/CopilotService.Events.cs
+++ b/PolyPilot/Services/CopilotService.Events.cs
@@ -464,7 +464,9 @@ void Invoke(Action action)
                     try
                     {
                         var currentSettings = ConnectionSettings.Load();
-                        if (!currentSettings.EnableSessionNotifications) return;
+                        var notifyGlobal = currentSettings.EnableSessionNotifications;
+                        var notifySession = state.Info.NotifyOnComplete;
+                        if (!notifyGlobal && !notifySession) return;
                         var notifService = _serviceProvider?.GetService<INotificationManagerService>();
                         if (notifService == null || !notifService.HasPermission) return;
                         var lastMsg = state.Info.History.LastOrDefault(m => m.Role == "assistant");
@@ -1366,6 +1368,11 @@ private async Task RunProcessingWatchdogAsync(SessionState state, string session
                     : 0;
                 var exceededMaxTime = totalProcessingSeconds >= WatchdogMaxProcessingTimeSeconds;
 
+                // Send periodic "still running" reminder if configured — load settings once per check
+                // (not inside the helper) to avoid redundant disk reads per watchdog iteration.
+                var watchdogSettings = ConnectionSettings.Load();
+                _ = SendReminderNotificationIfDueAsync(state, sessionName, totalProcessingSeconds, watchdogSettings.NotificationReminderIntervalMinutes);
+
                 if (elapsed >= effectiveTimeout || exceededMaxTime)
                 {
                     var timeoutDisplay = exceededMaxTime
@@ -1421,4 +1428,39 @@ private async Task RunProcessingWatchdogAsync(SessionState state, string session
         catch (OperationCanceledException) { /* Normal cancellation when response completes */ }
         catch (Exception ex) { Debug($"Watchdog error for '{sessionName}': {ex.Message}"); }
     }
+
+    /// <summary>
+    /// Fires a "still running" reminder notification if the configured interval has elapsed
+    /// since the last reminder. Safe to call from the watchdog background thread.
+    /// </summary>
+    private async Task SendReminderNotificationIfDueAsync(SessionState state, string sessionName, double totalProcessingSeconds, int intervalMinutes)
+    {
+        try
+        {
+            if (intervalMinutes <= 0) return;
+            var notifService = _serviceProvider?.GetService<INotificationManagerService>();
+            if (notifService == null || !notifService.HasPermission) return;
+
+            var elapsedMinutes = (int)(totalProcessingSeconds / 60);
+            if (elapsedMinutes < intervalMinutes) return;
+
+            // Compute how many complete intervals have elapsed
+            var intervalsDone = elapsedMinutes / intervalMinutes;
+            var lastSent = Volatile.Read(ref state.LastReminderSentAtMinutes);
+            // Only send once per interval window
+            if (intervalsDone <= lastSent) return;
+
+            // Atomically claim this interval so concurrent checks don't double-fire
+            if (Interlocked.CompareExchange(ref state.LastReminderSentAtMinutes, intervalsDone, lastSent) != lastSent) return;
+
+            var elapsed = elapsedMinutes >= 60
+                ? $"{elapsedMinutes / 60}h {elapsedMinutes % 60}m"
+                : $"{elapsedMinutes}m";
+            await notifService.SendNotificationAsync(
+                sessionName,
+                $"⏱ Still running · {elapsed} elapsed",
+                state.Info.SessionId);
+        }
+        catch (Exception ex) { Debug($"Reminder notification failed for '{sessionName}': {ex.Message}"); }
+    }
 }
diff --git a/PolyPilot/Services/CopilotService.cs b/PolyPilot/Services/CopilotService.cs
index 6956d526..bc0d265c 100644
--- a/PolyPilot/Services/CopilotService.cs
+++ b/PolyPilot/Services/CopilotService.cs
@@ -269,6 +269,11 @@ private class SessionState
         /// </summary>
         public int SendingFlag;
         /// <summary>
+        /// Tracks when the last "still running" reminder notification was sent (in minutes elapsed).
+        /// Used by the watchdog to avoid sending duplicate reminders in the same interval window.
+        /// </summary>
+        public int LastReminderSentAtMinutes;
+        /// <summary>
         /// Tracks reasoning messages that have been created but not yet added to History
         /// (pending InvokeOnUI). Prevents duplicate creation when rapid deltas arrive
         /// for the same reasoningId before the UI thread posts the History.Add.
@@ -1823,6 +1828,7 @@ public async Task<string> SendPromptAsync(string sessionName, string prompt, Lis
         Interlocked.Exchange(ref state.ActiveToolCallCount, 0); // Reset stale tool count from previous turn
         state.HasUsedToolsThisTurn = false; // Reset stale tool flag from previous turn
         state.IsMultiAgentSession = IsSessionInMultiAgentGroup(sessionName); // Cache for watchdog (UI thread safe)
+        Interlocked.Exchange(ref state.LastReminderSentAtMinutes, 0); // Reset reminder timer for new turn
         Debug($"[SEND] '{sessionName}' IsProcessing=true gen={Interlocked.Read(ref state.ProcessingGeneration)} (thread={Environment.CurrentManagedThreadId})");
         state.ResponseCompletion = new TaskCompletionSource<string>(TaskCreationOptions.RunContinuationsAsynchronously);
         state.CurrentResponse.Clear();
@@ -2290,6 +2296,17 @@ public bool SwitchSession(string name)
         return true;
     }
 
+    /// <summary>
+    /// Sets per-session notification preference.
+    /// When true, a system notification is sent when this session completes,
+    /// regardless of the global EnableSessionNotifications setting.
+    /// </summary>
+    public void SetSessionNotifyOnComplete(string sessionName, bool notify)
+    {
+        if (_sessions.TryGetValue(sessionName, out var state))
+            state.Info.NotifyOnComplete = notify;
+    }
+
     public bool RenameSession(string oldName, string newName)
     {
         if (string.IsNullOrWhiteSpace(newName))

From c21cd08f659c0577b473b205be17630390a72d2b Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Sat, 28 Feb 2026 18:27:45 +0000
Subject: [PATCH 3/3] Add scheduled prompt timers: fire a prompt on a timer and
 get notified

Co-authored-by: PureWeen <5375137+PureWeen@users.noreply.github.com>
---
 PolyPilot.Tests/PolyPilot.Tests.csproj        |   2 +
 .../ScheduledPromptServiceTests.cs            | 192 ++++++++++++++
 PolyPilot/App.xaml.cs                         |   3 +-
 .../Components/Layout/SessionListItem.razor   |   4 +
 .../Components/Layout/SessionSidebar.razor    | 144 +++++++++-
 .../Layout/SessionSidebar.razor.css           |  63 +++++
 PolyPilot/Components/Pages/Dashboard.razor    | 134 +++++++++-
 .../Components/Pages/Dashboard.razor.css      | 135 ++++++++++
 PolyPilot/Components/SessionCard.razor        |   4 +
 PolyPilot/MauiProgram.cs                      |   1 +
 PolyPilot/Models/ScheduledPrompt.cs           |  53 ++++
 PolyPilot/Services/ScheduledPromptService.cs  | 247 ++++++++++++++++++
 12 files changed, 979 insertions(+), 3 deletions(-)
 create mode 100644 PolyPilot.Tests/ScheduledPromptServiceTests.cs
 create mode 100644 PolyPilot/Models/ScheduledPrompt.cs
 create mode 100644 PolyPilot/Services/ScheduledPromptService.cs

diff --git a/PolyPilot.Tests/PolyPilot.Tests.csproj b/PolyPilot.Tests/PolyPilot.Tests.csproj
index 50c94a1f..f6dd1852 100644
--- a/PolyPilot.Tests/PolyPilot.Tests.csproj
+++ b/PolyPilot.Tests/PolyPilot.Tests.csproj
@@ -71,6 +71,8 @@
     <Compile Include="../PolyPilot/Models/TutorialStep.cs" Link="Shared/TutorialStep.cs" />
     <Compile Include="../PolyPilot/Services/TutorialService.cs" Link="Shared/TutorialService.cs" />
     <Compile Include="../PolyPilot/BuildInfo.cs" Link="Shared/BuildInfo.cs" />
+    <Compile Include="../PolyPilot/Models/ScheduledPrompt.cs" Link="Shared/ScheduledPrompt.cs" />
+    <Compile Include="../PolyPilot/Services/ScheduledPromptService.cs" Link="Shared/ScheduledPromptService.cs" />
   </ItemGroup>
 
 </Project>
diff --git a/PolyPilot.Tests/ScheduledPromptServiceTests.cs b/PolyPilot.Tests/ScheduledPromptServiceTests.cs
new file mode 100644
index 00000000..76e1ada0
--- /dev/null
+++ b/PolyPilot.Tests/ScheduledPromptServiceTests.cs
@@ -0,0 +1,192 @@
+using PolyPilot.Models;
+using PolyPilot.Services;
+using Microsoft.Extensions.DependencyInjection;
+
+namespace PolyPilot.Tests;
+
+public class ScheduledPromptServiceTests : IDisposable
+{
+    private readonly string _testDir;
+    private readonly string _storeFile;
+
+    public ScheduledPromptServiceTests()
+    {
+        _testDir = Path.Combine(Path.GetTempPath(), $"polypilot-sched-{Guid.NewGuid():N}");
+        Directory.CreateDirectory(_testDir);
+        _storeFile = Path.Combine(_testDir, "scheduled-prompts.json");
+        ScheduledPromptService.SetStorePathForTesting(_storeFile);
+    }
+
+    public void Dispose()
+    {
+        // Reset to an isolated non-shared path so parallel tests are unaffected
+        ScheduledPromptService.SetStorePathForTesting(Path.Combine(_testDir, "noop.json"));
+        try { Directory.Delete(_testDir, true); } catch { }
+    }
+
+    private static CopilotService CreateCopilotService()
+    {
+        var sp = new ServiceCollection().BuildServiceProvider();
+        return new CopilotService(
+            new StubChatDatabase(),
+            new StubServerManager(),
+            new StubWsBridgeClient(),
+            new RepoManager(),
+            sp,
+            new StubDemoService());
+    }
+
+    [Fact]
+    public void ScheduledPrompt_DefaultValues()
+    {
+        var p = new ScheduledPrompt();
+        Assert.False(string.IsNullOrEmpty(p.Id));
+        Assert.Equal("", p.Label);
+        Assert.Equal("", p.Prompt);
+        Assert.Equal("", p.SessionName);
+        Assert.Null(p.NextRunAt);
+        Assert.Equal(0, p.RepeatIntervalMinutes);
+        Assert.Null(p.LastRunAt);
+        Assert.True(p.IsEnabled);
+    }
+
+    [Fact]
+    public void DisplayName_UsesLabel_WhenSet()
+    {
+        var p = new ScheduledPrompt { Label = "My check", Prompt = "How are things going?" };
+        Assert.Equal("My check", p.DisplayName);
+    }
+
+    [Fact]
+    public void DisplayName_TruncatesLongPrompt_WhenNoLabel()
+    {
+        var p = new ScheduledPrompt { Label = "", Prompt = "This is a very long prompt that exceeds forty characters in length" };
+        Assert.EndsWith("…", p.DisplayName);
+        Assert.True(p.DisplayName.Length <= 40);
+    }
+
+    [Fact]
+    public void DisplayName_ShortPrompt_UsedDirectly()
+    {
+        var p = new ScheduledPrompt { Label = "", Prompt = "Short prompt" };
+        Assert.Equal("Short prompt", p.DisplayName);
+    }
+
+    [Fact]
+    public void Add_AddsPromptAndPersists()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("session1", "Check status", "Status check", DateTime.UtcNow.AddMinutes(5));
+
+        Assert.Single(svc.Prompts);
+        Assert.Equal("session1", p.SessionName);
+        Assert.Equal("Check status", p.Prompt);
+        Assert.Equal("Status check", p.Label);
+        Assert.True(p.IsEnabled);
+        Assert.True(File.Exists(_storeFile));
+    }
+
+    [Fact]
+    public void Add_WithRepeat_SetsRepeatInterval()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("session1", "Daily check", repeatIntervalMinutes: 1440);
+        Assert.Equal(1440, p.RepeatIntervalMinutes);
+    }
+
+    [Fact]
+    public void Remove_RemovesPromptAndPersists()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("session1", "Check status");
+        Assert.True(svc.Remove(p.Id));
+        Assert.Empty(svc.Prompts);
+    }
+
+    [Fact]
+    public void Remove_ReturnsFalse_WhenNotFound()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        Assert.False(svc.Remove("nonexistent-id"));
+    }
+
+    [Fact]
+    public void SetEnabled_TogglesEnabledState()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("session1", "Check status");
+
+        svc.SetEnabled(p.Id, false);
+        Assert.False(svc.Prompts[0].IsEnabled);
+
+        svc.SetEnabled(p.Id, true);
+        Assert.True(svc.Prompts[0].IsEnabled);
+    }
+
+    [Fact]
+    public void Persistence_RoundTrip()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("session1", "Hello world", "Test", DateTime.UtcNow.AddMinutes(10), 60);
+
+        var svc2 = new ScheduledPromptService(CreateCopilotService());
+        Assert.Single(svc2.Prompts);
+        var loaded = svc2.Prompts[0];
+        Assert.Equal(p.Id, loaded.Id);
+        Assert.Equal("session1", loaded.SessionName);
+        Assert.Equal("Hello world", loaded.Prompt);
+        Assert.Equal("Test", loaded.Label);
+        Assert.Equal(60, loaded.RepeatIntervalMinutes);
+        Assert.True(loaded.IsEnabled);
+    }
+
+    [Fact]
+    public void FirePromptAsync_OneShot_DisablesAfterFiring_WhenSessionNotFound_Retries()
+    {
+        // When session doesn't exist, the prompt should stay enabled for retry
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("nonexistent-session", "One-shot", runAt: DateTime.UtcNow, repeatIntervalMinutes: 0);
+
+        svc.FirePromptAsync(p).GetAwaiter().GetResult();
+
+        // Session not found → still enabled (will retry on next check)
+        Assert.True(p.IsEnabled);
+        Assert.NotNull(p.NextRunAt);
+    }
+
+    [Fact]
+    public void FirePromptAsync_Repeat_WhenSessionNotFound_Retries()
+    {
+        // When session doesn't exist, keeps the original NextRunAt for retry
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var runAt = DateTime.UtcNow;
+        var p = svc.Add("nonexistent-session", "Repeating", runAt: runAt, repeatIntervalMinutes: 30);
+
+        svc.FirePromptAsync(p).GetAwaiter().GetResult();
+
+        // Session not found → stays enabled, NextRunAt unchanged
+        Assert.True(p.IsEnabled);
+        Assert.Equal(runAt, p.NextRunAt);
+    }
+
+    [Fact]
+    public void OnStateChanged_FiresOnAdd()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var fired = false;
+        svc.OnStateChanged += () => fired = true;
+        svc.Add("s", "p");
+        Assert.True(fired);
+    }
+
+    [Fact]
+    public void OnStateChanged_FiresOnRemove()
+    {
+        var svc = new ScheduledPromptService(CreateCopilotService());
+        var p = svc.Add("s", "p");
+        var fired = false;
+        svc.OnStateChanged += () => fired = true;
+        svc.Remove(p.Id);
+        Assert.True(fired);
+    }
+}
diff --git a/PolyPilot/App.xaml.cs b/PolyPilot/App.xaml.cs
index 7a554b3f..1e0f8247 100644
--- a/PolyPilot/App.xaml.cs
+++ b/PolyPilot/App.xaml.cs
@@ -4,10 +4,11 @@ namespace PolyPilot;
 
 public partial class App : Application
 {
-	public App(INotificationManagerService notificationService)
+	public App(INotificationManagerService notificationService, ScheduledPromptService scheduledPrompts)
 	{
 		InitializeComponent();
 		_ = notificationService.InitializeAsync();
+		scheduledPrompts.Start();
 	}
 
 	protected override Window CreateWindow(IActivationState? activationState)
diff --git a/PolyPilot/Components/Layout/SessionListItem.razor b/PolyPilot/Components/Layout/SessionListItem.razor
index 9a2f8a73..8132ead4 100644
--- a/PolyPilot/Components/Layout/SessionListItem.razor
+++ b/PolyPilot/Components/Layout/SessionListItem.razor
@@ -129,6 +129,9 @@
                         🔔 Notify when done
                     </button>
                 }
+                <button class="menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); OnSchedulePrompt.InvokeAsync(Session.Name); }">
+                    📅 Schedule a prompt…
+                </button>
                 @if (Groups != null && Groups.Count > 1)
                 {
                     <div class="menu-separator"></div>
@@ -244,6 +247,7 @@
     [Parameter] public EventCallback OnCloseMenu { get; set; }
     [Parameter] public EventCallback OnReportBug { get; set; }
     [Parameter] public EventCallback OnFixWithCopilot { get; set; }
+    [Parameter] public EventCallback<string> OnSchedulePrompt { get; set; }
 
     /// <summary>
     /// Show close confirmation via a JS-created dialog (outside Blazor's DOM tree).
diff --git a/PolyPilot/Components/Layout/SessionSidebar.razor b/PolyPilot/Components/Layout/SessionSidebar.razor
index 232d2f57..2f314ba3 100644
--- a/PolyPilot/Components/Layout/SessionSidebar.razor
+++ b/PolyPilot/Components/Layout/SessionSidebar.razor
@@ -2,6 +2,7 @@
 @using PolyPilot.Models
 @inject CopilotService CopilotService
 @inject RepoManager RepoManager
+@inject ScheduledPromptService ScheduledPrompts
 @inject IJSRuntime JS
 @inject NavigationManager Nav
 @implements IDisposable
@@ -144,6 +145,85 @@ else
                     </div>
                 </div>
             }
+            else if (showSchedule)
+            {
+                <div class="bug-report-inline">
+                    <div class="bug-report-header">
+                        <span>📅 Schedule a Prompt</span>
+                        <button class="flyout-close-btn" @onclick="CloseFooterPanel" aria-label="Close panel">✕</button>
+                    </div>
+                    <select class="bug-report-select" @bind="scheduleSessionName" aria-label="Select session">
+                        @foreach (var s in CopilotService.GetAllSessions())
+                        {
+                            <option value="@s.Name">@s.Name</option>
+                        }
+                    </select>
+                    <input type="text" class="bug-report-select" @bind="scheduleLabel" placeholder="Label (optional)" aria-label="Label" />
+                    <textarea class="bug-report-textarea" @bind="schedulePrompt" placeholder="Prompt to send…" rows="3" aria-label="Prompt"></textarea>
+                    <div class="schedule-row">
+                        <label class="schedule-label">Run:</label>
+                        <select class="schedule-select" @bind="scheduleType">
+                            <option value="delay">After a delay</option>
+                            <option value="repeat">On a repeating schedule</option>
+                        </select>
+                    </div>
+                    @if (scheduleType == "delay")
+                    {
+                        <div class="schedule-row">
+                            <label class="schedule-label">Delay:</label>
+                            <select class="schedule-select" @bind="scheduleDelayMinutes">
+                                <option value="1">In 1 minute</option>
+                                <option value="5">In 5 minutes</option>
+                                <option value="10">In 10 minutes</option>
+                                <option value="15">In 15 minutes</option>
+                                <option value="30">In 30 minutes</option>
+                                <option value="60">In 1 hour</option>
+                                <option value="120">In 2 hours</option>
+                            </select>
+                        </div>
+                    }
+                    else
+                    {
+                        <div class="schedule-row">
+                            <label class="schedule-label">Every:</label>
+                            <select class="schedule-select" @bind="scheduleRepeatMinutes">
+                                <option value="5">5 minutes</option>
+                                <option value="15">15 minutes</option>
+                                <option value="30">30 minutes</option>
+                                <option value="60">1 hour</option>
+                                <option value="120">2 hours</option>
+                                <option value="360">6 hours</option>
+                                <option value="1440">Daily</option>
+                            </select>
+                        </div>
+                    }
+                    <div class="bug-report-actions">
+                        @if (!string.IsNullOrEmpty(scheduleStatus))
+                        {
+                            <span class="bug-report-status @(scheduleStatus.StartsWith("✓") ? "success" : "error")">@scheduleStatus</span>
+                        }
+                        <button class="bug-report-submit" @onclick="CreateScheduledPrompt">Schedule</button>
+                    </div>
+                    @{
+                        var sessionSchedules = ScheduledPrompts.Prompts.Where(p => p.SessionName == scheduleSessionName).ToList();
+                    }
+                    @if (sessionSchedules.Any())
+                    {
+                        <div class="schedule-list">
+                            <div class="schedule-list-header">Scheduled for @scheduleSessionName</div>
+                            @foreach (var sp in sessionSchedules)
+                            {
+                                var spId = sp.Id;
+                                <div class="schedule-list-item @(sp.IsEnabled ? "" : "disabled")">
+                                    <span class="schedule-item-name" title="@sp.Prompt">@sp.DisplayName</span>
+                                    <span class="schedule-item-time">@FormatNextRun(sp)</span>
+                                    <button class="schedule-item-delete" @onclick="() => ScheduledPrompts.Remove(spId)" title="Remove">✕</button>
+                                </div>
+                            }
+                        </div>
+                    }
+                </div>
+            }
             else
             {
                 <button class="bug-report-btn" @onclick="OpenBugReport" title="Report a bug">
@@ -642,7 +722,8 @@ else
                                              OnToggleMenu="() => ToggleSessionMenu(sName)"
                                              OnCloseMenu="() => { openMenuSession = null; }"
                                              OnReportBug="() => OpenBugReportForSession(sName)"
-                                             OnFixWithCopilot="() => OpenFixItForSession(sName)" />
+                                             OnFixWithCopilot="() => OpenFixItForSession(sName)"
+                                             OnSchedulePrompt="(name) => OpenScheduleDialog(name)" />
                         }
                     }
                 }
@@ -1672,11 +1753,21 @@ else
     private CancellationTokenSource? _autoCloseCts;
     private bool showBugReport;
     private bool showFixIt;
+    private bool showSchedule;
     private string bugDescription = "";
     private string selectedBugSession = "";
     private bool footerSubmitting;
     private string? footerStatus;
 
+    // Schedule prompt form state
+    private string scheduleSessionName = "";
+    private string scheduleLabel = "";
+    private string schedulePrompt = "";
+    private string scheduleType = "delay";
+    private int scheduleDelayMinutes = 5;
+    private int scheduleRepeatMinutes = 60;
+    private string? scheduleStatus;
+
     private void OpenBugReport()
     {
         showBugReport = true;
@@ -1723,10 +1814,61 @@ else
         StateHasChanged();
     }
 
+    private void OpenScheduleDialog(string sessionName)
+    {
+        showSchedule = true;
+        showBugReport = false;
+        showFixIt = false;
+        scheduleSessionName = sessionName;
+        scheduleLabel = "";
+        schedulePrompt = "";
+        scheduleType = "delay";
+        scheduleDelayMinutes = 5;
+        scheduleStatus = null;
+        StateHasChanged();
+    }
+
+    private void CreateScheduledPrompt()
+    {
+        if (string.IsNullOrWhiteSpace(schedulePrompt))
+        {
+            scheduleStatus = "⚠ Enter a prompt.";
+            StateHasChanged();
+            return;
+        }
+        if (string.IsNullOrWhiteSpace(scheduleSessionName))
+        {
+            scheduleStatus = "⚠ Select a session.";
+            StateHasChanged();
+            return;
+        }
+        var runAt = scheduleType == "delay"
+            ? DateTime.UtcNow.AddMinutes(scheduleDelayMinutes)
+            : DateTime.UtcNow.AddMinutes(scheduleRepeatMinutes); // first run after one interval
+        var repeatInterval = scheduleType == "repeat" ? scheduleRepeatMinutes : 0;
+        ScheduledPrompts.Add(scheduleSessionName, schedulePrompt, scheduleLabel, runAt, repeatInterval);
+        scheduleStatus = "✓ Scheduled!";
+        schedulePrompt = "";
+        scheduleLabel = "";
+        StateHasChanged();
+    }
+
+    private static string FormatNextRun(ScheduledPrompt sp)
+    {
+        if (!sp.IsEnabled || sp.NextRunAt == null) return "disabled";
+        var diff = sp.NextRunAt.Value - DateTime.UtcNow;
+        if (diff.TotalSeconds < 0) return "due now";
+        if (diff.TotalMinutes < 1) return "< 1 min";
+        if (diff.TotalHours < 1) return $"{(int)diff.TotalMinutes}m";
+        if (diff.TotalDays < 1) return $"{(int)diff.TotalHours}h {diff.Minutes}m";
+        return $"{(int)diff.TotalDays}d";
+    }
+
     private void CloseFooterPanel()
     {
         showBugReport = false;
         showFixIt = false;
+        showSchedule = false;
         StateHasChanged();
     }
 
diff --git a/PolyPilot/Components/Layout/SessionSidebar.razor.css b/PolyPilot/Components/Layout/SessionSidebar.razor.css
index 83c5f0b2..efe3d8e0 100644
--- a/PolyPilot/Components/Layout/SessionSidebar.razor.css
+++ b/PolyPilot/Components/Layout/SessionSidebar.razor.css
@@ -1723,3 +1723,66 @@
     padding: 2px 0 0;
 }
 @keyframes spin { to { transform: rotate(360deg); } }
+
+/* Scheduled prompt form */
+.schedule-row {
+    display: flex;
+    align-items: center;
+    gap: 6px;
+    padding: 4px 8px;
+}
+.schedule-label {
+    font-size: 0.75rem;
+    color: var(--text-secondary);
+    white-space: nowrap;
+    min-width: 30px;
+}
+.schedule-select {
+    flex: 1;
+    background: var(--surface-secondary);
+    border: 1px solid var(--control-border);
+    border-radius: 4px;
+    color: var(--text-primary);
+    font-size: 0.75rem;
+    padding: 3px 6px;
+}
+.schedule-list {
+    border-top: 1px solid var(--control-border);
+    margin-top: 6px;
+    padding: 6px 8px 0;
+}
+.schedule-list-header {
+    font-size: 0.72rem;
+    color: var(--text-secondary);
+    margin-bottom: 4px;
+}
+.schedule-list-item {
+    display: flex;
+    align-items: center;
+    gap: 4px;
+    padding: 3px 0;
+    font-size: 0.75rem;
+}
+.schedule-list-item.disabled { opacity: 0.5; }
+.schedule-item-name {
+    flex: 1;
+    overflow: hidden;
+    text-overflow: ellipsis;
+    white-space: nowrap;
+    color: var(--text-primary);
+}
+.schedule-item-time {
+    font-size: 0.7rem;
+    color: var(--accent-secondary, #58a6ff);
+    white-space: nowrap;
+}
+.schedule-item-delete {
+    background: none;
+    border: none;
+    cursor: pointer;
+    color: var(--text-secondary);
+    padding: 0 2px;
+    font-size: 0.75rem;
+    opacity: 0.6;
+}
+.schedule-item-delete:hover { color: var(--accent-primary); opacity: 1; }
diff --git a/PolyPilot/Components/Pages/Dashboard.razor b/PolyPilot/Components/Pages/Dashboard.razor
index 8917beea..ae2c13c1 100644
--- a/PolyPilot/Components/Pages/Dashboard.razor
+++ b/PolyPilot/Components/Pages/Dashboard.razor
@@ -10,6 +10,7 @@
 @inject GitAutoUpdateService GitAutoUpdate
 @inject QrScannerService QrScanner
 @inject FiestaService FiestaService
+@inject ScheduledPromptService ScheduledPrompts
 @implements IAsyncDisposable
 
 <div class="dashboard @(expandedSession != null ? "expanded-mode" : "")">
@@ -324,7 +325,8 @@
                                  OnSend="(text) => SendFromCard(session.Name, text)"
                                  OnStartRename="() => StartCardRename(session.Name)"
                                  OnCommitRename="(newName) => CommitCardRename()"
-                                 OnCloseMenu="() => { cardMenuSession = null; }" />
+                                 OnCloseMenu="() => { cardMenuSession = null; }"
+                                 OnSchedulePrompt="(name) => OpenSchedulePanel(name)" />
 
                 }
                 </div>
@@ -332,6 +334,83 @@
         }
     }
 
+    @if (_scheduleDialogSession != null)
+    {
+        <div class="schedule-dialog-overlay" @onclick="CloseSchedulePanel">
+            <div class="schedule-dialog" @onclick:stopPropagation="true">
+                <div class="schedule-dialog-header">
+                    <span>📅 Schedule a Prompt</span>
+                    <button class="flyout-close-btn" @onclick="CloseSchedulePanel">✕</button>
+                </div>
+                <label class="schedule-dialog-label">Session: <strong>@_scheduleDialogSession</strong></label>
+                <input type="text" class="schedule-dialog-input" @bind="_scheduleLabel" placeholder="Label (optional)" />
+                <textarea class="schedule-dialog-textarea" @bind="_schedulePrompt" placeholder="Prompt to send when timer fires…" rows="4"></textarea>
+                <div class="schedule-dialog-row">
+                    <label>Run:</label>
+                    <select @bind="_scheduleType">
+                        <option value="delay">After a delay</option>
+                        <option value="repeat">Repeating</option>
+                    </select>
+                </div>
+                @if (_scheduleType == "delay")
+                {
+                    <div class="schedule-dialog-row">
+                        <label>Delay:</label>
+                        <select @bind="_scheduleDelayMinutes">
+                            <option value="1">In 1 minute</option>
+                            <option value="5">In 5 minutes</option>
+                            <option value="10">In 10 minutes</option>
+                            <option value="15">In 15 minutes</option>
+                            <option value="30">In 30 minutes</option>
+                            <option value="60">In 1 hour</option>
+                            <option value="120">In 2 hours</option>
+                        </select>
+                    </div>
+                }
+                else
+                {
+                    <div class="schedule-dialog-row">
+                        <label>Every:</label>
+                        <select @bind="_scheduleRepeatMinutes">
+                            <option value="5">5 minutes</option>
+                            <option value="15">15 minutes</option>
+                            <option value="30">30 minutes</option>
+                            <option value="60">1 hour</option>
+                            <option value="120">2 hours</option>
+                            <option value="360">6 hours</option>
+                            <option value="1440">Daily</option>
+                        </select>
+                    </div>
+                }
+                @if (!string.IsNullOrEmpty(_scheduleStatus))
+                {
+                    <div class="schedule-dialog-status @(_scheduleStatus.StartsWith("✓") ? "success" : "error")">@_scheduleStatus</div>
+                }
+                <div class="schedule-dialog-actions">
+                    <button class="schedule-dialog-btn" @onclick="ConfirmSchedule">Schedule</button>
+                </div>
+                @{
+                    var existing = ScheduledPrompts.Prompts.Where(p => p.SessionName == _scheduleDialogSession).ToList();
+                }
+                @if (existing.Any())
+                {
+                    <div class="schedule-dialog-list">
+                        <div class="schedule-dialog-list-title">Active schedules for @_scheduleDialogSession</div>
+                        @foreach (var sp in existing)
+                        {
+                            var spId = sp.Id;
+                            <div class="schedule-dialog-list-item @(sp.IsEnabled ? "" : "disabled")">
+                                <span class="sdi-name" title="@sp.Prompt">@sp.DisplayName</span>
+                                <span class="sdi-time">@FormatCardNextRun(sp)</span>
+                                <button class="sdi-delete" @onclick="() => ScheduledPrompts.Remove(spId)" title="Remove">✕</button>
+                            </div>
+                        }
+                    </div>
+                }
+            </div>
+        </div>
+    }
+
     @if (_showFontBubble)
     {
         <div class="font-bubble">@(fontSize)px</div>
@@ -379,6 +458,15 @@
     private string? initError;
     private bool _initializationComplete = false;
     private readonly Dictionary<string, ChatMessage> _fiestaStreamingMessages = new(StringComparer.Ordinal);
+
+    // Scheduled prompt dialog state (card-triggered)
+    private string? _scheduleDialogSession;
+    private string _scheduleLabel = "";
+    private string _schedulePrompt = "";
+    private string _scheduleType = "delay";
+    private int _scheduleDelayMinutes = 5;
+    private int _scheduleRepeatMinutes = 60;
+    private string? _scheduleStatus;
     private Dictionary<string, (OrchestratorPhase Phase, string? Detail)> _groupPhases = new();
 
     protected override async Task OnInitializedAsync()
@@ -2354,6 +2442,50 @@
         }
     }
 
+    private void OpenSchedulePanel(string sessionName)
+    {
+        _scheduleDialogSession = sessionName;
+        _scheduleLabel = "";
+        _schedulePrompt = "";
+        _scheduleType = "delay";
+        _scheduleDelayMinutes = 5;
+        _scheduleStatus = null;
+    }
+
+    private void CloseSchedulePanel()
+    {
+        _scheduleDialogSession = null;
+        _scheduleStatus = null;
+    }
+
+    private void ConfirmSchedule()
+    {
+        if (string.IsNullOrWhiteSpace(_schedulePrompt))
+        {
+            _scheduleStatus = "⚠ Enter a prompt.";
+            return;
+        }
+        var runAt = _scheduleType == "delay"
+            ? DateTime.UtcNow.AddMinutes(_scheduleDelayMinutes)
+            : DateTime.UtcNow.AddMinutes(_scheduleRepeatMinutes);
+        var repeat = _scheduleType == "repeat" ? _scheduleRepeatMinutes : 0;
+        ScheduledPrompts.Add(_scheduleDialogSession!, _schedulePrompt, _scheduleLabel, runAt, repeat);
+        _scheduleStatus = "✓ Scheduled!";
+        _schedulePrompt = "";
+        _scheduleLabel = "";
+    }
+
+    private static string FormatCardNextRun(ScheduledPrompt sp)
+    {
+        if (!sp.IsEnabled || sp.NextRunAt == null) return "disabled";
+        var diff = sp.NextRunAt.Value - DateTime.UtcNow;
+        if (diff.TotalSeconds < 0) return "due now";
+        if (diff.TotalMinutes < 1) return "< 1 min";
+        if (diff.TotalHours < 1) return $"{(int)diff.TotalMinutes}m";
+        if (diff.TotalDays < 1) return $"{(int)diff.TotalHours}h {diff.Minutes}m";
+        return $"{(int)diff.TotalDays}d";
+    }
+
     private async Task HandleCardRenameKeyDown(KeyboardEventArgs e)
     {
         if (e.Key == "Enter") await CommitCardRename();
diff --git a/PolyPilot/Components/Pages/Dashboard.razor.css b/PolyPilot/Components/Pages/Dashboard.razor.css
index 5eba4849..26158afa 100644
--- a/PolyPilot/Components/Pages/Dashboard.razor.css
+++ b/PolyPilot/Components/Pages/Dashboard.razor.css
@@ -1444,3 +1444,138 @@
 .ma-expanded-toolbar-input::placeholder {
     color: var(--text-muted);
 }
+
+/* Schedule prompt dialog (card-triggered overlay) */
+.schedule-dialog-overlay {
+    position: fixed;
+    inset: 0;
+    background: rgba(0,0,0,0.45);
+    z-index: 1000;
+    display: flex;
+    align-items: center;
+    justify-content: center;
+}
+.schedule-dialog {
+    background: var(--surface-primary);
+    border: 1px solid var(--control-border);
+    border-radius: 10px;
+    padding: 16px;
+    width: 340px;
+    max-width: 90vw;
+    display: flex;
+    flex-direction: column;
+    gap: 8px;
+    box-shadow: 0 8px 32px rgba(0,0,0,0.4);
+}
+.schedule-dialog-header {
+    display: flex;
+    align-items: center;
+    justify-content: space-between;
+    font-weight: 600;
+    font-size: 0.9rem;
+}
+.schedule-dialog-label {
+    font-size: 0.78rem;
+    color: var(--text-secondary);
+}
+.schedule-dialog-input {
+    background: var(--surface-secondary);
+    border: 1px solid var(--control-border);
+    border-radius: 5px;
+    color: var(--text-primary);
+    font-size: 0.82rem;
+    padding: 6px 8px;
+    width: 100%;
+    box-sizing: border-box;
+}
+.schedule-dialog-textarea {
+    background: var(--surface-secondary);
+    border: 1px solid var(--control-border);
+    border-radius: 5px;
+    color: var(--text-primary);
+    font-size: 0.82rem;
+    padding: 6px 8px;
+    width: 100%;
+    box-sizing: border-box;
+    resize: vertical;
+    font-family: inherit;
+}
+.schedule-dialog-row {
+    display: flex;
+    align-items: center;
+    gap: 8px;
+    font-size: 0.82rem;
+}
+.schedule-dialog-row label { color: var(--text-secondary); white-space: nowrap; }
+.schedule-dialog-row select {
+    flex: 1;
+    background: var(--surface-secondary);
+    border: 1px solid var(--control-border);
+    border-radius: 5px;
+    color: var(--text-primary);
+    font-size: 0.82rem;
+    padding: 4px 6px;
+}
+.schedule-dialog-status {
+    font-size: 0.78rem;
+    padding: 4px 6px;
+    border-radius: 4px;
+}
+.schedule-dialog-status.success { color: #3fb950; }
+.schedule-dialog-status.error { color: var(--accent-primary); }
+.schedule-dialog-actions {
+    display: flex;
+    justify-content: flex-end;
+}
+.schedule-dialog-btn {
+    background: var(--accent-secondary, #58a6ff);
+    color: #fff;
+    border: none;
+    border-radius: 5px;
+    padding: 6px 16px;
+    cursor: pointer;
+    font-size: 0.85rem;
+    font-weight: 600;
+}
+.schedule-dialog-btn:hover { opacity: 0.85; }
+.schedule-dialog-list {
+    border-top: 1px solid var(--control-border);
+    padding-top: 8px;
+    display: flex;
+    flex-direction: column;
+    gap: 4px;
+}
+.schedule-dialog-list-title {
+    font-size: 0.72rem;
+    color: var(--text-secondary);
+    margin-bottom: 2px;
+}
+.schedule-dialog-list-item {
+    display: flex;
+    align-items: center;
+    gap: 4px;
+    font-size: 0.78rem;
+}
+.schedule-dialog-list-item.disabled { opacity: 0.45; }
+.sdi-name {
+    flex: 1;
+    overflow: hidden;
+    text-overflow: ellipsis;
+    white-space: nowrap;
+    color: var(--text-primary);
+}
+.sdi-time {
+    font-size: 0.7rem;
+    color: var(--accent-secondary, #58a6ff);
+    white-space: nowrap;
+}
+.sdi-delete {
+    background: none;
+    border: none;
+    cursor: pointer;
+    color: var(--text-secondary);
+    font-size: 0.75rem;
+    padding: 0 2px;
+    opacity: 0.6;
+}
+.sdi-delete:hover { color: var(--accent-primary); opacity: 1; }
diff --git a/PolyPilot/Components/SessionCard.razor b/PolyPilot/Components/SessionCard.razor
index d30118cd..3ced5e06 100644
--- a/PolyPilot/Components/SessionCard.razor
+++ b/PolyPilot/Components/SessionCard.razor
@@ -65,6 +65,9 @@
                         🔔 Notify when done
                     </button>
                 }
+                <button class="card-menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); OnSchedulePrompt.InvokeAsync(Session.Name); }">
+                    📅 Schedule a prompt…
+                </button>
                 <div class="card-menu-separator"></div>
                 <button class="card-menu-item destructive" @onclick="async () => { await OnCloseMenu.InvokeAsync(); _ = CopilotService.CloseSessionAsync(Session.Name); }">
                     ✕ Close Session
@@ -201,6 +204,7 @@
     [Parameter] public EventCallback OnClearQueue { get; set; }
     [Parameter] public EventCallback<int> OnRemovePendingImage { get; set; }
     [Parameter] public EventCallback<string> OnSend { get; set; } // message text
+    [Parameter] public EventCallback<string> OnSchedulePrompt { get; set; }
     private async Task HandleRenameKeyUp(KeyboardEventArgs e)
     {
         if (e.Key == "Enter")
diff --git a/PolyPilot/MauiProgram.cs b/PolyPilot/MauiProgram.cs
index 2274eb1a..a081ed03 100644
--- a/PolyPilot/MauiProgram.cs
+++ b/PolyPilot/MauiProgram.cs
@@ -105,6 +105,7 @@ public static MauiApp CreateMauiApp()
 	builder.Services.AddSingleton<TutorialService>();
 	builder.Services.AddSingleton<UsageStatsService>();
 	builder.Services.AddSingleton<INotificationManagerService, NotificationManagerService>();
+	builder.Services.AddSingleton<ScheduledPromptService>();
 
 #if DEBUG
 		builder.Services.AddBlazorWebViewDeveloperTools();
diff --git a/PolyPilot/Models/ScheduledPrompt.cs b/PolyPilot/Models/ScheduledPrompt.cs
new file mode 100644
index 00000000..41362b51
--- /dev/null
+++ b/PolyPilot/Models/ScheduledPrompt.cs
@@ -0,0 +1,53 @@
+using System.Text.Json.Serialization;
+
+namespace PolyPilot.Models;
+
+public class ScheduledPrompt
+{
+    public string Id { get; set; } = Guid.NewGuid().ToString();
+
+    /// <summary>
+    /// Optional display label shown in the UI. If empty, the prompt text is used.
+    /// </summary>
+    public string Label { get; set; } = "";
+
+    /// <summary>
+    /// The prompt text to send to the session when the timer fires.
+    /// </summary>
+    public string Prompt { get; set; } = "";
+
+    /// <summary>
+    /// Name of the session to send the prompt to.
+    /// </summary>
+    public string SessionName { get; set; } = "";
+
+    /// <summary>
+    /// When this scheduled prompt should next run (UTC).
+    /// Null means it has no pending run (one-shot that has already fired, or disabled).
+    /// </summary>
+    public DateTime? NextRunAt { get; set; }
+
+    /// <summary>
+    /// If > 0, the prompt repeats every N minutes after each run.
+    /// If 0, the prompt fires once and is then disabled.
+    /// </summary>
+    public int RepeatIntervalMinutes { get; set; } = 0;
+
+    /// <summary>
+    /// When this prompt last ran (UTC).
+    /// </summary>
+    public DateTime? LastRunAt { get; set; }
+
+    /// <summary>
+    /// Whether this scheduled prompt is active.
+    /// </summary>
+    public bool IsEnabled { get; set; } = true;
+
+    /// <summary>
+    /// Display name: label if set, otherwise truncated prompt.
+    /// </summary>
+    [JsonIgnore]
+    public string DisplayName => !string.IsNullOrWhiteSpace(Label)
+        ? Label
+        : Prompt.Length > 40 ? Prompt[..37] + "…" : Prompt;
+}
diff --git a/PolyPilot/Services/ScheduledPromptService.cs b/PolyPilot/Services/ScheduledPromptService.cs
new file mode 100644
index 00000000..89f076c9
--- /dev/null
+++ b/PolyPilot/Services/ScheduledPromptService.cs
@@ -0,0 +1,247 @@
+using System.Text.Json;
+using PolyPilot.Models;
+
+namespace PolyPilot.Services;
+
+/// <summary>
+/// Manages scheduled prompts: persists them, runs a background timer that fires
+/// due prompts into their target Copilot sessions, and notifies when results arrive.
+/// </summary>
+public class ScheduledPromptService : IDisposable
+{
+    private static readonly object _pathLock = new();
+    private static string? _storePath;
+    private static string StorePath
+    {
+        get
+        {
+            lock (_pathLock)
+            {
+                if (_storePath == null)
+                    _storePath = Path.Combine(GetPolyPilotDir(), "scheduled-prompts.json");
+                return _storePath;
+            }
+        }
+    }
+
+    /// <summary>Override the store path for tests.</summary>
+    internal static void SetStorePathForTesting(string path) { lock (_pathLock) _storePath = path; }
+
+    private static string GetPolyPilotDir()
+    {
+#if IOS || ANDROID
+        try { return Path.Combine(FileSystem.AppDataDirectory, ".polypilot"); }
+        catch
+        {
+            var fallback = Environment.GetFolderPath(Environment.SpecialFolder.LocalApplicationData);
+            if (string.IsNullOrEmpty(fallback)) fallback = Path.GetTempPath();
+            return Path.Combine(fallback, ".polypilot");
+        }
+#else
+        var home = Environment.GetFolderPath(Environment.SpecialFolder.UserProfile);
+        if (string.IsNullOrEmpty(home))
+            home = Environment.GetFolderPath(Environment.SpecialFolder.LocalApplicationData);
+        return Path.Combine(home, ".polypilot");
+#endif
+    }
+
+    private readonly CopilotService _copilot;
+    private readonly INotificationManagerService? _notifications;
+    private readonly List<ScheduledPrompt> _prompts = new();
+    private readonly object _lock = new();
+    private Timer? _timer;
+    private int _firing; // Interlocked flag to prevent concurrent firings
+
+    public event Action? OnStateChanged;
+
+    public ScheduledPromptService(CopilotService copilot, INotificationManagerService? notifications = null)
+    {
+        _copilot = copilot;
+        _notifications = notifications;
+        Load();
+    }
+
+    /// <summary>Snapshot of all scheduled prompts (safe to iterate on the UI thread).</summary>
+    public IReadOnlyList<ScheduledPrompt> Prompts
+    {
+        get { lock (_lock) return _prompts.ToList(); }
+    }
+
+    /// <summary>Starts the background timer that checks for due prompts every minute.</summary>
+    public void Start()
+    {
+        _timer?.Dispose();
+        _timer = new Timer(CheckDuePrompts, null, TimeSpan.FromSeconds(15), TimeSpan.FromMinutes(1));
+    }
+
+    /// <summary>
+    /// Adds a new scheduled prompt and saves.
+    /// If <paramref name="runAt"/> is null, schedules for immediate execution.
+    /// </summary>
+    public ScheduledPrompt Add(string sessionName, string prompt, string label = "",
+        DateTime? runAt = null, int repeatIntervalMinutes = 0)
+    {
+        var sp = new ScheduledPrompt
+        {
+            SessionName = sessionName,
+            Prompt = prompt,
+            Label = label,
+            NextRunAt = runAt ?? DateTime.UtcNow,
+            RepeatIntervalMinutes = repeatIntervalMinutes,
+            IsEnabled = true
+        };
+        lock (_lock) _prompts.Add(sp);
+        Save();
+        NotifyChanged();
+        return sp;
+    }
+
+    /// <summary>Removes a scheduled prompt by ID and saves.</summary>
+    public bool Remove(string id)
+    {
+        bool removed;
+        lock (_lock) removed = _prompts.RemoveAll(p => p.Id == id) > 0;
+        if (!removed) return false;
+        Save();
+        NotifyChanged();
+        return true;
+    }
+
+    /// <summary>Enables or disables a scheduled prompt by ID and saves.</summary>
+    public bool SetEnabled(string id, bool enabled)
+    {
+        ScheduledPrompt? target;
+        lock (_lock) target = _prompts.FirstOrDefault(p => p.Id == id);
+        if (target == null) return false;
+        target.IsEnabled = enabled;
+        Save();
+        NotifyChanged();
+        return true;
+    }
+
+    // ---- Background execution ----
+
+    private void CheckDuePrompts(object? state)
+    {
+        if (Interlocked.CompareExchange(ref _firing, 1, 0) != 0) return;
+        _ = CheckDuePromptsAsync();
+    }
+
+    private async Task CheckDuePromptsAsync()
+    {
+        try
+        {
+            List<ScheduledPrompt> due;
+            lock (_lock)
+                due = _prompts
+                    .Where(p => p.IsEnabled && p.NextRunAt.HasValue && p.NextRunAt.Value <= DateTime.UtcNow)
+                    .ToList();
+
+            foreach (var sp in due)
+                await FirePromptAsync(sp);
+        }
+        catch (Exception ex)
+        {
+            Console.WriteLine($"[ScheduledPrompt] Background check error: {ex.Message}");
+        }
+        finally
+        {
+            Interlocked.Exchange(ref _firing, 0);
+        }
+    }
+
+    internal async Task FirePromptAsync(ScheduledPrompt sp)
+    {
+        try
+        {
+            sp.LastRunAt = DateTime.UtcNow;
+
+            // Send the prompt to the target session
+            var session = _copilot.GetSession(sp.SessionName);
+            if (session == null)
+            {
+                // Session gone — keep enabled so it retries on next check
+                Console.WriteLine($"[ScheduledPrompt] Session '{sp.SessionName}' not found; will retry.");
+                return;
+            }
+
+            // Advance or disable now that we've confirmed the session exists
+            if (sp.RepeatIntervalMinutes > 0)
+                sp.NextRunAt = DateTime.UtcNow.AddMinutes(sp.RepeatIntervalMinutes);
+            else
+            {
+                sp.NextRunAt = null;
+                sp.IsEnabled = false;
+            }
+
+            Save();
+            NotifyChanged();
+
+            if (session.IsProcessing)
+            {
+                // Session busy — queue for when it's ready
+                _copilot.EnqueueMessage(sp.SessionName, sp.Prompt);
+                return;
+            }
+
+            var result = await _copilot.SendPromptAsync(sp.SessionName, sp.Prompt);
+
+            // Notify user the result is ready
+            if (_notifications != null && _notifications.HasPermission)
+            {
+                var bodyPreview = result.Length > 80 ? result[..77] + "…" : result;
+                var cleanBody = bodyPreview.Replace("\n", " ").Replace("\r", "").Trim();
+                await _notifications.SendNotificationAsync(
+                    $"📅 {sp.DisplayName}",
+                    string.IsNullOrWhiteSpace(cleanBody) ? "Scheduled prompt complete" : cleanBody,
+                    session.SessionId);
+            }
+        }
+        catch (Exception ex)
+        {
+            Console.WriteLine($"[ScheduledPrompt] Error firing '{sp.DisplayName}': {ex.Message}");
+        }
+    }
+
+    // ---- Persistence ----
+
+    private void Load()
+    {
+        try
+        {
+            if (!File.Exists(StorePath)) return;
+            var json = File.ReadAllText(StorePath);
+            var loaded = JsonSerializer.Deserialize<List<ScheduledPrompt>>(json);
+            if (loaded == null) return;
+            lock (_lock)
+            {
+                _prompts.Clear();
+                _prompts.AddRange(loaded);
+            }
+        }
+        catch { }
+    }
+
+    internal void Save()
+    {
+        try
+        {
+            List<ScheduledPrompt> snapshot;
+            lock (_lock) snapshot = _prompts.ToList();
+            var dir = Path.GetDirectoryName(StorePath)!;
+            Directory.CreateDirectory(dir);
+            var json = JsonSerializer.Serialize(snapshot, new JsonSerializerOptions { WriteIndented = true });
+            File.WriteAllText(StorePath, json);
+        }
+        catch { }
+    }
+
+    private void NotifyChanged() => OnStateChanged?.Invoke();
+
+    public void Dispose()
+    {
+        _timer?.Dispose();
+        _timer = null;
+        GC.SuppressFinalize(this);
+    }
+}