[Repo Assist] fix: guard bootstrap prompt against already-configured workspaces

src/OpenClaw.Tray.WinUI/Pages/ChatPage.xaml.cs

@@ -496,12 +496,14 @@ private async Task NavigateWhenChatReadyAsync(
             }
 
             WaitingStatusText.Text = LocalizationHelper.GetString("ChatPage_ChatReady");
+            var app = (App)Application.Current;
             var bootstrapped = await OnboardingChatBootstrapper.BootstrapAsync(
                 connectionManager?.OperatorClient,
-                ((App)Application.Current).Settings,
+                app.Settings,
                 TimeSpan.FromSeconds(90),
-                cancellationToken).ConfigureAwait(true);
-            if (!bootstrapped && !((App)Application.Current).Settings.HasInjectedFirstRunBootstrap)
+                cancellationToken,
+                registry: app.Registry).ConfigureAwait(true);
+            if (!bootstrapped && !app.Settings.HasInjectedFirstRunBootstrap)
             {
                 Logger.Warn("[ChatPage] Gateway hatching bootstrap did not complete; navigating to empty chat");
             }

src/OpenClaw.Tray.WinUI/Services/OnboardingChatBootstrapper.cs

@@ -1,3 +1,4 @@
+using OpenClaw.Connection;
 using OpenClaw.Shared;
 using System;
 using System.Collections.Generic;
@@ -36,12 +37,27 @@ public static async Task<bool> BootstrapAsync(
         IOperatorGatewayClient? client,
         SettingsManager settings,
         TimeSpan? completionTimeout = null,
-        CancellationToken cancellationToken = default)
+        CancellationToken cancellationToken = default,
+        GatewayRegistry? registry = null)
     {
         ArgumentNullException.ThrowIfNull(settings);
 
         if (settings.HasInjectedFirstRunBootstrap)
             return true;
+
+        // Guard: if the user already has a configured gateway, treat this as a non-first-run
+        // installation and silently consume the bootstrap gate without sending the prompt.
+        // This prevents the first-run ritual from firing against an already-configured workspace
+        // in cases where the HasInjectedFirstRunBootstrap flag was not persisted (e.g. fresh
+        // app install over an existing workspace, settings migration, or flag reset).
+        if (registry is not null && SetupExistingGatewayClassifier.HasAnyExistingGatewayConnection(
+                registry, settings, SettingsManager.SettingsDirectoryPath))
+        {
+            MarkBootstrapped(settings);
+            Logger.Info("[OnboardingChatBootstrapper] Existing gateway configuration detected; skipping first-run bootstrap prompt.");
+            return true;
+        }
+
         if (client == null || !client.IsConnectedToGateway)
             return false;
         if (Interlocked.CompareExchange(ref s_inFlight, 1, 0) != 0)

tests/OpenClaw.Tray.Tests/OnboardingChatBootstrapperTests.cs

@@ -1,3 +1,4 @@
+using OpenClaw.Connection;
 using OpenClaw.Shared;
 using OpenClawTray.Services;
 using System.Text.Json;
@@ -82,6 +83,92 @@ public async Task BootstrapAsync_DoesNotConsumeGate_WhenCompletionTimesOut()
         Assert.False(settings.HasInjectedFirstRunBootstrap);
     }
 
+    [Fact]
+    public async Task BootstrapAsync_SkipsPromptAndMarksBootstrapped_WhenRegistryHasExistingGatewayWithSharedToken()
+    {
+        var settings = new SettingsManager(_settingsDir);
+        var client = new FakeOperatorGatewayClient { IsConnectedToGateway = true };
+
+        var registryDir = Path.Combine(_settingsDir, "registry-existing");
+        Directory.CreateDirectory(registryDir);
+        var registry = new GatewayRegistry(registryDir);
+        registry.AddOrUpdate(new GatewayRecord
+        {
+            Id = "gw-existing",
+            Url = "ws://192.168.1.10:18789",
+            SharedGatewayToken = "existing-shared-token"
+        });
+
+        var result = await OnboardingChatBootstrapper.BootstrapAsync(client, settings, TimeSpan.FromSeconds(5), registry: registry);
+
+        Assert.True(result, "Should return true when existing gateway is detected.");
+        Assert.Equal(0, client.SendCount);
+        Assert.True(settings.HasInjectedFirstRunBootstrap, "Gate should be marked so the check doesn't repeat.");
+    }
+
+    [Fact]
+    public async Task BootstrapAsync_SkipsPromptAndMarksBootstrapped_WhenRegistryHasExistingGatewayWithBootstrapToken()
+    {
+        var settings = new SettingsManager(_settingsDir);
+        var client = new FakeOperatorGatewayClient { IsConnectedToGateway = true };
+
+        var registryDir = Path.Combine(_settingsDir, "registry-bootstrap");
+        Directory.CreateDirectory(registryDir);
+        var registry = new GatewayRegistry(registryDir);
+        registry.AddOrUpdate(new GatewayRecord
+        {
+            Id = "gw-bootstrap",
+            Url = "ws://my-gateway:18789",
+            BootstrapToken = "existing-bootstrap-token"
+        });
+
+        var result = await OnboardingChatBootstrapper.BootstrapAsync(client, settings, TimeSpan.FromSeconds(5), registry: registry);
+
+        Assert.True(result);
+        Assert.Equal(0, client.SendCount);
+        Assert.True(settings.HasInjectedFirstRunBootstrap);
+    }
+
+    [Fact]
+    public async Task BootstrapAsync_SendsBootstrapPrompt_WhenRegistryIsEmptyAndGatewayIsNew()
+    {
+        var settings = new SettingsManager(_settingsDir);
+        var client = new FakeOperatorGatewayClient { Result = new ChatSendResult { RunId = "run-new" } };
+
+        var registryDir = Path.Combine(_settingsDir, "registry-empty");
+        Directory.CreateDirectory(registryDir);
+        var registry = new GatewayRegistry(registryDir);
+        // Registry has no records — this is a true first-run scenario.
+
+        var task = OnboardingChatBootstrapper.BootstrapAsync(client, settings, TimeSpan.FromSeconds(5), registry: registry);
+        // slopwatch-ignore: SW004 Test delay is an intentional bounded async wait; replacing it would change the scenario under test.
+        await Task.Delay(50);
+        client.RaiseFinalAssistant("run-new");
+        var result = await task;
+
+        Assert.True(result);
+        Assert.Equal(1, client.SendCount);
+        Assert.Equal(OnboardingChatBootstrapper.Message, client.LastMessage);
+        Assert.True(settings.HasInjectedFirstRunBootstrap);
+    }
+
+    [Fact]
+    public async Task BootstrapAsync_SendsBootstrapPrompt_WhenNoRegistryProvided()
+    {
+        var settings = new SettingsManager(_settingsDir);
+        var client = new FakeOperatorGatewayClient { Result = new ChatSendResult { RunId = "run-noregistry" } };
+
+        var task = OnboardingChatBootstrapper.BootstrapAsync(client, settings, TimeSpan.FromSeconds(5));
+        // slopwatch-ignore: SW004 Test delay is an intentional bounded async wait; replacing it would change the scenario under test.
+        await Task.Delay(50);
+        client.RaiseFinalAssistant("run-noregistry");
+        var result = await task;
+
+        Assert.True(result);
+        Assert.Equal(1, client.SendCount);
+        Assert.True(settings.HasInjectedFirstRunBootstrap);
+    }
+
 #pragma warning disable CS0067
     private sealed class FakeOperatorGatewayClient : IOperatorGatewayClient
     {