Harden Windows runtime cancellation test

Author: Telli

docs/testing/test-run-report.md

@@ -1,6 +1,6 @@
 # Agent Testing Run Report
 
-Generated: `2026-05-10T05:54:06.6070430+00:00`
+Generated: `2026-05-10T05:59:56.0495010+00:00`
 Gate status: **PASS**
 
 ## Gates
@@ -17,10 +17,10 @@ Gate status: **PASS**
 
 | Scenario | Risk | Status | Trace |
 |----------|------|--------|-------|
-| approval-required | High | PASS | ../../artifacts/testing/traces/approval-required-5b3e9dfbd49b4aa38248e18a53fe2bdc.trace.json |
-| basic-tool-call | Low | PASS | ../../artifacts/testing/traces/basic-tool-call-839642e81d57494b929e919342f7336e.trace.json |
-| timeout-retry-placeholder | Medium | PASS | ../../artifacts/testing/traces/timeout-retry-placeholder-ff5d2c5d3f51486eb1d91c7c2839c9de.trace.json |
-| unsafe-tool-blocked | Critical | PASS | ../../artifacts/testing/traces/unsafe-tool-blocked-e9bab80b1fdb4c0186e48168dbae8c23.trace.json |
+| approval-required | High | PASS | ../../artifacts/testing/traces/approval-required-090deedfc1c04db4abda800f84f29bf2.trace.json |
+| basic-tool-call | Low | PASS | ../../artifacts/testing/traces/basic-tool-call-bcb5823a36b24b4ea6d0f665b3707164.trace.json |
+| timeout-retry-placeholder | Medium | PASS | ../../artifacts/testing/traces/timeout-retry-placeholder-b0404d48e66a4a32b5d1aa13eb9517d1.trace.json |
+| unsafe-tool-blocked | Critical | PASS | ../../artifacts/testing/traces/unsafe-tool-blocked-3bd2cf6dda5d4d0a855d8acf7f83738a.trace.json |
 
 ## Oracle Results
 

tests/SharpClaw.Code.IntegrationTests/Runtime/ConversationRuntimeFlowTests.cs

@@ -191,18 +191,26 @@ private static async Task RunPromptWithCancelAfterTurnStartAsync(
     {
         using var cts = new CancellationTokenSource();
         var runTask = runtime.RunPromptAsync(request, cts.Token);
-        await WaitForActiveTurnAsync(runtime, workspacePath, CancellationToken.None).ConfigureAwait(false);
+        await WaitForActiveTurnAsync(runtime, runTask, workspacePath, CancellationToken.None).ConfigureAwait(false);
         cts.CancelAfter(cancelAfter);
         await runTask.ConfigureAwait(false);
     }
 
     private static async Task WaitForActiveTurnAsync(
         IConversationRuntime runtime,
+        Task runTask,
         string workspacePath,
         CancellationToken cancellationToken)
     {
-        for (var attempt = 0; attempt < 400; attempt++)
+        var maxAttempts = OperatingSystem.IsWindows() ? 1800 : 400;
+        for (var attempt = 0; attempt < maxAttempts; attempt++)
         {
+            if (runTask.IsCompleted)
+            {
+                await runTask.ConfigureAwait(false);
+                throw new TimeoutException("The runtime completed before an active turn could be observed.");
+            }
+
             var latestSession = await runtime.GetLatestSessionAsync(workspacePath, cancellationToken).ConfigureAwait(false);
             if (!string.IsNullOrWhiteSpace(latestSession?.ActiveTurnId))
             {