diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeTaskOutputTail.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeTaskOutputTail.ts
index 6ab23fddbe16c..ff096cdad2913 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeTaskOutputTail.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeTaskOutputTail.ts
@@ -56,9 +56,12 @@ export const tailClaudeTaskOutput = Effect.fn("ClaudeTaskOutputTail.tail")(funct
   readonly onChunk: (chunk: string) => Effect.Effect<void>;
 }) {
   const fileSystem = yield* FileSystem.FileSystem;
-  const pause = Effect.raceFirst(
-    Effect.sleep(CLAUDE_TASK_OUTPUT_POLL_MS).pipe(Effect.as(false)),
-    Deferred.await(input.stop).pipe(Effect.as(true)),
+  const pause = Deferred.await(input.stop).pipe(
+    Effect.as(true),
+    Effect.timeoutOrElse({
+      duration: CLAUDE_TASK_OUTPUT_POLL_MS,
+      orElse: () => Effect.succeed(false),
+    }),
   );
   let file = Option.none<string>();
   for (let attempt = 0; Option.isNone(file); attempt += 1) {
diff --git a/tsconfig.base.json b/tsconfig.base.json
index 00ff7550156c6..63a69752345a9 100644
--- a/tsconfig.base.json
+++ b/tsconfig.base.json
@@ -24,6 +24,7 @@
         "namespaceImportPackages": ["@effect/platform-node", "effect"],
         "effectFn": ["span", "inferred-span", "suggested-span"],
         "diagnosticSeverity": {
+          "raceFirstWithSleepToTimeout": "error",
           "redundantMapError": "error",
           "optionMatchToFromOption": "error",
           "catchToIgnore": "error",