diff --git a/src/headless.ts b/src/headless.ts
index 672ec9725..e27de3f91 100644
--- a/src/headless.ts
+++ b/src/headless.ts
@@ -753,11 +753,17 @@ async function runHeadlessOnce(
 		resolveCompletion = resolve;
 	});
 
-	// Idle timeout — fallback completion detection
+	// Idle timeout — fallback completion detection.
+	// Multi-turn commands (auto, next, discuss, plan) involve LLM thinking
+	// pauses between tool calls that can exceed 15s. Use the longer
+	// new-milestone timeout for those too — without this, headless killed
+	// auto-mode after 2 tool calls when the LLM paused to reason about the
+	// next step (~35s total run, exit "complete" while task barely started).
 	let idleTimer: ReturnType<typeof setTimeout> | null = null;
-	const effectiveIdleTimeout = isNewMilestone
-		? NEW_MILESTONE_IDLE_TIMEOUT_MS
-		: IDLE_TIMEOUT_MS;
+	const effectiveIdleTimeout =
+		isNewMilestone || isMultiTurnCommand
+			? NEW_MILESTONE_IDLE_TIMEOUT_MS
+			: IDLE_TIMEOUT_MS;
 
 	function resetIdleTimer(): void {
 		if (idleTimer) clearTimeout(idleTimer);