diff --git a/server/src/services/native-runtime/native-session-executor.test.ts b/server/src/services/native-runtime/native-session-executor.test.ts
index 7ab7238f8c..9b62a06ec8 100644
--- a/server/src/services/native-runtime/native-session-executor.test.ts
+++ b/server/src/services/native-runtime/native-session-executor.test.ts
@@ -4128,6 +4128,11 @@ describe("native governed waits", () => {
       payload: { kind: "dynamicToolCall" },
     };
 
+    // A failed tool is terminal too, even when its error event omits kind.
+    // It must not block the later approval tool from parking this run.
+    await observation.observe({ ...replayedEvent, eventType: "item.started", itemId: "failed-command", payload: { kind: "commandExecution" } }, false);
+    await observation.observe({ ...replayedEvent, eventType: "item.failed", itemId: "failed-command", payload: { error: "Command exited with status 1" } }, false);
+
     // A usage event must not park while the card-creation response is held.
     await observation.observe({ ...replayedEvent, eventType: "item.started", itemId: "approval-tool" }, false);
     const usage = { ...replayedEvent, payload: { kind: "usage" } };
diff --git a/server/src/services/native-runtime/native-session-executor.ts b/server/src/services/native-runtime/native-session-executor.ts
index 593c573d90..2f456d5b38 100644
--- a/server/src/services/native-runtime/native-session-executor.ts
+++ b/server/src/services/native-runtime/native-session-executor.ts
@@ -998,9 +998,12 @@ export function createGovernedWaitEventObservation(
       observation = null;
       const kind = record(event.payload).kind;
       const tool = ["dynamicToolCall", "mcpToolCall", "commandExecution"].includes(String(kind));
-      if (tool && event.itemId) {
-        if (event.eventType === "item.started") pendingTools.add(event.itemId);
-        if (event.eventType === "item.completed") pendingTools.delete(event.itemId);
+      if (event.itemId) {
+        if (tool && event.eventType === "item.started") pendingTools.add(event.itemId);
+        // Terminal error events can omit kind; the tracked ID owns cleanup.
+        if (event.eventType === "item.completed" || event.eventType === "item.failed") {
+          pendingTools.delete(event.itemId);
+        }
       }
       // Usage/model messages can arrive while the tool creating the card is
       // still awaiting its response. Parking then interrupts that in-flight