diff --git a/apps/server/src/orchestration-v2/Orchestrator.ts b/apps/server/src/orchestration-v2/Orchestrator.ts
index 1d7f907a5196..016d6f2cf222 100644
--- a/apps/server/src/orchestration-v2/Orchestrator.ts
+++ b/apps/server/src/orchestration-v2/Orchestrator.ts
@@ -2602,10 +2602,12 @@ const makeOrchestrator = Effect.fn("orchestrationV2.Orchestrator.layer")(functio
       const automaticQueuedRuns = projection.runs.filter(
         (run) => run.status === "queued" && automaticMessageIds.has(run.userMessageId),
       );
-      const activeRunExists = projection.runs.some(
-        (run) =>
-          ["preparing", "queued", "starting", "running", "waiting"].includes(run.status) &&
-          !automaticQueuedRuns.includes(run),
+      const runningRunExists = projection.runs.some((run) =>
+        ["preparing", "starting", "running", "waiting"].includes(run.status),
+      );
+      // Includes a queue held after a Stop, which otherwise shows no activity.
+      const queuedMessageExists = projection.runs.some(
+        (run) => run.status === "queued" && !automaticQueuedRuns.includes(run),
       );
       const pendingRequests = projection.runtimeRequests.filter(
         (request) => request.status === "pending",
@@ -2613,11 +2615,19 @@ const makeOrchestrator = Effect.fn("orchestrationV2.Orchestrator.layer")(functio
       const blockingRequestExists = pendingRequests.some(
         (request) => request.kind !== "user_input" || request.responseCapability.type !== "message",
       );
-      if (activeRunExists || blockingRequestExists) {
+      // The reason is shown to the user, so it names what to clear first.
+      const blocker = blockingRequestExists
+        ? "is waiting on an approval or question. Answer it before settling."
+        : runningRunExists
+          ? "is still running. Stop it before settling."
+          : queuedMessageExists
+            ? "has a queued message. Send it or remove it from the queue before settling."
+            : null;
+      if (blocker !== null) {
         return yield* new OrchestratorDispatchError({
           commandId: command.commandId,
           commandType: command.type,
-          cause: `Thread ${command.threadId} has active or blocked work and cannot be settled.`,
+          cause: `Thread ${command.threadId} ${blocker}`,
         });
       }
 
diff --git a/apps/server/src/orchestration-v2/runtimeLayer.test.ts b/apps/server/src/orchestration-v2/runtimeLayer.test.ts
index 79411e6fcc55..3290b36c95b4 100644
--- a/apps/server/src/orchestration-v2/runtimeLayer.test.ts
+++ b/apps/server/src/orchestration-v2/runtimeLayer.test.ts
@@ -3365,6 +3365,7 @@ it.layer(layerTest)("OrchestrationV2LayerLive lifecycle", (it) => {
         .pipe(Effect.flip);
 
       assert.equal(error._tag, "OrchestratorDispatchError");
+      assert.equal(error.cause, `Thread ${threadId} is still running. Stop it before settling.`);
       const projection = yield* orchestrator.getThreadProjection(threadId);
       assert.equal(projection.runs[0]?.status, "starting");
       assert.isNull(projection.thread.settledOverride);
@@ -3563,6 +3564,10 @@ it.layer(layerTest)("OrchestrationV2LayerLive lifecycle", (it) => {
         })
         .pipe(Effect.flip);
       assert.equal(error._tag, "OrchestratorDispatchError");
+      assert.equal(
+        error.cause,
+        `Thread ${threadId} has a queued message. Send it or remove it from the queue before settling.`,
+      );
     }),
   );