diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 1add2822a01e9..840d713474a6e 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -6136,6 +6136,73 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       ),
   );
 
+  // regression: #27238 the explanation an AskUserQuestion refers to must be visible text
+  it.effect.each([
+    { tool: "AskUserQuestion", expected: ["assistant_message"] },
+    { tool: "Bash", expected: ["reasoning"] },
+  ] as const)(
+    "shows a lone Claude 5.1+ thinking block before $tool as $expected",
+    ({ tool, expected }) =>
+      Effect.gen(function* () {
+        const harness = yield* makeWakeHarness;
+        yield* harness.runtime.startTurn(
+          makeClaudeTestTurnInput({
+            threadId: harness.threadId,
+            providerThread: harness.providerThread,
+            now: yield* DateTime.now,
+            attemptId: RunAttemptId.make("thinking-before-tool-attempt"),
+            text: "Check the memory file",
+            attachments: [],
+          }),
+        );
+        const explanation = "The memory file is the cause; deleting it loses your notes.";
+        const snapshot = (uuid: string, content: ReadonlyArray<unknown>) =>
+          claudeSdkFrame({
+            type: "assistant",
+            uuid,
+            session_id: WAKE_NATIVE_SESSION,
+            parent_tool_use_id: null,
+            message: { id: "reply-message", model: "claude-opus-5-5", content },
+          });
+        const frames = [
+          snapshot("thinking-snapshot", [
+            { type: "thinking", thinking: explanation, signature: "sig" },
+          ]),
+          snapshot("tool-snapshot", [{ type: "tool_use", id: "tool-1", name: tool, input: {} }]),
+          makeResultFrame({ uuid: "thinking-before-tool-result", result: "" }),
+        ];
+        for (const frame of frames) yield* Queue.offer(harness.sdkMessages, frame);
+        yield* Queue.take(harness.terminalReceipts);
+        const latest = new Map(
+          harness.events.flatMap((event) =>
+            event.type === "turn_item.updated" &&
+            (event.turnItem.type === "reasoning" || event.turnItem.type === "assistant_message")
+              ? [[event.turnItem.id, event.turnItem] as const]
+              : [],
+          ),
+        );
+        const items = [...latest.values()];
+        assert.deepEqual(
+          items.map((item) => item.type),
+          [...expected],
+        );
+        assert.deepEqual(
+          items.map((item) => item.text),
+          [explanation],
+        );
+      }).pipe(
+        Effect.scoped,
+        Effect.provide(
+          Layer.mergeAll(
+            IdAllocator.layer,
+            McpProviderSessions.layer,
+            NodeServices.layer,
+            NodeCrypto.layer,
+          ),
+        ),
+      ),
+  );
+
   // regression: #15892 non-execution metadata is carried through, not guessed from result text
   it.effect.each(["cancelled", "denied", "permission_denied", undefined])(
     "preserves native tool non-execution metadata %s without inferring a denial from text",
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 7b63b7efc0b65..c86e5759d45a8 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -2067,7 +2067,7 @@ function textFromClaudeContent(content: SDKAssistantMessage["message"]["content"
   return content.flatMap((part) => (part.type === "text" ? [part.text] : [])).join("");
 }
 
-// Claude 5.1+ emits at most one pre-tool text block as thinking; treat only a second consecutive thinking block as text.
+// Claude 5.1+ emits at most one pre-tool text block as thinking; treat a second consecutive thinking block, or a lone one before AskUserQuestion, as text.
 function claudeWritesUpdatesAsThinking(model: string): boolean {
   const match = /claude-[a-z]+-(\d+)(?:-(\d{1,2}))?(?!\d)/u.exec(model);
   if (match === null) return false;
@@ -9126,7 +9126,7 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
                   block.type === "tool_use" &&
                   update !== null &&
                   update.messageId === message.message.id &&
-                  update.followsThinking &&
+                  (update.followsThinking || block.name === "AskUserQuestion") &&
                   claudeWritesUpdatesAsThinking(message.message.model)
                 ) {
                   yield* emitAssistantTextArtifacts({