diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0c7b06af9..d7c079912 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -19,6 +19,7 @@
 - Thinking: default to low for reasoning-capable models when no /think or config default is set.
 - Logging: decouple file log levels from console verbosity; verbose-only details are captured when `logging.level` is debug/trace.
 - Build: fix regex literal in tool-meta path detection (watch build error).
+- Auto-reply: add run-level telemetry + typing TTL guardrails to diagnose stuck replies.
 
 ### Docs
 - Skills: add Sheets/Docs examples to gog skill (#128) — thanks @mbelinky.
diff --git a/src/agents/pi-embedded-runner.ts b/src/agents/pi-embedded-runner.ts
index 1fa5e83e0..164a27343 100644
--- a/src/agents/pi-embedded-runner.ts
+++ b/src/agents/pi-embedded-runner.ts
@@ -25,12 +25,14 @@ import {
 import type { ThinkLevel, VerboseLevel } from "../auto-reply/thinking.js";
 import { formatToolAggregate } from "../auto-reply/tool-meta.js";
 import type { ClawdisConfig } from "../config/config.js";
+import { logVerbose } from "../globals.js";
 import { getMachineDisplayName } from "../infra/machine-name.js";
 import { splitMediaFromOutput } from "../media/parse.js";
 import {
   type enqueueCommand,
   enqueueCommandInLane,
 } from "../process/command-queue.js";
+import { defaultRuntime } from "../runtime.js";
 import { CONFIG_DIR, resolveUserPath } from "../utils.js";
 import { resolveClawdisAgentDir } from "./agent-paths.js";
 import { DEFAULT_MODEL, DEFAULT_PROVIDER } from "./defaults.js";
@@ -376,12 +378,16 @@ export async function runEmbeddedPiAgent(params: {
       const apiKey = await getApiKeyForModel(model, authStorage);
       authStorage.setRuntimeApiKey(model.provider, apiKey);
 
-      const thinkingLevel = mapThinkingLevel(params.thinkLevel);
+        const thinkingLevel = mapThinkingLevel(params.thinkLevel);
 
-      await fs.mkdir(resolvedWorkspace, { recursive: true });
-      await ensureSessionHeader({
-        sessionFile: params.sessionFile,
-        sessionId: params.sessionId,
+        logVerbose(
+          `embedded run start: runId=${params.runId} sessionId=${params.sessionId} provider=${provider} model=${modelId} surface=${params.surface ?? "unknown"}`,
+        );
+
+        await fs.mkdir(resolvedWorkspace, { recursive: true });
+        await ensureSessionHeader({
+          sessionFile: params.sessionFile,
+          sessionId: params.sessionId,
         cwd: resolvedWorkspace,
       });
 
@@ -503,12 +509,21 @@ export async function runEmbeddedPiAgent(params: {
           enforceFinalTag: params.enforceFinalTag,
         });
 
-        const abortTimer = setTimeout(
-          () => {
-            abortRun();
-          },
-          Math.max(1, params.timeoutMs),
-        );
+        let abortWarnTimer: NodeJS.Timeout | undefined;
+        const abortTimer = setTimeout(() => {
+          defaultRuntime.warn?.(
+            `embedded run timeout: runId=${params.runId} sessionId=${params.sessionId} timeoutMs=${params.timeoutMs}`,
+          );
+          abortRun();
+          if (!abortWarnTimer) {
+            abortWarnTimer = setTimeout(() => {
+              if (!session.isStreaming) return;
+              defaultRuntime.warn?.(
+                `embedded run abort still streaming: runId=${params.runId} sessionId=${params.sessionId}`,
+              );
+            }, 10_000);
+          }
+        }, Math.max(1, params.timeoutMs));
 
         let messagesSnapshot: AgentMessage[] = [];
         let sessionIdUsed = session.sessionId;
@@ -526,16 +541,28 @@ export async function runEmbeddedPiAgent(params: {
         }
         let promptError: unknown = null;
         try {
+          const promptStartedAt = Date.now();
+          logVerbose(
+            `embedded run prompt start: runId=${params.runId} sessionId=${params.sessionId}`,
+          );
           try {
             await session.prompt(params.prompt);
           } catch (err) {
             promptError = err;
+          } finally {
+            logVerbose(
+              `embedded run prompt end: runId=${params.runId} sessionId=${params.sessionId} durationMs=${Date.now() - promptStartedAt}`,
+            );
           }
           await waitForCompactionRetry();
           messagesSnapshot = session.messages.slice();
           sessionIdUsed = session.sessionId;
         } finally {
           clearTimeout(abortTimer);
+          if (abortWarnTimer) {
+            clearTimeout(abortWarnTimer);
+            abortWarnTimer = undefined;
+          }
           unsubscribe();
           flushToolDebouncer();
           if (ACTIVE_EMBEDDED_RUNS.get(params.sessionId) === queueHandle) {
@@ -613,6 +640,9 @@ export async function runEmbeddedPiAgent(params: {
               p.text || p.mediaUrl || (p.mediaUrls && p.mediaUrls.length > 0),
           );
 
+        logVerbose(
+          `embedded run done: runId=${params.runId} sessionId=${params.sessionId} durationMs=${Date.now() - started} aborted=${aborted}`,
+        );
         return {
           payloads: payloads.length ? payloads : undefined,
           meta: {
diff --git a/src/agents/pi-embedded-subscribe.ts b/src/agents/pi-embedded-subscribe.ts
index 7554f02f4..539a48b22 100644
--- a/src/agents/pi-embedded-subscribe.ts
+++ b/src/agents/pi-embedded-subscribe.ts
@@ -12,6 +12,7 @@ import {
   extractAssistantText,
   inferToolMetaFromArgs,
 } from "./pi-embedded-utils.js";
+import { logVerbose } from "../globals.js";
 
 const THINKING_TAG_RE = /<\s*\/?\s*think(?:ing)?\s*>/gi;
 const THINKING_OPEN_RE = /<\s*think(?:ing)?\s*>/i;
@@ -200,6 +201,9 @@ export function subscribeEmbeddedPiSession(params: {
         const args = (evt as AgentEvent & { args: unknown }).args;
         const meta = inferToolMetaFromArgs(toolName, args);
         toolMetaById.set(toolCallId, meta);
+        logVerbose(
+          `embedded run tool start: runId=${params.runId} tool=${toolName} toolCallId=${toolCallId}`,
+        );
 
         emitAgentEvent({
           runId: params.runId,
@@ -440,9 +444,26 @@ export function subscribeEmbeddedPiSession(params: {
         }
       }
 
+      if (evt.type === "tool_execution_end") {
+        const toolName = String(
+          (evt as AgentEvent & { toolName: string }).toolName,
+        );
+        const toolCallId = String(
+          (evt as AgentEvent & { toolCallId: string }).toolCallId,
+        );
+        logVerbose(
+          `embedded run tool end: runId=${params.runId} tool=${toolName} toolCallId=${toolCallId}`,
+        );
+      }
+
+      if (evt.type === "agent_start") {
+        logVerbose(`embedded run agent start: runId=${params.runId}`);
+      }
+
       if (evt.type === "auto_compaction_start") {
         compactionInFlight = true;
         ensureCompactionPromise();
+        logVerbose(`embedded run compaction start: runId=${params.runId}`);
       }
 
       if (evt.type === "auto_compaction_end") {
@@ -451,12 +472,14 @@ export function subscribeEmbeddedPiSession(params: {
         if (willRetry) {
           noteCompactionRetry();
           resetForCompactionRetry();
+          logVerbose(`embedded run compaction retry: runId=${params.runId}`);
         } else {
           maybeResolveCompactionWait();
         }
       }
 
       if (evt.type === "agent_end") {
+        logVerbose(`embedded run agent end: runId=${params.runId}`);
         toolDebouncer.flush();
         if (pendingCompactionRetry > 0) {
           resolveCompactionRetry();
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index 619590584..dda1eb09b 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -782,17 +782,41 @@ export async function getReplyFromConfig(
   const typingIntervalSeconds =
     typeof configuredTypingSeconds === "number" ? configuredTypingSeconds : 6;
   const typingIntervalMs = typingIntervalSeconds * 1000;
+  const typingTtlMs = Math.min(
+    Math.max(15_000, typingIntervalMs * 5),
+    60_000,
+  );
   const cleanupTyping = () => {
+    if (typingTtlTimer) {
+      clearTimeout(typingTtlTimer);
+      typingTtlTimer = undefined;
+    }
     if (typingTimer) {
       clearInterval(typingTimer);
       typingTimer = undefined;
     }
   };
+  let typingTtlTimer: NodeJS.Timeout | undefined;
+  const refreshTypingTtl = () => {
+    if (!typingIntervalMs || typingIntervalMs <= 0) return;
+    if (typingTtlMs <= 0) return;
+    if (typingTtlTimer) {
+      clearTimeout(typingTtlTimer);
+    }
+    typingTtlTimer = setTimeout(() => {
+      if (!typingTimer) return;
+      defaultRuntime.warn?.(
+        `typing TTL reached (${typingTtlMs}ms); stopping typing indicator`,
+      );
+      cleanupTyping();
+    }, typingTtlMs);
+  };
   const startTypingLoop = async () => {
     if (!opts?.onReplyStart) return;
     if (typingIntervalMs <= 0) return;
     if (typingTimer) return;
     await onReplyStart();
+    refreshTypingTtl();
     typingTimer = setInterval(() => {
       void triggerTyping();
     }, typingIntervalMs);
@@ -801,6 +825,7 @@ export async function getReplyFromConfig(
     const trimmed = text?.trim();
     if (!trimmed) return;
     if (trimmed === SILENT_REPLY_TOKEN) return;
+    refreshTypingTtl();
     await startTypingLoop();
   };
   let transcribedText: string | undefined;