diff --git a/CHANGELOG.md b/CHANGELOG.md
index b221c0977fe..cb49f5e790d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -43,6 +43,7 @@ Docs: https://docs.openclaw.ai
 
 - Diagnostics: keep webhook/message OTEL attributes and Prometheus delivery labels low-cardinality and omit raw chat/message IDs from spans, so progress-draft and message-tool modes do not leak high-cardinality messaging identifiers.
 - Telegram: render shared interactive reply buttons in reply delivery so plugin approval messages show inline keyboards. (#76238) Thanks @keshavbotagent.
+- Agents/cli-runner: drop a saved `claude-cli` resume sessionId at preparation time when its on-disk transcript no longer exists in `~/.claude/projects/`, so a stale binding from a half-installed `update.run` cannot trap follow-up runs (auto-reply / Telegram direct) in a `claude --resume` timeout loop; the run starts fresh and the new sessionId is written back through the existing post-run flow. (#77030; refs #77011) Thanks @openperf.
 - Release validation: install the cross-OS TypeScript harness through Windows-safe Node/npm shims so native Windows package checks reach the OpenClaw smoke suites instead of exiting before artifact capture. Thanks @vincentkoc.
 - Release validation: let Windows packaged-upgrade checks continue after the shipped 2026.5.2 updater hits its native-module swap cleanup fallback, verifying the fallback-installed candidate through package metadata and downstream smoke instead of crashing on the immediate update-status probe. Thanks @vincentkoc.
 - Doctor/plugins: skip channel-derived official plugin installs when another configured plugin is the effective owner for the same channel, so `doctor --repair` does not reinstall `feishu` while `openclaw-lark` handles `channels.feishu`. Fixes #76623. Thanks @fuyizheng3120.
diff --git a/src/agents/cli-runner/prepare.test.ts b/src/agents/cli-runner/prepare.test.ts
index b64289f7cec..ef966e2787c 100644
--- a/src/agents/cli-runner/prepare.test.ts
+++ b/src/agents/cli-runner/prepare.test.ts
@@ -19,6 +19,11 @@ vi.mock("../../plugins/hook-runner-global.js", () => ({
   getGlobalHookRunner: vi.fn(() => null),
 }));
 
+vi.mock("../../plugin-sdk/anthropic-cli.js", () => ({
+  CLAUDE_CLI_BACKEND_ID: "claude-cli",
+  isClaudeCliProvider: (providerId: string) => providerId === "claude-cli",
+}));
+
 vi.mock("../../tts/tts.js", () => ({
   buildTtsSystemPromptHint: vi.fn(() => undefined),
 }));
@@ -668,4 +673,128 @@ describe("shouldSkipLocalCliCredentialEpoch", () => {
       fs.rmSync(dir, { recursive: true, force: true });
     }
   });
+
+  it("drops the claude-cli sessionId when the on-disk transcript is missing (#77011)", async () => {
+    const { dir, sessionFile } = createSessionFile();
+    try {
+      cliBackendsTesting.setDepsForTest({
+        resolvePluginSetupCliBackend: () => undefined,
+        resolveRuntimeCliBackends: () => [
+          {
+            id: "claude-cli",
+            pluginId: "anthropic",
+            bundleMcp: false,
+            config: {
+              command: "claude",
+              args: ["--print"],
+              resumeArgs: ["--resume", "{sessionId}"],
+              output: "jsonl",
+              input: "stdin",
+              sessionMode: "existing",
+            },
+          },
+        ],
+      });
+      const transcriptCheck = vi.fn(async () => false);
+      setCliRunnerPrepareTestDeps({
+        claudeCliSessionTranscriptHasContent: transcriptCheck,
+      });
+
+      const context = await prepareCliRunContext({
+        sessionId: "session-test",
+        sessionKey: "agent:main:telegram:direct:peer",
+        sessionFile,
+        workspaceDir: dir,
+        prompt: "follow-up",
+        provider: "claude-cli",
+        model: "opus",
+        timeoutMs: 1_000,
+        runId: "run-77011-missing",
+        cliSessionBinding: { sessionId: "stale-claude-sid" },
+        cliSessionId: "stale-claude-sid",
+        config: createCliBackendConfig({ systemPromptOverride: null }),
+      });
+
+      expect(transcriptCheck).toHaveBeenCalledWith({ sessionId: "stale-claude-sid" });
+      expect(context.reusableCliSession).toEqual({ invalidatedReason: "missing-transcript" });
+    } finally {
+      fs.rmSync(dir, { recursive: true, force: true });
+    }
+  });
+
+  it("keeps the claude-cli sessionId when the on-disk transcript is present", async () => {
+    const { dir, sessionFile } = createSessionFile();
+    try {
+      cliBackendsTesting.setDepsForTest({
+        resolvePluginSetupCliBackend: () => undefined,
+        resolveRuntimeCliBackends: () => [
+          {
+            id: "claude-cli",
+            pluginId: "anthropic",
+            bundleMcp: false,
+            config: {
+              command: "claude",
+              args: ["--print"],
+              resumeArgs: ["--resume", "{sessionId}"],
+              output: "jsonl",
+              input: "stdin",
+              sessionMode: "existing",
+            },
+          },
+        ],
+      });
+      const transcriptCheck = vi.fn(async () => true);
+      setCliRunnerPrepareTestDeps({
+        claudeCliSessionTranscriptHasContent: transcriptCheck,
+      });
+
+      const context = await prepareCliRunContext({
+        sessionId: "session-test",
+        sessionKey: "agent:main:telegram:direct:peer",
+        sessionFile,
+        workspaceDir: dir,
+        prompt: "follow-up",
+        provider: "claude-cli",
+        model: "opus",
+        timeoutMs: 1_000,
+        runId: "run-77011-present",
+        cliSessionBinding: { sessionId: "live-claude-sid" },
+        cliSessionId: "live-claude-sid",
+        config: createCliBackendConfig({ systemPromptOverride: null }),
+      });
+
+      expect(transcriptCheck).toHaveBeenCalledWith({ sessionId: "live-claude-sid" });
+      expect(context.reusableCliSession).toEqual({ sessionId: "live-claude-sid" });
+    } finally {
+      fs.rmSync(dir, { recursive: true, force: true });
+    }
+  });
+
+  it("does not probe the transcript for non-claude-cli providers", async () => {
+    const { dir, sessionFile } = createSessionFile();
+    try {
+      const transcriptCheck = vi.fn(async () => false);
+      setCliRunnerPrepareTestDeps({
+        claudeCliSessionTranscriptHasContent: transcriptCheck,
+      });
+
+      const context = await prepareCliRunContext({
+        sessionId: "session-test",
+        sessionFile,
+        workspaceDir: dir,
+        prompt: "latest ask",
+        provider: "test-cli",
+        model: "test-model",
+        timeoutMs: 1_000,
+        runId: "run-77011-other-provider",
+        cliSessionBinding: { sessionId: "test-cli-sid" },
+        config: createCliBackendConfig({ systemPromptOverride: null }),
+      });
+
+      expect(transcriptCheck).not.toHaveBeenCalled();
+      expect(context.reusableCliSession).toEqual({ sessionId: "test-cli-sid" });
+    } finally {
+      fs.rmSync(dir, { recursive: true, force: true });
+    }
+  });
 });
diff --git a/src/agents/cli-runner/prepare.ts b/src/agents/cli-runner/prepare.ts
index 592d4b9e2c9..5f09f201f21 100644
--- a/src/agents/cli-runner/prepare.ts
+++ b/src/agents/cli-runner/prepare.ts
@@ -4,6 +4,7 @@ import {
   createMcpLoopbackServerConfig,
   getActiveMcpLoopbackRuntime,
 } from "../../gateway/mcp-http.loopback-runtime.js";
+import { isClaudeCliProvider } from "../../plugin-sdk/anthropic-cli.js";
 import type {
   CliBackendAuthEpochMode,
   CliBackendPreparedExecution,
@@ -29,6 +30,7 @@ import {
 import { CLI_AUTH_EPOCH_VERSION, resolveCliAuthEpoch } from "../cli-auth-epoch.js";
 import { resolveCliBackendConfig } from "../cli-backends.js";
 import { hashCliSessionText, resolveCliSessionReuse } from "../cli-session.js";
+import { claudeCliSessionTranscriptHasContent } from "../command/attempt-execution.helpers.js";
 import { resolveHeartbeatPromptForSystemPrompt } from "../heartbeat-system-prompt.js";
 import {
   resolveBootstrapMaxChars,
@@ -51,7 +53,7 @@ import {
   loadCliSessionHistoryMessages,
   loadCliSessionReseedMessages,
 } from "./session-history.js";
-import type { PreparedCliRunContext, RunCliAgentParams } from "./types.js";
+import type { CliReusableSession, PreparedCliRunContext, RunCliAgentParams } from "./types.js";
 
 const prepareDeps = {
   makeBootstrapWarn: makeBootstrapWarnImpl,
@@ -62,6 +64,9 @@ const prepareDeps = {
   resolveOpenClawReferencePaths: async (
     params: Parameters<typeof import("../docs-path.js").resolveOpenClawReferencePaths>[0],
   ) => (await import("../docs-path.js")).resolveOpenClawReferencePaths(params),
+  // Surfaced as a dep so tests can stub the on-disk Claude CLI transcript probe
+  // without touching ~/.claude/projects.
+  claudeCliSessionTranscriptHasContent,
 };
 
 export function setCliRunnerPrepareTestDeps(overrides: Partial<typeof prepareDeps>): void {
@@ -256,19 +261,36 @@ export async function prepareCliRunContext(
     ...(preparedBackendEnv ? { env: preparedBackendEnv } : {}),
     ...(preparedBackendCleanup ? { cleanup: preparedBackendCleanup } : {}),
   };
-  const reusableCliSession = params.cliSessionBinding
-    ? resolveCliSessionReuse({
-        binding: params.cliSessionBinding,
-        authProfileId: effectiveAuthProfileId,
-        authEpoch,
-        authEpochVersion: CLI_AUTH_EPOCH_VERSION,
-        extraSystemPromptHash,
-        mcpConfigHash: preparedBackendFinal.mcpConfigHash,
-        mcpResumeHash: preparedBackendFinal.mcpResumeHash,
-      })
-    : params.cliSessionId
-      ? { sessionId: params.cliSessionId }
-      : {};
+  // Pre-flight: if a saved Claude CLI sessionId points at a transcript that no
+  // longer exists on disk (e.g. update.run aborted mid-swap, Claude CLI was
+  // reinstalled, or the projects tree was manually pruned), `claude --resume`
+  // hangs or fails outside the cli-runner session_expired path. The persisted
+  // binding then never gets refreshed, causing every subsequent turn to retry
+  // the same dead sessionId. Drop the binding here so this turn starts fresh
+  // and the post-run flow writes the new sessionId back via setCliSessionBinding.
+  const candidateClaudeCliSessionId =
+    params.cliSessionBinding?.sessionId?.trim() || params.cliSessionId?.trim() || undefined;
+  const claudeCliTranscriptMissing =
+    candidateClaudeCliSessionId !== undefined &&
+    isClaudeCliProvider(params.provider) &&
+    !(await prepareDeps.claudeCliSessionTranscriptHasContent({
+      sessionId: candidateClaudeCliSessionId,
+    }));
+  const reusableCliSession: CliReusableSession = claudeCliTranscriptMissing
+    ? { invalidatedReason: "missing-transcript" }
+    : params.cliSessionBinding
+      ? resolveCliSessionReuse({
+          binding: params.cliSessionBinding,
+          authProfileId: effectiveAuthProfileId,
+          authEpoch,
+          authEpochVersion: CLI_AUTH_EPOCH_VERSION,
+          extraSystemPromptHash,
+          mcpConfigHash: preparedBackendFinal.mcpConfigHash,
+          mcpResumeHash: preparedBackendFinal.mcpResumeHash,
+        })
+      : params.cliSessionId
+        ? { sessionId: params.cliSessionId }
+        : {};
   if (reusableCliSession.invalidatedReason) {
     cliBackendLog.info(
       `cli session reset: provider=${params.provider} reason=${reusableCliSession.invalidatedReason}`,
diff --git a/src/agents/cli-runner/types.ts b/src/agents/cli-runner/types.ts
index 73c1ea43592..810a8221ccc 100644
--- a/src/agents/cli-runner/types.ts
+++ b/src/agents/cli-runner/types.ts
@@ -78,7 +78,12 @@ export type CliPreparedBackend = {
 
 export type CliReusableSession = {
   sessionId?: string;
-  invalidatedReason?: "auth-profile" | "auth-epoch" | "system-prompt" | "mcp";
+  invalidatedReason?:
+    | "auth-profile"
+    | "auth-epoch"
+    | "system-prompt"
+    | "mcp"
+    | "missing-transcript";
 };
 
 export type PreparedCliRunContext = {