diff --git a/apps/code/src/main/services/cloud-task/service.ts b/apps/code/src/main/services/cloud-task/service.ts
index 59716b068c..db99fc923f 100644
--- a/apps/code/src/main/services/cloud-task/service.ts
+++ b/apps/code/src/main/services/cloud-task/service.ts
@@ -1,10 +1,12 @@
 import type { CloudTaskPermissionRequestUpdate } from "@shared/types";
+import { ANALYTICS_EVENTS } from "@shared/types/analytics";
 import type { StoredLogEntry } from "@shared/types/session-events";
 import { inject, injectable, preDestroy } from "inversify";
 import { MAIN_TOKENS } from "../../di/tokens";
 import { logger } from "../../utils/logger";
 import { TypedEventEmitter } from "../../utils/typed-event-emitter";
 import type { AuthService } from "../auth/service";
+import { trackAppEvent } from "../posthog-analytics";
 import {
   CloudTaskEvent,
   type CloudTaskEvents,
@@ -979,6 +981,21 @@ export class CloudTaskService extends TypedEventEmitter<CloudTaskEvents> {
     const watcher = this.watchers.get(key);
     if (!watcher) return;
 
+    // Track every terminal give-up so cloud-run stream failures are visible in
+    // PostHog. error_title distinguishes the cause; the budget counts separate an
+    // idle Envoy cut from a genuine outage. Best-effort — never block teardown.
+    trackAppEvent(ANALYTICS_EVENTS.CLOUD_STREAM_DISCONNECTED, {
+      task_id: watcher.taskId,
+      run_id: watcher.runId,
+      team_id: watcher.teamId,
+      error_title: error.title,
+      retryable: error.retryable,
+      reconnect_attempts: watcher.reconnectAttempts,
+      stream_error_attempts: watcher.streamErrorAttempts,
+      cumulative_reconnect_attempts: watcher.cumulativeReconnectAttempts,
+      was_bootstrapping: watcher.isBootstrapping,
+    });
+
     watcher.failed = true;
     watcher.isBootstrapping = false;
     watcher.pendingLogEntries = [];
diff --git a/apps/code/src/shared/types/analytics.ts b/apps/code/src/shared/types/analytics.ts
index 23053a9b8b..a5e701366b 100644
--- a/apps/code/src/shared/types/analytics.ts
+++ b/apps/code/src/shared/types/analytics.ts
@@ -229,6 +229,22 @@ export interface AgentSessionErrorProperties {
   error_type: string;
 }
 
+export interface CloudStreamDisconnectedProperties {
+  task_id: string;
+  run_id: string;
+  team_id: number;
+  // The error surfaced to the user (e.g. "Cloud stream disconnected",
+  // "Cloud run unreachable"), so give-up causes can be told apart.
+  error_title: string;
+  retryable: boolean;
+  // Which reconnect budget was exhausted, to separate idle Envoy cuts from
+  // genuine outages: transport reconnects, backend error frames, cumulative.
+  reconnect_attempts: number;
+  stream_error_attempts: number;
+  cumulative_reconnect_attempts: number;
+  was_bootstrapping: boolean;
+}
+
 // Permission events
 export interface PermissionRespondedProperties {
   task_id: string;
@@ -744,6 +760,7 @@ export const ANALYTICS_EVENTS = {
   // Error events
   TASK_CREATION_FAILED: "Task creation failed",
   AGENT_SESSION_ERROR: "Agent session error",
+  CLOUD_STREAM_DISCONNECTED: "Cloud stream disconnected",
 
   // Inbox events
   INBOX_INTEREST_REGISTERED: "Inbox interest registered",
@@ -864,6 +881,7 @@ export type EventPropertyMap = {
   // Error events
   [ANALYTICS_EVENTS.TASK_CREATION_FAILED]: TaskCreationFailedProperties;
   [ANALYTICS_EVENTS.AGENT_SESSION_ERROR]: AgentSessionErrorProperties;
+  [ANALYTICS_EVENTS.CLOUD_STREAM_DISCONNECTED]: CloudStreamDisconnectedProperties;
 
   // Inbox events
   [ANALYTICS_EVENTS.INBOX_INTEREST_REGISTERED]: never;
diff --git a/packages/agent/src/server/agent-server.ts b/packages/agent/src/server/agent-server.ts
index 8c0f4aa72b..3c3bde54eb 100644
--- a/packages/agent/src/server/agent-server.ts
+++ b/packages/agent/src/server/agent-server.ts
@@ -587,6 +587,44 @@ export class AgentServer {
     this.logger.debug("Agent server stopped");
   }
 
+  /**
+   * Mark the run failed after an unrecoverable crash (uncaught exception /
+   * unhandled rejection). Without this a hard death is silent: the run row
+   * stays non-terminal, the desktop client just sees the stream stop and shows
+   * a generic "Cloud stream disconnected", and the workflow only gives up after
+   * the multi-hour inactivity timeout. Best-effort and self-contained so it can
+   * run from a process-level handler with no session context.
+   */
+  async reportFatalError(error: unknown): Promise<void> {
+    const errorMessage = error instanceof Error ? error.message : String(error);
+    this.logger.error("Fatal agent-server error; marking run failed", error);
+
+    try {
+      await this.posthogAPI.updateTaskRun(
+        this.config.taskId,
+        this.config.runId,
+        {
+          status: "failed",
+          error_message: `Agent server crashed: ${errorMessage}`,
+        },
+      );
+    } catch (updateError) {
+      this.logger.error(
+        "Failed to mark run failed after fatal error",
+        updateError,
+      );
+    }
+
+    try {
+      await this.eventStreamSender?.stop();
+    } catch (stopError) {
+      this.logger.error(
+        "Failed to flush event stream after fatal error",
+        stopError,
+      );
+    }
+  }
+
   private authenticateRequest(
     getHeader: (name: string) => string | undefined,
   ): JwtPayload {
diff --git a/packages/agent/src/server/bin.ts b/packages/agent/src/server/bin.ts
index 36bfe7a0e9..c70368ae9a 100644
--- a/packages/agent/src/server/bin.ts
+++ b/packages/agent/src/server/bin.ts
@@ -187,6 +187,27 @@ program
       process.exit(0);
     });
 
+    // A hard crash would otherwise leave the run non-terminal and the user staring
+    // at a generic "Cloud stream disconnected". Mark the run failed before exiting
+    // so the desktop surfaces a real error instead of a silent stall. The deadline
+    // guarantees we exit even if reportFatalError's network calls hang at crash time
+    // (e.g. API unreachable during a restart), so we never block pod shutdown.
+    const FATAL_ERROR_REPORT_DEADLINE_MS = 5_000;
+    const handleFatalError = async (error: unknown) => {
+      try {
+        await Promise.race([
+          server.reportFatalError(error),
+          new Promise((resolve) =>
+            setTimeout(resolve, FATAL_ERROR_REPORT_DEADLINE_MS).unref(),
+          ),
+        ]);
+      } finally {
+        process.exit(1);
+      }
+    };
+    process.on("uncaughtException", handleFatalError);
+    process.on("unhandledRejection", handleFatalError);
+
     await server.start();
   });