diff --git a/src/gateway/server-runtime-services.ts b/src/gateway/server-runtime-services.ts
index 39376b6c696..5da78182f0f 100644
--- a/src/gateway/server-runtime-services.ts
+++ b/src/gateway/server-runtime-services.ts
@@ -71,35 +71,22 @@ export function startGatewayRuntimeServices(params: {
   minimalTestGateway: boolean;
   cfgAtStart: OpenClawConfig;
   channelManager: GatewayChannelManager;
-  cron: { start: () => Promise<void> };
-  logCron: { error: (message: string) => void };
   log: GatewayRuntimeServiceLogger;
 }): {
   heartbeatRunner: HeartbeatRunner;
   channelHealthMonitor: ChannelHealthMonitor | null;
   stopModelPricingRefresh: () => void;
 } {
-  const heartbeatRunner = params.minimalTestGateway
-    ? createNoopHeartbeatRunner()
-    : startHeartbeatRunner({ cfg: params.cfgAtStart });
+  // Return a noop heartbeat runner for now.  The real runner is created
+  // in activateGatewayScheduledServices() after sidecars finish and
+  // chat.history becomes available.  See #65322.
   const channelHealthMonitor = startGatewayChannelHealthMonitor({
     cfg: params.cfgAtStart,
     channelManager: params.channelManager,
   });
 
-  if (!params.minimalTestGateway) {
-    startGatewayCronWithLogging({
-      cron: params.cron,
-      logCron: params.logCron,
-    });
-    recoverPendingOutboundDeliveries({
-      cfg: params.cfgAtStart,
-      log: params.log,
-    });
-  }
-
   return {
-    heartbeatRunner,
+    heartbeatRunner: createNoopHeartbeatRunner(),
     channelHealthMonitor,
     stopModelPricingRefresh:
       !params.minimalTestGateway && process.env.VITEST !== "1"
@@ -107,3 +94,45 @@ export function startGatewayRuntimeServices(params: {
         : () => {},
   };
 }
+
+/**
+ * Activate cron scheduler and pending delivery recovery AFTER gateway
+ * sidecars are fully started and chat.history is available.
+ *
+ * Previously these ran inside startGatewayRuntimeServices(), which
+ * fires before sidecars finish — creating a race where cron/heartbeat
+ * jobs could call chat.history while it was still marked unavailable.
+ * See: https://github.com/openclaw/openclaw/issues/65322
+ */
+/**
+ * Activate cron scheduler, heartbeat runner, and pending delivery recovery
+ * AFTER gateway sidecars are fully started and chat.history is available.
+ *
+ * Previously these ran inside startGatewayRuntimeServices(), which fires
+ * before sidecars finish — creating a race where cron/heartbeat jobs
+ * could call chat.history while it was still marked unavailable.
+ * See: https://github.com/openclaw/openclaw/issues/65322
+ *
+ * Returns the real heartbeat runner so the caller can update runtimeState.
+ */
+export function activateGatewayScheduledServices(params: {
+  minimalTestGateway: boolean;
+  cfgAtStart: OpenClawConfig;
+  cron: { start: () => Promise<void> };
+  logCron: { error: (message: string) => void };
+  log: GatewayRuntimeServiceLogger;
+}): { heartbeatRunner: HeartbeatRunner } {
+  if (params.minimalTestGateway) {
+    return { heartbeatRunner: createNoopHeartbeatRunner() };
+  }
+  const heartbeatRunner = startHeartbeatRunner({ cfg: params.cfgAtStart });
+  startGatewayCronWithLogging({
+    cron: params.cron,
+    logCron: params.logCron,
+  });
+  recoverPendingOutboundDeliveries({
+    cfg: params.cfgAtStart,
+    log: params.log,
+  });
+  return { heartbeatRunner };
+}
diff --git a/src/gateway/server.impl.ts b/src/gateway/server.impl.ts
index 528e4577f10..29901b2f5ed 100644
--- a/src/gateway/server.impl.ts
+++ b/src/gateway/server.impl.ts
@@ -56,7 +56,10 @@ import { setFallbackGatewayContextResolver } from "./server-plugins.js";
 import { startManagedGatewayConfigReloader } from "./server-reload-handlers.js";
 import { createGatewayRequestContext } from "./server-request-context.js";
 import { resolveGatewayRuntimeConfig } from "./server-runtime-config.js";
-import { startGatewayRuntimeServices } from "./server-runtime-services.js";
+import {
+  activateGatewayScheduledServices,
+  startGatewayRuntimeServices,
+} from "./server-runtime-services.js";
 import { createGatewayRuntimeState } from "./server-runtime-state.js";
 import { startGatewayEventSubscriptions } from "./server-runtime-subscriptions.js";
 import { resolveSessionKeyForRun } from "./server-session-key.js";
@@ -608,8 +611,6 @@ export async function startGatewayServer(
         minimalTestGateway,
         cfgAtStart,
         channelManager,
-        cron: runtimeState.cronState.cron,
-        logCron,
         log,
       }),
     );
@@ -755,6 +756,19 @@ export async function startGatewayServer(
       unavailableGatewayMethods,
     }));
 
+    // Activate cron scheduler, heartbeat runner, and pending delivery
+    // recovery now that sidecars are ready and chat.history is available.
+    // Previously these ran before sidecars finished, causing a race.
+    // See #65322.
+    const activated = activateGatewayScheduledServices({
+      minimalTestGateway,
+      cfgAtStart,
+      cron: runtimeState.cronState.cron,
+      logCron,
+      log,
+    });
+    runtimeState.heartbeatRunner = activated.heartbeatRunner;
+
     runtimeState.configReloader = startManagedGatewayConfigReloader({
       minimalTestGateway,
       initialConfig: cfgAtStart,