fix(outbound): replay queued session context (#66025)

* fix(outbound): preserve replay session context

* fix(outbound): remove user work log

* changelog: note outbound session-context replay fix (#66025)

---------

Co-authored-by: Devin Robison <drobison@nvidia.com>

CHANGELOG.md

@@ -26,6 +26,7 @@ Docs: https://docs.openclaw.ai
 - Browser/CDP: let local attach-only `manual-cdp` profiles reuse the local loopback CDP control plane under strict default policy and remote-class probe timeouts, so tabs/snapshot stop falsely reporting a live local browser session as not running. (#65611, #66080) Thanks @mbelinky.
 - Cron/scheduler: stop inventing short retries when cron next-run calculation returns no valid future slot, and keep a maintenance wake armed so enabled unscheduled jobs recover without entering a refire loop. (#66019, #66083) Thanks @mbelinky.
 - Cron/scheduler: preserve the active error-backoff floor when maintenance repair recomputes a missing cron next-run, so recurring errored jobs do not resume early after a transient next-run resolution failure. (#66019, #66083, #66113) Thanks @mbelinky.
+- Outbound/delivery-queue: persist the originating outbound `session` context on queued delivery entries and replay it during recovery, so write-ahead-queued sends keep their original outbound media policy context after restart instead of evaluating against a missing session. (#66025) Thanks @eleqtrizit.
 
 ## 2026.4.12
 

src/infra/outbound/deliver.ts

@@ -507,6 +507,7 @@ export async function deliverOutboundPayloads(
         forceDocument: params.forceDocument,
         silent: params.silent,
         mirror: params.mirror,
+        session: params.session,
         gatewayClientScopes: params.gatewayClientScopes,
       }).catch(() => null); // Best-effort — don't block delivery if queue write fails.
 

src/infra/outbound/delivery-queue-recovery.ts

@@ -104,6 +104,7 @@ function buildRecoveryDeliverParams(entry: QueuedDelivery, cfg: OpenClawConfig)
     forceDocument: entry.forceDocument,
     silent: entry.silent,
     mirror: entry.mirror,
+    session: entry.session,
     gatewayClientScopes: entry.gatewayClientScopes,
     skipQueue: true, // Prevent re-enqueueing during recovery.
   } satisfies Parameters<DeliverFn>[0];

src/infra/outbound/delivery-queue-storage.ts

@@ -4,6 +4,7 @@ import type { ReplyPayload } from "../../auto-reply/types.js";
 import { resolveStateDir } from "../../config/paths.js";
 import { generateSecureUuid } from "../secure-random.js";
 import type { OutboundMirror } from "./mirror.js";
+import type { OutboundSessionContext } from "./session-context.js";
 import type { OutboundChannel } from "./targets.js";
 
 const QUEUE_DIRNAME = "delivery-queue";
@@ -26,6 +27,8 @@ export type QueuedDeliveryPayload = {
   forceDocument?: boolean;
   silent?: boolean;
   mirror?: OutboundMirror;
+  /** Session context needed to preserve outbound media policy on recovery. */
+  session?: OutboundSessionContext;
   /** Gateway caller scopes at enqueue time, preserved for recovery replay. */
   gatewayClientScopes?: readonly string[];
 };
@@ -144,6 +147,7 @@ export async function enqueueDelivery(
     forceDocument: params.forceDocument,
     silent: params.silent,
     mirror: params.mirror,
+    session: params.session,
     gatewayClientScopes: params.gatewayClientScopes,
     retryCount: 0,
   });

src/infra/outbound/delivery-queue.recovery.test.ts

@@ -165,6 +165,15 @@ describe("delivery-queue recovery", () => {
           text: "a",
           mediaUrls: ["https://example.com/a.png"],
         },
+        session: {
+          key: "agent:main:main",
+          agentId: "agent-main",
+          requesterAccountId: "acct-1",
+          requesterSenderId: "sender-1",
+          requesterSenderName: "Sender One",
+          requesterSenderUsername: "sender.one",
+          requesterSenderE164: "+15551234567",
+        },
       },
       tmpDir(),
     );
@@ -183,6 +192,15 @@ describe("delivery-queue recovery", () => {
           text: "a",
           mediaUrls: ["https://example.com/a.png"],
         },
+        session: {
+          key: "agent:main:main",
+          agentId: "agent-main",
+          requesterAccountId: "acct-1",
+          requesterSenderId: "sender-1",
+          requesterSenderName: "Sender One",
+          requesterSenderUsername: "sender.one",
+          requesterSenderE164: "+15551234567",
+        },
       }),
     );
   });

src/infra/outbound/delivery-queue.storage.test.ts

@@ -33,6 +33,12 @@ describe("delivery-queue storage", () => {
             text: "hello",
             mediaUrls: ["https://example.com/file.png"],
           },
+          session: {
+            key: "agent:main:main",
+            agentId: "agent-main",
+            requesterAccountId: "acct-1",
+            requesterSenderId: "sender-1",
+          },
         },
         tmpDir(),
       );
@@ -53,6 +59,12 @@ describe("delivery-queue storage", () => {
           text: "hello",
           mediaUrls: ["https://example.com/file.png"],
         },
+        session: {
+          key: "agent:main:main",
+          agentId: "agent-main",
+          requesterAccountId: "acct-1",
+          requesterSenderId: "sender-1",
+        },
         retryCount: 0,
       });
       expect(entry.payloads).toEqual([{ text: "hello" }]);
@@ -169,6 +181,37 @@ describe("delivery-queue storage", () => {
       expect(entry.gatewayClientScopes).toEqual(["operator.write"]);
     });
 
+    it("persists session context for recovery replay", async () => {
+      const id = await enqueueTextDelivery(
+        {
+          channel: "telegram",
+          to: "2",
+          payloads: [{ text: "b" }],
+          session: {
+            key: "agent:main:main",
+            agentId: "agent-main",
+            requesterAccountId: "acct-1",
+            requesterSenderId: "sender-1",
+            requesterSenderName: "Sender One",
+            requesterSenderUsername: "sender.one",
+            requesterSenderE164: "+15551234567",
+          },
+        },
+        tmpDir(),
+      );
+
+      const entry = readQueuedEntry(tmpDir(), id);
+      expect(entry.session).toEqual({
+        key: "agent:main:main",
+        agentId: "agent-main",
+        requesterAccountId: "acct-1",
+        requesterSenderId: "sender-1",
+        requesterSenderName: "Sender One",
+        requesterSenderUsername: "sender.one",
+        requesterSenderE164: "+15551234567",
+      });
+    });
+
     it("backfills lastAttemptAt for legacy retry entries during load", async () => {
       const id = await enqueueTextDelivery({
         channel: "whatsapp",