diff --git a/src/commands/agent.delivery.test.ts b/src/commands/agent.delivery.test.ts
index baa44213ab4..e13cf219966 100644
--- a/src/commands/agent.delivery.test.ts
+++ b/src/commands/agent.delivery.test.ts
@@ -48,6 +48,7 @@ describe("deliverAgentCommandResult", () => {
 
   async function runDelivery(params: {
     opts: Record<string, unknown>;
+    outboundSession?: { key?: string; agentId?: string };
     sessionEntry?: SessionEntry;
     runtime?: RuntimeEnv;
     resultText?: string;
@@ -62,6 +63,7 @@ describe("deliverAgentCommandResult", () => {
       deps,
       runtime,
       opts: params.opts as never,
+      outboundSession: params.outboundSession,
       sessionEntry: params.sessionEntry,
       result,
       payloads: result.payloads,
@@ -234,6 +236,30 @@ describe("deliverAgentCommandResult", () => {
     );
   });
 
+  it("uses caller-provided outbound session context when opts.sessionKey is absent", async () => {
+    await runDelivery({
+      opts: {
+        message: "hello",
+        deliver: true,
+        channel: "whatsapp",
+        to: "+15551234567",
+      },
+      outboundSession: {
+        key: "agent:exec:hook:gmail:thread-1",
+        agentId: "exec",
+      },
+    });
+
+    expect(mocks.deliverOutboundPayloads).toHaveBeenCalledWith(
+      expect.objectContaining({
+        session: expect.objectContaining({
+          key: "agent:exec:hook:gmail:thread-1",
+          agentId: "exec",
+        }),
+      }),
+    );
+  });
+
   it("prefixes nested agent outputs with context", async () => {
     const runtime = createRuntime();
     await runDelivery({
diff --git a/src/commands/agent.test.ts b/src/commands/agent.test.ts
index 3da6935b8ef..038e9651777 100644
--- a/src/commands/agent.test.ts
+++ b/src/commands/agent.test.ts
@@ -14,6 +14,7 @@ import { setActivePluginRegistry } from "../plugins/runtime.js";
 import type { RuntimeEnv } from "../runtime.js";
 import { createOutboundTestPlugin, createTestRegistry } from "../test-utils/channel-plugins.js";
 import { agentCommand } from "./agent.js";
+import * as agentDeliveryModule from "./agent/delivery.js";
 
 vi.mock("../agents/auth-profiles.js", async (importOriginal) => {
   const actual = await importOriginal<typeof import("../agents/auth-profiles.js")>();
@@ -49,6 +50,7 @@ const runtime: RuntimeEnv = {
 
 const configSpy = vi.spyOn(configModule, "loadConfig");
 const runCliAgentSpy = vi.spyOn(cliRunnerModule, "runCliAgent");
+const deliverAgentCommandResultSpy = vi.spyOn(agentDeliveryModule, "deliverAgentCommandResult");
 
 async function withTempHome<T>(fn: (home: string) => Promise<T>): Promise<T> {
   return withTempHomeBase(fn, { prefix: "openclaw-agent-" });
@@ -230,6 +232,35 @@ describe("agentCommand", () => {
     });
   });
 
+  it("forwards resolved outbound session context when resuming by sessionId", async () => {
+    await withTempHome(async (home) => {
+      const storePattern = path.join(home, "sessions", "{agentId}", "sessions.json");
+      const execStore = path.join(home, "sessions", "exec", "sessions.json");
+      writeSessionStoreSeed(execStore, {
+        "agent:exec:hook:gmail:thread-1": {
+          sessionId: "session-exec-hook",
+          updatedAt: Date.now(),
+          systemSent: true,
+        },
+      });
+      mockConfig(home, storePattern, undefined, undefined, [
+        { id: "dev" },
+        { id: "exec", default: true },
+      ]);
+
+      await agentCommand({ message: "resume me", sessionId: "session-exec-hook" }, runtime);
+
+      const deliverCall = deliverAgentCommandResultSpy.mock.calls.at(-1)?.[0];
+      expect(deliverCall?.opts.sessionKey).toBeUndefined();
+      expect(deliverCall?.outboundSession).toEqual(
+        expect.objectContaining({
+          key: "agent:exec:hook:gmail:thread-1",
+          agentId: "exec",
+        }),
+      );
+    });
+  });
+
   it("resolves resumed session transcript path from custom session store directory", async () => {
     await withTempHome(async (home) => {
       const customStoreDir = path.join(home, "custom-state");
diff --git a/src/commands/agent.ts b/src/commands/agent.ts
index 63741b559d0..9d869a0f5d1 100644
--- a/src/commands/agent.ts
+++ b/src/commands/agent.ts
@@ -59,6 +59,7 @@ import {
   emitAgentEvent,
   registerAgentRunContext,
 } from "../infra/agent-events.js";
+import { buildOutboundSessionContext } from "../infra/outbound/session-context.js";
 import { getRemoteSkillEligibility } from "../infra/skills-remote.js";
 import { normalizeAgentId } from "../routing/session-key.js";
 import { defaultRuntime, type RuntimeEnv } from "../runtime.js";
@@ -316,6 +317,11 @@ export async function agentCommand(
       sessionKey: sessionKey ?? opts.sessionKey?.trim(),
       config: cfg,
     });
+  const outboundSession = buildOutboundSessionContext({
+    cfg,
+    agentId: sessionAgentId,
+    sessionKey,
+  });
   const workspaceDirRaw = resolveAgentWorkspaceDir(cfg, sessionAgentId);
   const agentDir = resolveAgentDir(cfg, sessionAgentId);
   const workspace = await ensureAgentWorkspace({
@@ -461,6 +467,7 @@ export async function agentCommand(
         deps,
         runtime,
         opts,
+        outboundSession,
         sessionEntry,
         result,
         payloads,
@@ -809,6 +816,7 @@ export async function agentCommand(
       deps,
       runtime,
       opts,
+      outboundSession,
       sessionEntry,
       result,
       payloads,
diff --git a/src/commands/agent/delivery.ts b/src/commands/agent/delivery.ts
index af31d68ca6d..30ac335577a 100644
--- a/src/commands/agent/delivery.ts
+++ b/src/commands/agent/delivery.ts
@@ -16,7 +16,7 @@ import {
   normalizeOutboundPayloads,
   normalizeOutboundPayloadsForJson,
 } from "../../infra/outbound/payloads.js";
-import { buildOutboundSessionContext } from "../../infra/outbound/session-context.js";
+import type { OutboundSessionContext } from "../../infra/outbound/session-context.js";
 import type { RuntimeEnv } from "../../runtime.js";
 import { isInternalMessageChannel } from "../../utils/message-channel.js";
 import type { AgentCommandOpts } from "./types.js";
@@ -64,11 +64,12 @@ export async function deliverAgentCommandResult(params: {
   deps: CliDeps;
   runtime: RuntimeEnv;
   opts: AgentCommandOpts;
+  outboundSession: OutboundSessionContext | undefined;
   sessionEntry: SessionEntry | undefined;
   result: RunResult;
   payloads: RunResult["payloads"];
 }) {
-  const { cfg, deps, runtime, opts, sessionEntry, payloads, result } = params;
+  const { cfg, deps, runtime, opts, outboundSession, sessionEntry, payloads, result } = params;
   const deliver = opts.deliver === true;
   const bestEffortDeliver = opts.bestEffortDeliver === true;
   const turnSourceChannel = opts.runContext?.messageChannel ?? opts.messageChannel;
@@ -212,18 +213,13 @@ export async function deliverAgentCommandResult(params: {
   }
   if (deliver && deliveryChannel && !isInternalMessageChannel(deliveryChannel)) {
     if (deliveryTarget) {
-      const deliverySession = buildOutboundSessionContext({
-        cfg,
-        agentId: opts.agentId,
-        sessionKey: opts.sessionKey,
-      });
       await deliverOutboundPayloads({
         cfg,
         channel: deliveryChannel,
         to: deliveryTarget,
         accountId: resolvedAccountId,
         payloads: deliveryPayloads,
-        session: deliverySession,
+        session: outboundSession,
         replyToId: resolvedReplyToId ?? null,
         threadId: resolvedThreadTarget ?? null,
         bestEffort: bestEffortDeliver,