diff --git a/src/commands/agent/delivery.ts b/src/commands/agent/delivery.ts
index 32335c902..bc3ac2985 100644
--- a/src/commands/agent/delivery.ts
+++ b/src/commands/agent/delivery.ts
@@ -10,8 +10,10 @@ import {
   normalizeOutboundPayloads,
   normalizeOutboundPayloadsForJson,
 } from "../../infra/outbound/payloads.js";
-import { resolveAgentDeliveryPlan } from "../../infra/outbound/agent-delivery.js";
-import { resolveOutboundTarget } from "../../infra/outbound/targets.js";
+import {
+  resolveAgentDeliveryPlan,
+  resolveAgentOutboundTarget,
+} from "../../infra/outbound/agent-delivery.js";
 import type { RuntimeEnv } from "../../runtime.js";
 import { isInternalMessageChannel } from "../../utils/message-channel.js";
 import type { AgentCommandOpts } from "./types.js";
@@ -51,17 +53,21 @@ export async function deliverAgentCommandResult(params: {
   const targetMode =
     opts.deliveryTargetMode ?? deliveryPlan.deliveryTargetMode ?? (opts.to ? "explicit" : "implicit");
   const resolvedAccountId = deliveryPlan.resolvedAccountId;
-  const resolvedTarget =
+  const resolved =
     deliver && isDeliveryChannelKnown && deliveryChannel
-      ? resolveOutboundTarget({
-          channel: deliveryChannel,
-          to: deliveryPlan.resolvedTo,
+      ? resolveAgentOutboundTarget({
           cfg,
-          accountId: resolvedAccountId,
-          mode: targetMode,
+          plan: deliveryPlan,
+          targetMode,
+          validateExplicitTarget: true,
         })
-      : null;
-  const deliveryTarget = resolvedTarget?.ok ? resolvedTarget.to : undefined;
+      : {
+          resolvedTarget: null,
+          resolvedTo: deliveryPlan.resolvedTo,
+          targetMode,
+        };
+  const resolvedTarget = resolved.resolvedTarget;
+  const deliveryTarget = resolved.resolvedTo;
 
   const logDeliveryError = (err: unknown) => {
     const message = `Delivery failed (${deliveryChannel}${deliveryTarget ? ` to ${deliveryTarget}` : ""}): ${String(err)}`;
diff --git a/src/gateway/server-methods/agent.ts b/src/gateway/server-methods/agent.ts
index 33c2d7b10..51f8efe95 100644
--- a/src/gateway/server-methods/agent.ts
+++ b/src/gateway/server-methods/agent.ts
@@ -8,8 +8,10 @@ import {
   updateSessionStore,
 } from "../../config/sessions.js";
 import { registerAgentRunContext } from "../../infra/agent-events.js";
-import { resolveAgentDeliveryPlan } from "../../infra/outbound/agent-delivery.js";
-import { resolveOutboundTarget } from "../../infra/outbound/targets.js";
+import {
+  resolveAgentDeliveryPlan,
+  resolveAgentOutboundTarget,
+} from "../../infra/outbound/agent-delivery.js";
 import { defaultRuntime } from "../../runtime.js";
 import { resolveSendPolicy } from "../../sessions/send-policy.js";
 import { normalizeSessionDeliveryFields } from "../../utils/delivery-context.js";
@@ -218,14 +220,14 @@ export const agentHandlers: GatewayRequestHandlers = {
 
     if (!resolvedTo && isDeliverableMessageChannel(resolvedChannel)) {
       const cfg = cfgForAgent ?? loadConfig();
-      const fallback = resolveOutboundTarget({
-        channel: resolvedChannel,
+      const fallback = resolveAgentOutboundTarget({
         cfg,
-        accountId: resolvedAccountId,
-        mode: "implicit",
+        plan: deliveryPlan,
+        targetMode: "implicit",
+        validateExplicitTarget: false,
       });
-      if (fallback.ok) {
-        resolvedTo = fallback.to;
+      if (fallback.resolvedTarget?.ok) {
+        resolvedTo = fallback.resolvedTo;
       }
     }
 
diff --git a/src/infra/outbound/agent-delivery.test.ts b/src/infra/outbound/agent-delivery.test.ts
new file mode 100644
index 000000000..c1e752cf1
--- /dev/null
+++ b/src/infra/outbound/agent-delivery.test.ts
@@ -0,0 +1,80 @@
+import { describe, expect, it, vi } from "vitest";
+
+const mocks = vi.hoisted(() => ({
+  resolveOutboundTarget: vi.fn(() => ({ ok: true as const, to: "+1999" })),
+}));
+
+vi.mock("./targets.js", async () => {
+  const actual = await vi.importActual<typeof import("./targets.js")>("./targets.js");
+  return {
+    ...actual,
+    resolveOutboundTarget: mocks.resolveOutboundTarget,
+  };
+});
+
+import type { ClawdbotConfig } from "../../config/config.js";
+import { resolveAgentDeliveryPlan, resolveAgentOutboundTarget } from "./agent-delivery.js";
+
+describe("agent delivery helpers", () => {
+  it("builds a delivery plan from session delivery context", () => {
+    const plan = resolveAgentDeliveryPlan({
+      sessionEntry: {
+        deliveryContext: { channel: "whatsapp", to: "+1555", accountId: "work" },
+      },
+      requestedChannel: "last",
+      explicitTo: undefined,
+      accountId: undefined,
+      wantsDelivery: true,
+    });
+
+    expect(plan.resolvedChannel).toBe("whatsapp");
+    expect(plan.resolvedTo).toBe("+1555");
+    expect(plan.resolvedAccountId).toBe("work");
+    expect(plan.deliveryTargetMode).toBe("implicit");
+  });
+
+  it("resolves fallback targets when no explicit destination is provided", () => {
+    const plan = resolveAgentDeliveryPlan({
+      sessionEntry: {
+        deliveryContext: { channel: "whatsapp" },
+      },
+      requestedChannel: "last",
+      explicitTo: undefined,
+      accountId: undefined,
+      wantsDelivery: true,
+    });
+
+    const resolved = resolveAgentOutboundTarget({
+      cfg: {} as ClawdbotConfig,
+      plan,
+      targetMode: "implicit",
+    });
+
+    expect(mocks.resolveOutboundTarget).toHaveBeenCalledTimes(1);
+    expect(resolved.resolvedTarget?.ok).toBe(true);
+    expect(resolved.resolvedTo).toBe("+1999");
+  });
+
+  it("skips outbound target resolution when explicit target validation is disabled", () => {
+    const plan = resolveAgentDeliveryPlan({
+      sessionEntry: {
+        deliveryContext: { channel: "whatsapp", to: "+1555" },
+      },
+      requestedChannel: "last",
+      explicitTo: "+1555",
+      accountId: undefined,
+      wantsDelivery: true,
+    });
+
+    mocks.resolveOutboundTarget.mockClear();
+    const resolved = resolveAgentOutboundTarget({
+      cfg: {} as ClawdbotConfig,
+      plan,
+      targetMode: "explicit",
+      validateExplicitTarget: false,
+    });
+
+    expect(mocks.resolveOutboundTarget).not.toHaveBeenCalled();
+    expect(resolved.resolvedTo).toBe("+1555");
+  });
+});
diff --git a/src/infra/outbound/agent-delivery.ts b/src/infra/outbound/agent-delivery.ts
index adde8ee24..34db4042d 100644
--- a/src/infra/outbound/agent-delivery.ts
+++ b/src/infra/outbound/agent-delivery.ts
@@ -9,7 +9,9 @@ import {
   normalizeMessageChannel,
   type GatewayMessageChannel,
 } from "../../utils/message-channel.js";
-import { resolveSessionDeliveryTarget, type SessionDeliveryTarget } from "./targets.js";
+import { resolveOutboundTarget, resolveSessionDeliveryTarget, type SessionDeliveryTarget } from "./targets.js";
+import type { ClawdbotConfig } from "../../config/config.js";
+import type { OutboundTargetResolution } from "./targets.js";
 
 export type AgentDeliveryPlan = {
   baseDelivery: SessionDeliveryTarget;
@@ -86,3 +88,45 @@ export function resolveAgentDeliveryPlan(params: {
     deliveryTargetMode,
   };
 }
+
+export function resolveAgentOutboundTarget(params: {
+  cfg: ClawdbotConfig;
+  plan: AgentDeliveryPlan;
+  targetMode?: ChannelOutboundTargetMode;
+  validateExplicitTarget?: boolean;
+}): {
+  resolvedTarget: OutboundTargetResolution | null;
+  resolvedTo?: string;
+  targetMode: ChannelOutboundTargetMode;
+} {
+  const targetMode =
+    params.targetMode ??
+    params.plan.deliveryTargetMode ??
+    (params.plan.resolvedTo ? "explicit" : "implicit");
+  if (!isDeliverableMessageChannel(params.plan.resolvedChannel)) {
+    return {
+      resolvedTarget: null,
+      resolvedTo: params.plan.resolvedTo,
+      targetMode,
+    };
+  }
+  if (params.validateExplicitTarget !== true && params.plan.resolvedTo) {
+    return {
+      resolvedTarget: null,
+      resolvedTo: params.plan.resolvedTo,
+      targetMode,
+    };
+  }
+  const resolvedTarget = resolveOutboundTarget({
+    channel: params.plan.resolvedChannel,
+    to: params.plan.resolvedTo,
+    cfg: params.cfg,
+    accountId: params.plan.resolvedAccountId,
+    mode: targetMode,
+  });
+  return {
+    resolvedTarget,
+    resolvedTo: resolvedTarget.ok ? resolvedTarget.to : params.plan.resolvedTo,
+    targetMode,
+  };
+}