diff --git a/CHANGELOG.md b/CHANGELOG.md
index a6899ebfa..920d789c7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,7 @@
 
 ## Unreleased
 
+- WhatsApp: route queued replies to the original sender instead of the bot's own number. (#534) — thanks @mcinteerj
 - Models: add OAuth expiry checks in doctor, expanded `models status` auth output (missing auth + `--check` exit codes). (#538) — thanks @latitudeki5223
 - Security: per-agent mention patterns and group elevated directives now require explicit mention to avoid cross-agent toggles.
 - Config: support inline env vars in config (`env.*` / `env.vars`) and document env precedence.
diff --git a/src/web/auto-reply.test.ts b/src/web/auto-reply.test.ts
index cf85f0414..55945741f 100644
--- a/src/web/auto-reply.test.ts
+++ b/src/web/auto-reply.test.ts
@@ -1132,6 +1132,44 @@ describe("web auto-reply", () => {
     expect(payload.Body).toContain("[from: Bob (+222)]");
   });
 
+  it("sets OriginatingTo to the sender for queued routing", async () => {
+    const sendMedia = vi.fn();
+    const reply = vi.fn().mockResolvedValue(undefined);
+    const sendComposing = vi.fn();
+    const resolver = vi.fn().mockResolvedValue({ text: "ok" });
+
+    let capturedOnMessage:
+      | ((msg: import("./inbound.js").WebInboundMessage) => Promise<void>)
+      | undefined;
+    const listenerFactory = async (opts: {
+      onMessage: (
+        msg: import("./inbound.js").WebInboundMessage,
+      ) => Promise<void>;
+    }) => {
+      capturedOnMessage = opts.onMessage;
+      return { close: vi.fn() };
+    };
+
+    await monitorWebProvider(false, listenerFactory, false, resolver);
+    expect(capturedOnMessage).toBeDefined();
+
+    await capturedOnMessage?.({
+      body: "hello",
+      from: "+15551234567",
+      to: "+19998887777",
+      id: "m-originating",
+      sendComposing,
+      reply,
+      sendMedia,
+    });
+
+    expect(resolver).toHaveBeenCalledTimes(1);
+    const payload = resolver.mock.calls[0][0];
+    expect(payload.OriginatingChannel).toBe("whatsapp");
+    expect(payload.OriginatingTo).toBe("+15551234567");
+    expect(payload.To).toBe("+19998887777");
+  });
+
   it("uses per-agent mention patterns for group gating", async () => {
     const sendMedia = vi.fn();
     const reply = vi.fn().mockResolvedValue(undefined);