fix(channels): improve health metadata and reply diagnostics

extensions/whatsapp/src/auto-reply/monitor/inbound-dispatch.test.ts

@@ -118,6 +118,16 @@ function getCapturedDeliver() {
   )?.dispatcherOptions?.deliver;
 }
 
+function getCapturedOnError() {
+  return (
+    capturedDispatchParams as {
+      dispatcherOptions?: {
+        onError?: (err: unknown, info: { kind: "tool" | "block" | "final" }) => void;
+      };
+    }
+  )?.dispatcherOptions?.onError;
+}
+
 type BufferedReplyParams = Parameters<typeof dispatchWhatsAppBufferedReply>[0];
 
 function makeReplyLogger(): BufferedReplyParams["replyLogger"] {
@@ -704,6 +714,44 @@ describe("whatsapp inbound dispatch", () => {
     ).toBe(sendComposing);
   });
 
+  it("logs delivery failures from the shared dispatcher with WhatsApp context", async () => {
+    const replyLogger = {
+      info: vi.fn(),
+      warn: vi.fn(),
+      error: vi.fn(),
+      debug: vi.fn(),
+    } as BufferedReplyParams["replyLogger"];
+    const error = new Error("send failed");
+
+    await dispatchBufferedReply({
+      connectionId: "conn-1",
+      conversationId: "+15550001000",
+      msg: makeMsg({
+        id: "msg-1",
+        from: "+15550001000",
+        to: "+15550002000",
+        chatId: "15550001000@s.whatsapp.net",
+      }),
+      replyLogger,
+    });
+
+    getCapturedOnError()?.(error, { kind: "final" });
+
+    expect(replyLogger.error).toHaveBeenCalledWith(
+      {
+        err: error,
+        replyKind: "final",
+        correlationId: "msg-1",
+        connectionId: "conn-1",
+        conversationId: "+15550001000",
+        chatId: "15550001000@s.whatsapp.net",
+        to: "+15550001000",
+        from: "+15550002000",
+      },
+      "auto-reply delivery failed",
+    );
+  });
+
   it("updates main last route for DM when session key matches main session key", () => {
     const updateLastRoute = vi.fn();
 

extensions/whatsapp/src/auto-reply/monitor/inbound-dispatch.ts

@@ -56,6 +56,29 @@ type SenderContext = {
   e164?: string;
 };
 
+function logWhatsAppReplyDeliveryError(params: {
+  err: unknown;
+  info: { kind: ReplyLifecycleKind };
+  connectionId: string;
+  conversationId: string;
+  msg: WebInboundMsg;
+  replyLogger: ReturnType<typeof getChildLogger>;
+}) {
+  params.replyLogger.error(
+    {
+      err: params.err,
+      replyKind: params.info.kind,
+      correlationId: params.msg.id ?? null,
+      connectionId: params.connectionId,
+      conversationId: params.conversationId,
+      chatId: params.msg.chatId ?? null,
+      to: params.msg.from ?? null,
+      from: params.msg.to ?? null,
+    },
+    "auto-reply delivery failed",
+  );
+}
+
 function resolveWhatsAppDisableBlockStreaming(cfg: ReturnType<LoadConfigFn>): boolean | undefined {
   if (typeof cfg.channels?.whatsapp?.blockStreaming !== "boolean") {
     return undefined;
@@ -355,6 +378,16 @@ export async function dispatchWhatsAppBufferedReply(params: {
         }
       },
       onReplyStart: params.msg.sendComposing,
+      onError: (err, info) => {
+        logWhatsAppReplyDeliveryError({
+          err,
+          info,
+          connectionId: params.connectionId,
+          conversationId: params.conversationId,
+          msg: params.msg,
+          replyLogger: params.replyLogger,
+        });
+      },
     },
     replyOptions: {
       disableBlockStreaming,