From 1c6217e572b62a0fe19751defad4338928617c06 Mon Sep 17 00:00:00 2001
From: "gpt-engineer-app[bot]"
 <159125892+gpt-engineer-app[bot]@users.noreply.github.com>
Date: Sat, 18 Apr 2026 01:01:25 +0000
Subject: [PATCH] Changes

Co-authored-by: renee-png <262607627+renee-png@users.noreply.github.com>
---
 src/routeTree.gen.ts                        |  9 --------
 supabase/functions/send-smtp-email/index.ts | 25 +++++++++++++++++++--
 2 files changed, 23 insertions(+), 11 deletions(-)

diff --git a/src/routeTree.gen.ts b/src/routeTree.gen.ts
index 71c92e2..026bfc4 100644
--- a/src/routeTree.gen.ts
+++ b/src/routeTree.gen.ts
@@ -805,12 +805,3 @@ const rootRouteChildren: RootRouteChildren = {
 export const routeTree = rootRouteImport
   ._addFileChildren(rootRouteChildren)
   ._addFileTypes<FileRouteTypes>()
-
-import type { getRouter } from './router.tsx'
-import type { createStart } from '@tanstack/react-start'
-declare module '@tanstack/react-start' {
-  interface Register {
-    ssr: true
-    router: Awaited<ReturnType<typeof getRouter>>
-  }
-}
diff --git a/supabase/functions/send-smtp-email/index.ts b/supabase/functions/send-smtp-email/index.ts
index 55f22e9..2f9787d 100644
--- a/supabase/functions/send-smtp-email/index.ts
+++ b/supabase/functions/send-smtp-email/index.ts
@@ -87,6 +87,13 @@ Deno.serve(async (req) => {
     if (settings.port === 465) useTls = true;
     else if (settings.port === 587 || settings.port === 25) useTls = false;
 
+    console.log("SMTP connecting", {
+      host: settings.host,
+      port: settings.port,
+      tls: useTls,
+      hasAuth: !!settings.username,
+    });
+
     const client = new SMTPClient({
       connection: {
         hostname: settings.host,
@@ -96,6 +103,8 @@ Deno.serve(async (req) => {
           ? { username: settings.username, password }
           : undefined,
       },
+      debug: { log: true, allowUnsecure: false, encodeLB: true, noStartTLS: false },
+      pool: { size: 1, timeout: 20_000 },
     });
 
     fromAddr = settings.from_name
@@ -112,7 +121,10 @@ Deno.serve(async (req) => {
     // dedupe
     bccList = Array.from(new Set(bccList));
 
-    await client.send({
+    console.log("SMTP sending", { from: fromAddr, to: toList, cc: ccList, bcc: bccList });
+
+    // Race the send against a timeout so we get a useful error instead of a silent hang
+    const sendPromise = client.send({
       from: fromAddr,
       to: toList,
       cc: ccList.length ? ccList : undefined,
@@ -122,7 +134,16 @@ Deno.serve(async (req) => {
       content: body.text ?? "auto",
       html: body.html,
     });
-    await client.close();
+    const timeoutPromise = new Promise((_, reject) =>
+      setTimeout(() => reject(new Error("SMTP send timed out after 25s")), 25_000),
+    );
+    await Promise.race([sendPromise, timeoutPromise]);
+    console.log("SMTP send OK");
+    try {
+      await client.close();
+    } catch (closeErr) {
+      console.warn("SMTP close error (non-fatal)", closeErr instanceof Error ? closeErr.message : closeErr);
+    }
 
     // Log success
     await admin.from("email_logs").insert({