From ddf1cfd01a06ae78e0ceafecf105192d61d5655d Mon Sep 17 00:00:00 2001
From: Konstantin Wohlwend <n2d4xc@gmail.com>
Date: Mon, 28 Jul 2025 17:27:21 -0700
Subject: [PATCH] Improve email deliverability checks

---
 apps/backend/src/lib/config.tsx             |  2 +-
 apps/backend/src/lib/emails.tsx             | 22 +++++++++++++++++----
 apps/dashboard/src/app/background-shine.tsx |  4 ++--
 3 files changed, 21 insertions(+), 7 deletions(-)

diff --git a/apps/backend/src/lib/config.tsx b/apps/backend/src/lib/config.tsx
index 73c879ef5..7fde2e4e8 100644
--- a/apps/backend/src/lib/config.tsx
+++ b/apps/backend/src/lib/config.tsx
@@ -114,7 +114,7 @@ export function getProjectConfigOverrideQuery(options: ProjectOptions): RawQuery
         throw new StackAssertionError(`Expected 0 or 1 project config overrides for project ${options.projectId}, got ${queryResult.length}`, { queryResult });
       }
       if (queryResult.length === 0) {
-        throw new StackAssertionError(`Expected 1 project config override for project ${options.projectId}, got 0`, { queryResult, options });
+        throw new StackAssertionError(`Expected a project row for project ${options.projectId}, got 0`, { queryResult, options });
       }
       return queryResult[0].projectConfigOverride ?? {};
     },
diff --git a/apps/backend/src/lib/emails.tsx b/apps/backend/src/lib/emails.tsx
index a6e4e05ac..7bf88d034 100644
--- a/apps/backend/src/lib/emails.tsx
+++ b/apps/backend/src/lib/emails.tsx
@@ -59,9 +59,9 @@ async function _sendEmailWithoutRetries(options: SendEmailOptions): Promise<Resu
 }>> {
   let finished = false;
   runAsynchronously(async () => {
-    await wait(5000);
+    await wait(10000);
     if (!finished) {
-      captureError("email-send-timeout", new StackAssertionError("Email send took longer than 5s; maybe the email service is too slow?", {
+      captureError("email-send-timeout", new StackAssertionError("Email send took longer than 10s; maybe the email service is too slow?", {
         config: options.emailConfig.type === 'shared' ? "shared" : pick(options.emailConfig, ['host', 'port', 'username', 'senderEmail', 'senderName']),
         to: options.to,
         subject: options.subject,
@@ -78,7 +78,20 @@ async function _sendEmailWithoutRetries(options: SendEmailOptions): Promise<Resu
     if (options.emailConfig.type === 'shared' && emailableApiKey) {
       await traceSpan('verifying email addresses with Emailable', async () => {
         toArray = (await Promise.all(toArray.map(async (to) => {
-          const emailableResponse = await fetch(`https://api.emailable.com/v1/verify?email=${encodeURIComponent(options.to as string)}&api_key=${emailableApiKey}`);
+          const emailableResponseResult = await Result.retry(async (attempt) => {
+            const res = await fetch(`https://api.emailable.com/v1/verify?email=${encodeURIComponent(options.to as string)}&api_key=${emailableApiKey}`);
+            if (res.status === 249) {
+              const text = await res.text();
+              console.log('Emailable is taking longer than expected, retrying...', text, { to: options.to });
+              return Result.error(new Error("Emailable API returned a 249 error for " + options.to + ". This means it takes some more time to verify the email address. Response body: " + text));
+            }
+            return Result.ok(res);
+          }, 4, { exponentialDelayBase: 4000 });
+          if (emailableResponseResult.status === 'error') {
+            captureError("emailable-api-timeout", emailableResponseResult.error);
+            return to;
+          }
+          const emailableResponse = emailableResponseResult.data;
           if (!emailableResponse.ok) {
             throw new StackAssertionError("Failed to verify email address with Emailable", {
               to: options.to,
@@ -87,7 +100,8 @@ async function _sendEmailWithoutRetries(options: SendEmailOptions): Promise<Resu
             });
           }
           const json = await emailableResponse.json();
-          if (json.state === 'undeliverable') {
+          console.log('emailableResponse', json);
+          if (json.state === 'undeliverable' || json.disposable) {
             console.log('email not deliverable', to, json);
             return null;
           }
diff --git a/apps/dashboard/src/app/background-shine.tsx b/apps/dashboard/src/app/background-shine.tsx
index 599cc7b0d..42788baa6 100644
--- a/apps/dashboard/src/app/background-shine.tsx
+++ b/apps/dashboard/src/app/background-shine.tsx
@@ -24,8 +24,8 @@ export function BackgroundShine() {
         position: 'absolute',
         top: '-10%',
         left: '70%',
-        width: '20%',
-        height: '20%',
+        width: '20vw',
+        height: '20vh',
         background: 'linear-gradient(to bottom, #4E61B3, #9196F4)',
         borderRadius: '100%',
         filter: 'blur(100px)',