diff --git a/src/mailer.ts b/src/mailer.ts
index 1114471..35739a1 100644
--- a/src/mailer.ts
+++ b/src/mailer.ts
@@ -3,10 +3,13 @@ import { SMTP_HOST, SMTP_PORT, SMTP_USER, SMTP_PASSWORD, SMTP_FROM, MAILSHIP_NAM
 import type { Subscription } from './alert.js'
 import { render } from './templates.js'
 
+const secure = Number(SMTP_PORT) === 465
+
 const transporter = nodemailer.createTransport({
   host: SMTP_HOST,
   port: Number(SMTP_PORT),
-  secure: true,
+  secure,
+  requireTLS: !secure,
   auth: {
     user: SMTP_USER,
     pass: SMTP_PASSWORD,
@@ -16,28 +19,46 @@ const transporter = nodemailer.createTransport({
 export const sendConfirm = (sub: Subscription) => {
   const href = `${BASE_URL}/confirm?token=${sub.key}`
 
-  return transporter.sendMail({
-    from: SMTP_FROM,
-    to: sub.email,
-    subject: 'Confirm your email digest',
-    html: `
+  return transporter
+    .sendMail({
+      from: SMTP_FROM,
+      to: sub.email,
+      subject: 'Confirm your email digest',
+      html: `
       <h3>Welcome to ${MAILSHIP_NAME}!</h3>
       <p>Please confirm that you would like to receive ${sub.frequency} digests by clicking the link below:</p>
       <p><a href="${href}">Confirm Digest</a></p>
     `,
-    text: `Please confirm that you would like to receive ${sub.frequency} digests by visiting: ${href}`,
-  })
+      text: `Please confirm that you would like to receive ${sub.frequency} digests by visiting: ${href}`,
+    })
+    .catch(error => {
+      console.error('mailer: confirmation email failed', {
+        to: sub.email,
+        smtp: { host: SMTP_HOST, port: SMTP_PORT },
+        error: error?.message || error,
+      })
+      throw error
+    })
 }
 
 export const sendDigest = async (sub: Subscription, variables: Record<string, any>) => {
-  return transporter.sendMail({
-    from: SMTP_FROM,
-    to: sub.email,
-    subject: 'New activity',
-    html: await render('emails/digest.mjml', {
-      ...variables,
-      name: sub.email.split('@')[0],
-      unsubscribeUrl: `${BASE_URL}/unsubscribe?token=${sub.key}`,
-    }),
-  })
+  return transporter
+    .sendMail({
+      from: SMTP_FROM,
+      to: sub.email,
+      subject: 'New activity',
+      html: await render('emails/digest.mjml', {
+        ...variables,
+        name: sub.email.split('@')[0],
+        unsubscribeUrl: `${BASE_URL}/unsubscribe?token=${sub.key}`,
+      }),
+    })
+    .catch(error => {
+      console.error('mailer: digest email failed', {
+        to: sub.email,
+        smtp: { host: SMTP_HOST, port: SMTP_PORT },
+        error: error?.message || error,
+      })
+      throw error
+    })
 }
\ No newline at end of file
diff --git a/src/server.ts b/src/server.ts
index 8671380..204fb19 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -113,7 +113,10 @@ addRoute('post', '/subscription/email', async (req: Request, res: Response) => {
     const result = await registerSubscription({ pubkey, email, frequency })
     res.json(result)
   } catch (error: any) {
-    // If the error is just Postmark failing, the subscription was still created
+    // The subscription was still created, but sending the confirmation email
+    // may have failed. Always log it so SMTP issues are visible.
+    console.error('Failed to send confirmation email for', pubkey, error?.message || error)
+
     // Look up the actual subscription key from the DB
     const sub = await getSubscriptionByPubkey(pubkey)
     if (sub) {