🐛 Bug Report: SMTP not working with iCloud Mail #384

New Issue

OVERLORD · 2025-10-09T16:43:12+03:00

OVERLORD commented

2025-10-09 16:43:12 +03:00

Originally created by @etcg on GitHub.

Reproduction steps

I am using iCloud Mail with my own cloudflare domain, but I get an error in the log. I use these settings described here: https://support.apple.com/en-us/102525

Server name: smtp.mail.me.com
SSL/TLS Required: Yes
Port: 587
Username and password settings as described in the linked support document.

I tried several different ‘SMTP From’ email addresses. The same settings, as described, work with other self-hosted services. I also tried a test 'Email Login Notification' to rule out the possibility that the issue is related to the ‘Send test email’ function.

Expected behavior

Send mails.

Actual Behavior

With TLS enabled I get:

Error #01: failed to say hello to SMTP server: smtp: Hello called after other methods

With TLS unchecked this:

Error #01: failed to authenticate SMTP client: unencrypted connection

'Skip Certificate Verification' checked and unchecked makes no difference.

Version and Environment

v0.27.1

Log Output

[GIN] 2025/01/25 - 11:32:13 | 500 | 15.204531581s |     xxx.xxx.x.x | POST     "/api/application-configuration/test-email"
Error #01: failed to say hello to SMTP server: smtp: Hello called after other methods

Originally created by @etcg on GitHub. ### Reproduction steps I am using iCloud Mail with my own cloudflare domain, but I get an error in the log. I use these settings described here: https://support.apple.com/en-us/102525 - Server name: smtp.mail.me.com - SSL/TLS Required: Yes - Port: 587 - Username and password settings as described in the linked support document. I tried several different ‘**SMTP From**’ email addresses. The same settings, as described, work with other self-hosted services. I also tried a test '**Email Login Notification**' to rule out the possibility that the issue is related to the ‘**Send test email**’ function. ### Expected behavior Send mails. ### Actual Behavior With **TLS enabled** I get: ``Error #01: failed to say hello to SMTP server: smtp: Hello called after other methods`` With **TLS unchecked** this: `Error #01: failed to authenticate SMTP client: unencrypted connection` '**Skip Certificate Verification**' checked and unchecked makes no difference. ### Version and Environment v0.27.1 ### Log Output ``` [GIN] 2025/01/25 - 11:32:13 | 500 | 15.204531581s | xxx.xxx.x.x | POST "/api/application-configuration/test-email" Error #01: failed to say hello to SMTP server: smtp: Hello called after other methods ```

OVERLORD added the bug label 2025-10-09 16:43:12 +03:00

OVERLORD closed this issue

2025-10-09 16:43:13 +03:00

OVERLORD referenced this issue

2025-10-09 16:58:19 +03:00

[PR #384] [MERGED] chore(deps-dev): bump vite from 6.2.1 to 6.2.3 in /frontend in the npm_and_yarn group across 1 directory #846

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