🐛 Bug Report: SMTP not working with iCloud Mail #372

New Issue

OVERLORD · 2025-10-08T00:05:33+03:00

OVERLORD commented

2025-10-08 00:05:33 +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 2025-10-08 00:05:33 +03:00

OVERLORD closed this issue

2025-10-08 00:05:34 +03:00

OVERLORD commented

2025-10-08 00:05:35 +03:00

@etcg commented on GitHub:

I just wanted to confirm that it’s indeed working now. Thanks for the quick fix!

@etcg commented on GitHub: I just wanted to confirm that it’s indeed working now. Thanks for the quick fix!

OVERLORD commented

2025-10-08 00:05:36 +03:00

@stonith404 commented on GitHub:

This should be fixed in v0.27.2

@stonith404 commented on GitHub: This should be fixed in `v0.27.2`

OVERLORD commented

2025-10-08 00:05:36 +03:00

@kmendell commented on GitHub:

@etcg I think i may know the issue here not 100% though.

@stonith404 It looks like the Hello command is being called after some other email methods, if TLS is checked, which would go against the requirements of that function. If i have some time later today ill try to take a look at that.

Edit: Working on this now, I think i found a fix.

@kmendell commented on GitHub: @etcg I think i may know the issue here not 100% though. @stonith404 It looks like the Hello command is being called after some other email methods, if TLS is checked, which would go against the requirements of that function. If i have some time later today ill try to take a look at that. Edit: Working on this now, I think i found a fix.

OVERLORD referenced this issue

2025-10-08 00:18:25 +03:00

[PR #372] [MERGED] refactor: use atomic renames for uploaded files #852

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Reference: starred/pocket-id-pocket-id-1#372