#2461 ✓cantreproduce
Doug Harrison

Failed to send message

Reported by Doug Harrison | December 8th, 2019 @ 07:47 PM

I've recently started receiving the following message for virtually all messages I try to send:

Failed to send message
Timeout during connect to "smtp.gmail.com" (465,465)

It continues to fail as long as I select Retry. When I click "Try Later" it seems to send fine 15 minutes later.

I've only noticed this within the last 3 days maybe - but it is now consistent. I can eventually get messages to go out, but they are not going out right away. This is not all emails...but is happening consistently.

I'm running MailMate 1.13.1.


Comments and changes to this ticket

  • benny

    benny December 9th, 2019 @ 02:24 PM

    It's strange that it eventually works and that could be a sign of a server issue. I don't have general Gmail error reports though. Try sending me a screenshot of your Gmail account settings using “Help > Send Feedback”. (You should use imap.gmail.com/smtp.gmail.com, the exact same username for both, default ports, and OAuth2 enabled.)

  • benny

    benny December 9th, 2019 @ 02:46 PM

    • State changed from “new” to “cantreproduce”

    Based on the settings it appears to be a temporary server issue.

  • Joachim

    Joachim June 15th, 2023 @ 03:21 PM

    Hi, I'm getting the same error:

    Timeout during connection to “smtp.gmail.com” (465,465).

    smtp works fine, but I cant send emails with smtp.gmail. Tried changing ports and disabling Oauth.

    telnet suggests an issue with the default URL

    telnet smtp.gmail.com 25
    telnet: connect to address Operation timed out
    Trying 2a00:1450:4025:401::6c...
    Connected to smtp.gmail.com.

    Any suggestions?


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