I send emails with C-x m and AFAIK everything is configured OK. However, recently I got this response when I wanted to send an email:

smtpmail-send-it: Sending failed: 535 5.7.8 Error: authentication failed: Connection lost to authentication server in response to AUTH PLAIN <long hash here>

My second attempt resulted in (from *Messages*):

Sending via mail...
Sending email
Sending email done

Now I have two questions:

  1. Why did it fail the first time?

  2. Can I be sure that my email has been sent after all?

Update: through experiments I've discovered the following:

  1. This happens when title of email is written using Cyrillic script;

  2. Email is delivered anyway on second attempt.

Seems it's sort of bug, but I will wait for additional clarification.

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