Public bug reported:

Binary package hint: evolution

If Evolution tries to connect to a SMTP server to send mail, and the
remote server closes the connection while Evolution is busy (for
example, if Evolution prompts the user for a password and the server
times out), then Evolution treats the disconnection as an AUTH failure
and will keep prompting the user for a password even though there's
nothing listening at the other end. The only way of getting the mail
sent is to press CANCEL and then try again with Send & Receive.

(Related issue: this workaround only works because Evolution retries
with the last password the user entered --- except Evolution knows that
the password is not valid because it thinks (incorrectly) that the
remote server rejected it. Should it retry at all or simply forget the
password?)

In this situation, Evolution should notice that the connection has been
lost and reestablish it. (It would also be polite to prompt the user for
the password *before* opening the connection, to avoid holding the
connection open for long periods of time --- a lot of SMTP servers these
days use very short timeouts as an antispam measure; the one I found
this bug on is set to five seconds.)

This is Evolution 2.22.3.1 on Heron.

** Affects: evolution (Ubuntu)
     Importance: Undecided
         Status: New

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SMTP AUTH does not properly detect if the remote server closes the connection
https://bugs.launchpad.net/bugs/254199
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