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Sometimes delivery fails, often with the generic error message ‘Sending failed; SMTP protocol error’. Enabling one or both of the following variables and inspecting a trace buffer will often give clues to the reason for the error.
smtpmail-debug-infoThe variable smtpmail-debug-info controls
whether to print the SMTP protocol exchange in the
minibuffer, and retain the entire exchange in a buffer
*trace of SMTP session to server*,
where server is the name of the mail server to
which you send mail.
smtpmail-debug-verbThe variable smtpmail-debug-verb controls
whether to send the VERB token to the server.
The VERB server instructs the server to be more
verbose, and often also to attempt final delivery while your
SMTP session is still running. It is usually only useful
together with smtpmail-debug-info. Note that
this may cause mail delivery to take considerable time if the
final destination cannot accept mail.