I've long been dealing with the following problem: I'm using GNU Emacs (current 26.0.91, but the problem has existed for a long time before that) and Gnus to send mail. The relaying MTA uses greylisting when receiving mail for local accounts without authentication, but smtpmail.el cannot deal with the resulting temporary SMTP codes. I'd expect that it would retry with authentication, but doesn't. I've used the following snippet to fix this. Perhaps this (or something similar) can be used to fix this issue? Thanks. Rainer -- ----------------------------------------------------------------------------- Rainer Orth, Center for Biotechnology, Bielefeld University