So we had our local mail service that accepted STARTTLS on port 587, so in .mh_profile I had: send: -nomime -msgid -server auth.smtp.vt.edu -port 587 -tls -sasl and in .netrc I had: machine auth.smtp.vt.edu login valdis password dream-on-not-what-it-really-is and it Just Worked. We're starting a transition to Google Apps, and I got selected as a crash test dummy. So I fix .mh_profile to have '-server smtp.gmail.com' instead, and add to .netrc: machine auth.smtp.vt.edu login valdis password dream-on-not-really machine smtp.gmail.com login valdis(_at_)vt(_dot_)edu password dream-on-not-really and gmail wouldn't take it. Near as my testing shows, when send/post go to read .netrc, it doesn't use the '-server' value to look up 'machine' and then pick up the login/password fields - once I added '-user valdis(_at_)vt(_dot_)edu', it was then able to find the right line in .netrc and it started working. This is probably a bug, because it's quite possible that somebody could have the same 'userid' on multiple mail servers, but different passwords - so you really want to look up by machine, not login. (Heck, if our internal people had done things differently, it would have been 'login valdis(_at_)vt(_dot_)edu' on both SMTP servers).
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