sendemail with gmail says connection refused

Question

I am trying to send an rmail with sendemail. installed via macports. What is wrong in the following and how do I go about fixing it?

bash-3.2$ sendemail -f [email protected] -u files -m message -t [email protected] -s smtp.gmail.com -a ~/temp/folder/*pdf
Jan 31 01:49:43 mycomp sendemail[10391]: ERROR => Connection attempt to smtp.gmail.com:25 failed: IO::Socket::INET: connect: Connection refused

Answer 1

Gmail wont accept connection without TLS support and the specific port 587 for it. Read it here. Execute the following -

sendemail -f [email protected] -u files -m message -t [email protected] -s smtp.gmail.com:587 -o tls=yes -a ~/temp/folder/*pdf

If this doesn't work, then provide your SMTP username and password with -xu and -xp options respectively.

Answer 2

I had faced the same issue and could resolve it. You can use the tls auto, 587 port command. Able to successfully send an email using Gmail SMTP.

sendemail -f "[email protected]" -u "Re : Alerts Script" -t "$EMAILS" -s "smtp.gmail.com:587" -o tls=auto -xu "[email protected]" -xp "Password" -m "$Msg"

Also, you have to apply couple of settings in Gmail.

1. Enable IMAP
2. Allow less secure app
3. Review suspicious activity and mark 'That's me' to allow communication.