I solved the issue. I will post the solution here for the people that have the same problem: 1) Need to compile mutt with SASL (and smtp and ssl, of course): ./configure --enable-pop --enable-imap --enable-smtp --with-sasl --with-ssl 2) Add the following to your .muttrc: set smtp_authenticators="plain" set smtp_url="smtp://user:password@xxxxxxxxxxxxxx:587/" set ssl_starttls set certificate_file=~/.mutt.certificates Luis.