I use gmail with stunnel using Pegasus Mail with no problem using the special password. Pegasus has the Oauth options as well.. Gmail stunnel options I use (only use pop3 and smtp, just put imap) [gmailpop] client=yes accept = 127.0.0.1:20995 connect = pop.gmail.com:995 debug = 7 verifyChain = yes CApath = /etc/ssl/certs checkHost = pop.gmail.com OCSPaia = yes [gmailsmtp] client=yes accept = 127.0.0.1:20465 connect = smtp.gmail.com:465 debug = 7 verifyChain = yes CApath = /etc/ssl/certs checkHost = smtp.gmail.com OCSPaia = yes [gmailimap] client=yes accept = 127.0.0.1:20993 connect = imap.gmail.com:993 debug = 7 verifyChain = yes CApath = /etc/ssl/certs checkHost = imap.gmail.com OCSPaia = yes Pegasus just uses the local power with no ssl setup, so handles the ssl connection. Note this is a different password from regular password, and it you change regular gmail password need to recreate it as well. Hope that thelps. +------------------------------------------------------------+ Michael D. Setzer II - Computer Science Instructor (Retired) mailto:mikes@guam.net mailto:msetzerii@gmail.com mailto:msetzerii@gmx.com Guam - Where America's Day Begins G4L Disk Imaging Project maintainer http://sourceforge.net/projects/g4l/ +------------------------------------------------------------+