Docs for http://www.qmail.org/qmail-remote_authenticated_smtp.patch a patch to convince qmail-remote to use Authenticated SMTP when talking to certain hosts. This version of the patch has been modified by Robert Sanders so that base64 encoding of usernames and passwords is done automatically by qmail-remote. After applying the patch, the username password go into /var/qmail/control/smtproutes like so: domain:relay username password The domain:relay part is identical to a normal smtproutes entry (see the qmail-remote man page). For sites that require authentication, you simply add two space separated fields to the line, where the first field is the username, the second is the password. For example: inside.af.mil:firewall.af.mil:26 johndoe secret would send mail for inside.af.mil to firewall.af.mil, port 26 using username 'johndoe' and password 'secret' Since smtproutes will contain plain text usernames and passwords you might want to make the file owned by qmailr and set its permissions to 0600. Of course, the entries are going to go over the wire in the clear anyway as part of the SMTP transaction. Good luck. j.