Thanks Sahil, I actually had that attached but was getting bounced for too long of an email to the mailing list.
I ran "saslfinger -c" and did not receive any errors. The man pages indicated that it should also tell what type of connections the smtp server should accept however this did not seem to happen, though i could be mis-interpreting the output. Here is my postconf -n output: alias_database = hash:/etc/aliases alias_maps = hash:/etc/aliases command_directory = /usr/sbin config_directory = /etc/postfix daemon_directory = /usr/libexec/postfix debug_peer_level = 3 debug_peer_list = smtp.gmail.com home_mailbox = Maildir/ html_directory = no inet_interfaces = all mail_owner = postfix mailq_path = /usr/bin/mailq.postfix manpage_directory = /usr/share/man mydestination = $myhostname, localhost mydomain = powerdnn.com myhostname = monitor.powerdnn.com mynetworks_style = host myorigin = $mydomain newaliases_path = /usr/bin/newaliases.postfix queue_directory = /var/spool/postfix readme_directory = /usr/share/doc/postfix-2.3.3/README_FILES relay_domains = relayhost = [smtp.gmail.com]:587 sample_directory = /usr/share/doc/postfix-2.3.3/samples sendmail_path = /usr/sbin/sendmail.postfix setgid_group = postdrop smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd smtp_sasl_security_options = noanonymous smtp_sasl_tls_security_options = noanonymous smtp_tls_cert_file = /etc/pki/tls/gmail_relay/gmail.pem smtp_tls_enforce_peername = no smtp_tls_key_file = /etc/pki/tls/gmail_relay/gmail.key smtp_tls_note_starttls_offer = yes smtp_tls_scert_verifydepth = 5 smtp_use_tls = yes smtpd_tls_ask_ccert = yes smtpd_tls_req_ccert = no tls_random_source = dev:/dev/urandom unknown_local_recipient_reject_code = 550 -- Always glad to help, --Jay Bendon - Bendon Consults On Thu, Feb 11, 2010 at 7:23 PM, Sahil Tandon <sa...@tandon.net> wrote: > On Thu, 11 Feb 2010, Jay Bendon wrote: > >> Feb 11 18:23:18 nagios postfix/smtp[22559]: 261085EEB34: >> to=<jay.ben...@powerdnn.com>, relay=smtp.gmail.com[74.125.47.109]:587, >> delay=1040, delays=1039/0.03/0.57/0, dsn=4.7.0, status=deferred (SASL >> authentication failed; cannot authenticate to server >> smtp.gmail.com[74.125.47.109]: no mechanism available) > > Upon joining this mailing list, you were informed about DEBUG_README, a > document which contains guidelines for troubleshooting common problems > and asking for helping on this mailing list. As requested in that > document, please provide: > > Output from "postconf -n". Please do not send your main.cf file, or 500+ > lines of postconf output. > > If the problem is SASL related, consider including the output from the > saslfinger tool. This can be found at > http://postfix.state-of-mind.de/patrick.koetter/saslfinger/. > > -- > Sahil Tandon <sa...@tandon.net> >