Thank you Taylor for your response! The article you are speaking of is the article I referenced and is a great reference.
Like you, I keep thinking that I have set everything correctly to allow a Windows Outlook client to authenticate and send/receive mail from the Mountain Lion server, but it just is working since I upgraded to Mountain Lion.
The error I keep getting is a 504 5. 5. 2 <EI052014L33R1> error.
Any additional assistance is greatly appreciated.
Regarding Outlook. Can it receive, send or neither?
If the problem is sending, two things to look at.
- You are configured for port 587 which is TLS.
In outlook, select TLS (not SSL)
I prefer to enable port 465 which is SSL, this plays well with outlook.
To do so, you need to edit
Look for these lines
#465 inet n - n - - smtpd # -o smtpd_tls_wrappermode=yes # -o smtpd_sasl_auth_enable=yes # -o smtpd_client_restrictions=permit_sasl_authenticated,reject # -o milter_macro_daemon_name=ORIGINATING
Uncomment them all. DO NOT remove the space before the -o (its required)
sudo postfix reload
Make sure 465 is open in your router
587 = TLS
465 = SSL
- Look at your smtp logs, do you see helo errors when you try to send from Outlook?
If so, do this (good idea to do this for ANY installation)
smtpd_helo_restrictions = reject_non_fqdn_helo_hostname reject_invalid_helo_hostname
smtpd_helo_restrictions = permit_sasl_authenticated permit_mynetworkseject_non_fqdn_helo_hostname reject_invalid_helo_hostname
sudo postfix reload
If this doesn't solve the issue.
Please post whether this is a receiving or sending problem.
If receiving, post output of mailaccess.log(imap) log when you attempt to pickup mail
If sending, post output of your mail.log(smtp) when you try to send.
I suppose you already know it's best not to open ports that you don't need. A TCPdump might help you to see what's being called on...
Also you said router so I assume you are connecting to a WAN using a common Broadband provider. Don't rule out their making changes on their end so you can't send. It does happen, not likely but it does happen. They could have made some changes during the time you were adding your upgrade OS.
You might also try little snitch to assist in gleaning some additional information from the connections your computer tries to make. I use it often when trying to sort out what's making network calls.