I currently have Active Directory, Exchange, POP3, and SMTP setup on a Windows 2003 Adv. Server. Webmail functions correctly. Retrieving email by POP3 works as it should. However, sending mail through SMTP from outlook will not work.
I have a firebox x500 with Filtered SMTP enabled. The correct IP address is selected and forwarded to the correct internal IP. I used filtered SMTP thinking that the proxied SMTP was causing the problems originally. However, nobody can send email while using outlook.
I tested using the Pear PHP Mail module and setting Auth to true while using an Active Directory/exchange mailbox username/password. And it works as intended.
For outlook: Ive tried using the IP address directly for the outgoing mail server with no luck. Under More Settings and Outgoing Server; I have tried every possible combination. Ive checked that it requires authentication, tried using same settings as incoming server, tried to log on using their username/password, and tried using their full email address/password for authentication. Nothing seems to work.
Is there a setting in outlook that I am missing or a setting in the SMTP server that I am missing?
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