Hey Experts, Ok, I have looked in the Imail help archive, Imail knowledge base, the ISA Server list message archive, http://www.isaserver.org, ISA Server SMTP Server Support article and tried the suggestions and have not found the solution that works. Test Environment, These Are Not Currently Production Machines: My firewall server is running MS 2000 Server, SP4, current with critical updates and patches, ISA Server 2000 SP1, Internal NIC, External NIC. My mail server on the inside NIC is running MS 2000 Server, SP4, current with critical updates and patches, IIS5, Ipswitch's I-mail server 8.02, two FQDN's setup for smtp, pop3 & http. My client machine on the internet MS 2000 Pro, SP4, current with critical updates and patches, Outlook 2002 XP, with the e-mail accounts outgoing server settings set to "my outgoing server (SMTP) requires authentication" Here's My SMTP Experience: Using my client machine I send an e-mail message from philja@xxxxxxxxxxxxxxx on the internal I-mail server to webmaster@xxxxxxxxxxxx a known working e-mail account on the internet and I receive the following bounced message: Your message did not reach some or all of the intended recipients. Subject: Sent: 8/15/2003 3:00 PM The following recipient(s) could not be reached: 'webmaster@xxxxxxxxxxxx' on 8/15/2003 3:00 PM 550 not local host prophoto.com, not a gateway I then look at the I-mail server logs and it shows the philja@xxxxxxxxxxxxxxx account not authenticating. I then look at the ISA 2000 Server application event viewer and it gives me the following error message. Event: 20031 Source: SMTPevt Description: an unknown SMTP command Data: AUTH LOG IN I can send a message from the webmaster@xxxxxxxxxxxx to the philja@xxxxxxxxxxxxxxx without issue. The "nslookup" information looks correct, the "netstat -na" info looks correct, I can telnet to the mail server without issue, I've tried secure mail publishing, SMTP server publishing rules and it is just not working. Here's My HTTP-Mail Experience: >From my client machine I attempt to logon to my I-mail account using my browser and http://mailhost.okcrecovery.com:8383 address and receive the following error message, "page cannot be displayed" So anyway, if someone has an idea of what I am doing wrong I would sure appreciate any help! Thanks, John