Thank you for your post.
I don't have access to Windows Server 2008, so I have forwarded the information to our Software Quality Assurance (Testing) department for additional information.
Here is the latest from our Testers:
What SMTP Server are you using? That is, MS Exchange, SendMail, etc.
Determine if your connection is valid to the SMTP server.
From Windows 2003 (Windows 2008 install telnet from Add features Wizard), open the command prompt and type the following:
telnet mail.mailserver.xxx 25
MAIL FROM: email@example.com
Subject:-type <subject goes here->
type your message here (next line needs a dot then enter)
When done, check your email. If mail was sent to the address specified at RECPT TO: then the mail server is working and accepting mail from your domain on port 25.
If it did not work, then have the mail admin check for SMTP Authentication settings on the mail server and any relaying restrictions based on IP (your system IP with FileMaker Server installed).
1. If the SMTP server is set to use SMTP Authentication, enter user account name and password under SMTP Authentication.
2. Use standard port 25
3. Use test button "Test SMTP Settings"
For client based scripts
1. From the client side or via a FileMaker Pro database, enable the "Authentication" in the script to use either "Plain password" or "Cram-MD5" for the Authentication method.
Please keep me posted with your progress/outcome.