I'm testing a new installation of an SMTP server under IIS. I am running Windows Server 2008 R2 Standard 64 bit. Enabling the SMTP feature installs IIS6 and sets up an smtp server within it.
I want to use this to relay SharePoint email to my Google Apps accounts. WSS3 is installed on the same server.
When I test it with telnet I see a few strange things:
When IIS is reset, the SMTP Virtual Server is stopped and I need to manually start it. Is this normal?
When I send mail using telnet, addresses I enter always cause an Invalid Address warning on the first try, but work subsequently. For example:
helo 250 sharepoint.company.local Hello [127.0.0.1] mail from: email@example.com 501 5.5.4 Invalid Address mail from: firstname.lastname@example.org 250 2.1.0 email@example.com....Sender OK rcpt to: firstname.lastname@example.org 501 5.5.4 Invalid Address rcpt to: email@example.com 250 2.1.5 firstname.lastname@example.org... Recipient ok DATA... etc
The test emails send successfully, but I am a bit puzzled as to why it behaves that way. Why are the email addresses not resolving first time?