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The simplest way to troubleshoot a mail problem is to go old school.
Do not enter stuff in parenthesis it's just for clarification)
- Make sure the Telnet client is installed on the server you are testing mail from
- enter the following commands
- telnet server port <enter> (for example telnet mymailserver 25)
- EHLO <enter> (yes it's EHLO)
- mail from:email@example.com <enter>
- rcpt to:firstname.lastname@example.org <enter>
- data <enter>
- this is my test message <enter.
- . <enter> (just a period and hit enter)
Either it will work and Nprinting will work or you will discover the problem.
- That server is unable to see mail server
- You have wrong port
- Mail server will not let you relay so sending internal email may work but not external
- Authentication errors with username/password. Just because it works in Exchange doesn't mean they allow SMTP for that account.