if you can telnet to the smtp port, have you tried to send an email manual by typing the message in the telnet window? If not you can do this this way, which will give you a more detailed view what went wrong sending mail:
Obviously telnet from your prtg server to your mailserver:
"telnet <yourmyilserver>"
You should get something like: " 220 * SMTP Server Ready"
Type "HELO test"
You shoud get: "250 Hello test, pleased to meet you"
Type "MAIL FROM: [email protected]"
You shoud get: "250 [email protected] OK"
Type "RCPT TO: "<your_destination_mailaddress>"
You shoud get: "250 <your_destination_mailaddress> ... Recipient ok"
Type "DATA"
You shoud get: "354 Start Mail input, end with <CRLF>.<CRLF>"
Type "SUBJECT: Telnet Test <CR>"
Lore ipsum...<CR>
<CR>
.<CR>
You shoud get: "250 OK"
after that your mail is send. if there is a break in the process described above, the returning SMTP code should give you more info on what went wrong.
You shoud get: "354 Start Mail input, end with <CRLF>.<CRLF>"
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