Here's the telnet syntax, from a CMD prompt:
telnet <known-good-smtp-recipient-server (FQDN)> 25 [enter]
One good server to test with, and the full command is:
telnet cluster5out.us.messagelabs.com 25 [enter]
The approximate response from this server should be
220 server-7.tower-108.messagelabs.com ESMTP (some of the numbers in that return string may be different)
If you don't get that (if you get a .. cannot connect .. message or some such), you probably have an outgoing email port blocked, either within your network firewall, windows firewall, or it's being blocked by your ISP.
If you
do get a good response, then you should check SmarterMail further, and make sure, for one, that your Bindings have not changed.
This assumes that, as Matthew mentioned, you are not using an outgoing gateway; in this case you want to
telnet <gateway fully qualified domain name> 25 <enter> OR
telnet <gateway IP address> 25 <enter> from the CMD prompt.
Also, make sure you have no other SMTP servers running on that Windows server.
You can usually test your SM server's SMTP server directly with
telnet localhost 25 <enter>
(BTW you can then either close the command window or type quit [enter] to get back to the command prompt, leaving that command window open)
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Here's how to make sure your DNS settings are generally good (2 examples), from a CMD prompt:
ping cluster5out.us.messagelabs.com <enter> OR
ping mail.google.com<enter>
Any non-timeout response means your DNS settings should be OK.