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At the moment we have a rule that limits SMTP traffic through TCP port 25. If I do a test email to a address the email doesn't arrive, nor are there any bouce-back errors. If I send from hotmail to our domain, then reply to that email, that works fine.

Is there some kind of SMTP filter option that I can check/change to allow hotmail addresses out?



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up vote 1 down vote accepted

What email server are you using? Are there any message tracking logs or SMTP logs? Have you tried to telnet to hotmail to send a test email?

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Exchange 2003. Yes I've checked the exchange logs and I'm not sure what to look for exactly in them. – The Woo Sep 15 '09 at 2:12
Make sure message tracking is turned on in ESM and make sure SMTP logging is enabled. Then send an email to a hotmail recipient and check the logs. They should give you some insight into what's happening. Also, if you make a telnet connection to port 25 of a hotmail server you can test basic ip connectivity and DNS resolution by sending an email through telnet. – joeqwerty Sep 15 '09 at 2:22
I haven't done much telnetting. What should I type in? – The Woo Sep 15 '09 at 2:36
From a command prompt type: telnet mx1.hotmailcom 25 The try sending an email to a valid hotmail address and see what responses you get from the hotmail server. Here's a brief rundown on how to send an email via telnet: – joeqwerty Sep 15 '09 at 2:45
Ok, so when I try to RCPT TO: <my email> it comes up with "550 Requested action not taken: mailbox unavailable" – The Woo Sep 15 '09 at 3:47

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