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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 @hotmail.com 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?

Thanks.

Woo.

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1 Answer 1

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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: rdpslides.com/webresources/FAQ00035.htm –  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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