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check that his reply too address is correct, my girlfriends work reply to address is wrong and I have to change it everytime I reply to an email from her!
It'll stop you sending mail out at all.. heh.
SMTP is port 25/TCP.. if it listens on anything else, it's broken. (I know AOL or something use some weird SMTP port going out.. but that's because they have some weird setup)
It'll just be getting delayed somewhere - they'll all turn up at some point probably.
I know BT only guarantee delivery within 4 days or similar, heh.