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Does anyone know what might be causing the following situation?

Crontab emails are bouncing with the message "Message rejected as spam by Content Filtering." (I've contacted the mail server admin about this.)

But emails sent with the command "mail" etc. are "stat=Sent ... Queued mail for delivery" (according to the log), but never arrive and never bounce. I've tried sending as root and as other users.

Any help would be greatly appreciated! Thanks.

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up vote 0 down vote accepted

Well, you haven't really given us any good information to go on, but if I were to guess, the server sending the mails most likely doesn't have a proper DNS PTR (reverse) record. Have you tried instead of having that server deliver mail directly, having it send through a known-good smarthost instead?

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Yes, it looks like this was the problem. The (Windows) sysadmin didn't fix the reverse DNS problem, but did add my host's name to a whitelist, and now emails are being sent fine. Doesn't explain why root crontab emails were sending OK — but now things are working I haven't time to investigate! Thanks for your help. – Sam Wilson Aug 23 '10 at 4:59

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