Some email not making it through sometimes, other times no problem

I have a user on my server who complains that sometimes she receives email from a particular person and sometimes not. She receives all other email just fine. I need help trying to diagnose why some of those messages just disappear.
In Server Admin, mail filtering is set to deliver spam, but change the subject line to include * SPAM * so my thought is the message should be arriving one way or another. I've set all logging levels to debug in the Mail services section. I searched through some log files looking for the particular email address, hoping to find a reason it was ignored sometimes, no luck.
Can someone help me find out why some messages from that outsider get delivered and sometimes not?
Thank you!!!
--Patrick

Check the client's mail tool (as was mentioned) for its spam filtering settings, and check the details of these lost or missing messages from the sender's end (eg: have the sender forward one of the lost messages to another user), and have the sender replicate the messages to another address for a while (other than to this user), and investigate the contents of the particular messages (to see if there's something tripping spam filtering), and investigate white-listing the sender for the particular client.
I'd also take a look at the version of the client's mail tool (for upgrades or fixes not covered by, for instance, Mac OS X upgrades), and at the configuration of the client system and the client mailer.
It's quite possible to set up message processing rules in most mail clients, and these can cause mail messages to appear lost if the rules are forgotten or miscoded.
It's possible that the mail is going into the bit-bucket at the sender's end of the connection. There are tools which scan out-bound SMTP messages in place at the firewall within some organizations. And there are buggy SMTP servers around. (Hence the earlier suggestion to replicate future messages to multiple receivers.)
Further down the chain of what most folks want to look at are the SMTP logs. Feasible, but somewhat more work than I'd want to start with.

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