Missing email?

I have a very strange problem that happens once in a while with a specific user. So far it's happened a couple of times.
This user has his mailbox configured to forward all emails to an outside address AND leave a copy in the mailbox.
This works 99% of the time, except that a couple of times the user has received the email in his external account, (a personal account) and NOT in his mailbox.
The exchange logs show NO trace of the email ever being sent to that user.
Today I received an email that had this user in the CC field, but he didn't get it in his mailbox.
When searching exchange, I see the email that came to me, but in the recipient field in the logs it only shows my name.
This is very strange and I have no explanation to give this user.
How can this be? How can exchange forward the email, show the CC in my email and not show this mailbox receiving this email?

Thank you so much for any ideas you can have as I am stumped.

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He was not able to receive mails in his Outlook..?
If yes, this may be because rules.

Also confirm whether he was getting mails in OWA or not.

You may like to read the article:

Probably it has your solution.

Thank you
amenezes0617Author Commented:
Thanks for the ideas, but none of this is the case. The email isn't going to the user's mailbox at all.
It doesn't show in the exchange logs at all. The user is using Outlook for MAC, and it DOES NOT show in OWA either.
If I could see it in the logs I would think it's a client issue, and I would probably find it in OWA, but that is not the case.

Any other ideas?

Thanks a lot.
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amenezes0617Author Commented:
Madan SharmaConsultantCommented:
your issue is bit confusing but I'll advise you please check his mail id in those mails which are received on the outside address and not received on exchange. May those mails are directly sent on his outside addresses not on his exchange ID's. This confusion can be happen due same Display name on both ID's
amenezes0617Author Commented:
Well, the display name is the same, on the user and on the contact, I changed it but since this has only happened twice I won't know if this helps or not for a while.
It's a very strange problem indeed, because I would expect to see in the exchange logs the mail being forwarded even if I don't see it going into the mailbox. But the logs show NOTHING going to that user or that contact at all, even though the person got it on the external address.

Thanks a lot.
Madan SharmaConsultantCommented:
Just once disable the mail forward for his mail for testing purpose only and create rule in outlook for forward mails to external email address. In this way mails will be only forward after delivering to the mailbox. and I think this will be better way to find out the exact issue..

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amenezes0617Author Commented:
Thanks, it will be tough to know if anything works or not.
Thanks for the help.
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