Exchange Server 2010 not forwarding to external contact

We have one user in an organization that prefers to have his corporate exchange email account forwarded to his home iso
It has worked flawlessly for years

All of a sudden nothing forwards.   If we check his mailbox in OWA all mail resides in there including our inbound tests -- however nothing is forwarded

Today as a further test I added myself as a contact on his mailbox forwarder.  Same thing!   Nothing forwards.

What to do?
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Can he send at all? Is it delivering to both his inbox AND forwarding it to his external address? His mailbox may be full if so.
j-teksolutionsAuthor Commented:
I will check to see if he can send now.  It is set to deliver to both.
I will also check the mailbox size thanks!  keep you posted
Good luck!
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SeanSystem EngineerCommented:
Did he have a rule or was it forwarded to an external contact? is the contact still there? It is possible that the rule got removed or the contact got removed depending on how the forward is setup.
j-teksolutionsAuthor Commented:
Ok guys update here

1.  User can send mail - emailed myself from his OWA
2.  Mailbox is not full - i even turned off the defaults for now for quota
3.  User has a contact in AD with mail flow settings pointing to external account
SeanSystem EngineerCommented:
in his mailbox settings make sure you have the forward pointed to that contact. I would also run a mail trace to see if its getting blocked somewhere. Sometimes junk email can stop this.
j-teksolutionsAuthor Commented:
Ok I have made sure I am the contact - email is correct for this test
I have made sure in Mail Flow Settings everything is set to forward to my contact and mailbox
Still no go
How do I run the trace?
j-teksolutionsAuthor Commented:
Oh I have made sure there are NO mailbox rules either
SeanSystem EngineerCommented:
here is how to trace the mail message using powershell. There is also a way to do it in OWA by going into the sent items and right clicking the message there should be a delivery report option.
Does message tracking give any clues?

Are there any transport rules enabled on the Exchange server?
Also, just check his AD account isn't locked or his password expired...... Not sure if that would interfere in this process but worth checking if tracking or tracing gives no clues.
j-teksolutionsAuthor Commented:
OK update - AD is all fine for the account
Now - stupid question maybe but - is the forwarding out to external contact inserted into his sent items?   I thought this was transparent and happens server side?
SeanSystem EngineerCommented:
you would be looking at your test message to his email address. you are correct it is transparent. so the message you sent to the user is the one you want to trace.
j-teksolutionsAuthor Commented:
Ok my sent test shows submitted and ok it appears - now it does deliver every time instantly to his inbox I have his OWA open and watch.   It just doesn't forward out to my external contact?
SeanSystem EngineerCommented:
can you send a test message directly to the contact?
As above, and also did you check the server yet for any transport rules?
And does message tracking on the Exchange server show an attempt to send to the contact at all?
j-teksolutionsAuthor Commented:
Yes the contact is me for this test - I don't have access to the users iPhone so I figured I will sub myself in to resolve this - I also did this because I wanted to rule out something with his account.  I have the same behaviour no forwards to me.

I will look for transport rules - what concerns me is it was always working with no server config or changes these are brutal to t shoot
SeanSystem EngineerCommented:
I would try to remove the contact and create a new one just to be 100% sure there isn't something messed up with that contact.
Yeah so check message tracking on the server. See whether it shows failed or anything like that. Also check the message queue on the server and see if there's anything stuck?

Do you send out through a smart host?

Can you send your external address an email directly from your internal company mailbox?
j-teksolutionsAuthor Commented:
Ok possibly some headway here

I deleted my contact in AD then re created it

Exchange does not see the contact to forward to ???
Its sitting in the master USERS container in AD
I have restarted all exchange services and still you cannot see or search tool find my contact?
This is not normal I assume?
SeanSystem EngineerCommented:
your creating the contact in AD first? I would create it in exchange and skip the AD creation...this makes sure it has the correct email settings already.
j-teksolutionsAuthor Commented:
Issue resolved.   PTR record and reverse DNS problem with the registrar.

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j-teksolutionsAuthor Commented:
In this case one of our techs spent time tracking end to end and discovered with the registrar a PTR record was missing
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