Interesting problem: The occasional email not being displayed in Outlook Inbox

Email Experts,

Please help us to find a resolution for the most annoying of problems.  Occasionally an email sent to will not appear in her Outlook Inbox, however it will show up on her iPhone.

We have set up a contact entry in ADUC for, set up an email forwarding rule to forward all incoming emails to the aforementioned contact address (see attached).

Now, I'm pretty confident that this MobileMe crap isn't the problem, however it serves to highlight the error(s) when what is in the Outlook Inbox doesn't tally up with what is on the handheld.

So far we've had reports from two users: and  With user1 appearing to suffer the most "missing" emails.  The emails are seemingly random, sent from inside the domain and from various external domains (three emails from the same address in one day!).  All other emails appear as normal.

We are using Exchange 2003 SP2 running on SBS2003 fully patched up to date.

Any thoughts on how best to begin troubleshooting this issue?
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I'm not quite sure about, what you have written.

You have an windows account with a mailbox.
You have changed the Exchange properties of this user to forward all mails to another external address, which is and deliver the mail to the mailbox as well as to the external address. Right? (This would be the correct setting).

What do you want to say with "We have set up a contact entry in ADUC for"??? A contact can not have a forward address, it is just a contact, which shows up in the address book...

Have you checked the user(s) junk email folders? That sounds like the most plausable situation. Outlook itself would flag the email as junk but the iPhone would see it as a regular old message.
techies123Author Commented:
Bembi - the email is forwarded to the external email address which appears in the GAL (the reason we created a contact object).

Srepphan - the emails are not landing in the Junk folder.  We thought there might be a client side rule in Outlook interfering - but have since disabled all rules in the users' Outlook profiles.
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Hmmm. Try enabling message tracking in Exchange. That may give you some insight. Are the messages available by connecting with OWA or POP? How about another user opening the mailbox?

I am trying to deduce whether the message is remaining in the Exchange database or being forwarded and deleted.
techies123Author Commented:
Srepphan - thanks for the suggestions. I'll enable tracking and explore OWA vs. Outlook in the morning. I'll update this thread tomorrow.

Appreciate your assistance so far!
OK, just for clear understanding. with a mailbox.
you setup a contact (lets say User1 (mobile)) with the mail address
Mails addressed to is routed to his own mailbox as well as to the contact.

Result is, either the contact or the mailbox get the mail.
Are we confirm so far?

My questions:
The mailbox account has only the mail address "", nothing more (SMTP)
The contact has only the mail address "", nothing more (SMTP)

Are the settings for the first name / Last name the same for both accounts?

Do you have additional users with the same configuration than above, which are working?

The following thought and experiences:

1.) There may be a little bit naming confusion as long as both users have the same email name in front of the domain. The exchange routing engine make a difference between the mail name and the domain. As external mails are sent via SMTP, internal mails are sent via X400 protocol.

Each user as well as each contact gets at least two addresses, one SMTP and one X400. There may be the fact, that the SMTP address may be different, but the X400 address is identical for the user mailbox and the associated contact. Please check the addresses in AD, which are assigned to these two accounts and make sure the X400 addresses are different.

2.) The routing engine checks the domain name and then identifies the user by the mail name. If the mail name (before the @) is the same, this may iritiate the routing engine.

3.) MS made some essential changes in AD and EXCH attributes with one of the service packs. For contacts, the AD property "targetAddress" is the relevant field for the recipient.  If this is an older account, I made the experience, that this value is not updated anymore, if the contact is created before one of the service pack levels.

Ways to check:
First at all, goto ESM, got to your mail queue and there stop all queues. Now send a mail to your user. The mail will reach the queue and hold there undtil to reenable the queue. Now enable each queue step by step to see, how the mail passes the different queues. At one point, the mail must splitt up into two mails, one for the local mailbox and one for the external address.

You may delete the contact and recreate a new one. Avoid using excacly the same values for first and lastname and check after creation, that all attributes (SMTP / X400 address) are different. You may try a different mail name if possible. i.e. and if possible, at least to find out the issue. You can also create a complete set of accounts for testing.

Repeat the steps above and see, if now the splitt up works.

Also check your recipient policy for your users. It makes sense to create two policies, one for mailbox users and another one for external contacts to avoid, that the contacts may get the same X400 addresses than internal users. Nevertheless you assign a dedicated SMTP address, the default recipient policy assigns also an X400 address.

techies123Author Commented:
Bembi - wow! Lots of food for thought there, thank you.

I've got lots of troubleshooting and fault-finding to do tomorrow, that's for sure!

I'll post an update tomorrow...
Note that x.400 addresses are only used in Exchange in versions 5.5 and prior.
techies123Author Commented:
From further research internally.

We've also had a another case reported where another user failed to receive in Outlook a simple email with a 19K Excel attachment. This user *does not* have any phone forwarding enabled or Outlook rules set.

Message tracking reports:-
SMTP Store Driver : Message delivered locally to store to
[This was also reported for the mail forwarding user on their missing email]

User cannot find the mail in Outlook. Viewing the mailbox via the Backup Exec Selection Tool on the Server also shows No Trace.

Very very puzzling.
Just check the queue flow as I described.
techies123Author Commented:
Sorry for the delay in posting but I've been waiting to get onsite. Thanks Bembi, checking mailflow shows splitting. Onsite today and I've pinned this down to cacheing. Turn off Exchange cacheing on the client I get the Mcafee test messages OK. Turning on cacheing again stops receipt and the the test messages disappear. Using Outlook 2007 SP1 so I naturally expected Kbase Article 968773 "Outlook 2007 cache users not seeing new emails in Outlook" to address the issue. Upgraded to Office 2007 SP2, rebooted, tried Outlook /cleanips but no change. Emails still disappear and none of the missing (hidden?) have re-appeared. I've now escalated this to PSS.
Have you tried to clear the local cache and to let Outlook to resync the offline cache?

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techies123Author Commented:
Eventually used Microsoft PSS as they had a free call available. This was a combination of 2 factors. There is a known bug in Outlook 2007 Sp1 not receiving mails in some circumstances when running in cached mode. Installing SP2 fixed this. Also some users had set auto-delete on all Junk mail received.
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