Attachments get stripped from emails

Im at the end of my wits with this issue.  I have been troubleshooting this issue for 2 days now and now another user is experiencing this problem.  So please any expert advice is appreciated.

Our company is going through a merger so we have:
users on oldserver1.domain -- os1.domain(using 2003 exchange server)
users on oldserver2.domain -- os2.domain(using 2007 exchange server)
users on newserver.domain - ns.domain (using 2010 exchange server)
Clients use XP, 7.
Client use a mixture of outlook Outlook XP - Outlook 2007

One user received an email generated by another server with a PDF attachment.
User(Outlook XP) attempts to forward email with attachment (CONFIRMED IN USER's SENT BOX) to User2.
User 2(outlook 2007) receives email but no attachment.
User sends email with attachment to user (using forward method) to User3 and User3 receives email and attachment (outlook 2007)
User 3 sends email with attachment to user 2 and user 2 receives email with attachment.
This morning user1 can send attachments to user 2 and user 2 receives.
Attachments forward from user3 to user 2 are not received now.
Message original format is Plain Text to User1 and is sent as Plain Text.

Confirmed attchments are missing in OWA (Webmail)
Removed all temporary internet files associated with Outlook.
Configured user on a new system and setup and still no attachments with email.
Send email in all 3 different types of formats (rich text, HTML, plain)

Key Points:
U2 is on new domain
U1,3 is on old domain

U1 -X-> U2  U1 ---> U3 U3 --->2
U1 ---> U2 U1 ---> U3 U3 -X->2

If I save the attachment to my desktop / or send a file as an attachment regularly U2 gets the email plus attachment.
If forwarding the emails with appropraite formats user does not get attachment.

Any help is greatly appreciated.
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silentd3at4Author Commented:
The solution.  We were missing a key value in our Exchange 2010 EdgeTransport.exe configuration file (full path:  C:\Program Files\Microsoft\ Exchange Server\V14\Bin\)

What we had to do was open the config file EdgeTransport.exe.config (on one server it had the .config ext but the other it did not look for the Config file type before trying to edit.) and add the bottom of the list of keys (order mattered for some reason at the top it did not work) the following key:

<add key="TreatInlineDispositionAsAttachment" value="true" />

I suggest adding this to the file first before saving because you need to stop and start a service in Exchange for the changes to take effect. Therefore this minimizes the down time of your transport service.  

Go to services and stop the Exchange Management Transport service.  Then SAVE the config file and then start the Exchange Management Transport service.

Attachments started working fine BUT there is no paperclip symbol in Outlook or OWA.  When speaking to Microsoft they said there was nothing more they could do for me in this regard but at least the users are getting their attachments now.

Hope this helps someone else and saves someone a 6 hour call with Microsoft ROFL.
silentd3at4Author Commented:
When I forward email with PDF attachment she does not see attachment or attachment is gone.

When I forward email with attachment already there and then attach a file from my desktop to the email she sees both attachments not just the one from my desktop.
First try this: Close Outlook, click Start->Run, type Outlook /cleanprofile
If that doesn't do the trick then recreate the Outlook profile. Profile corruption is the source of many strange behaviours in Outlook.
You may first want to save away the address cache (the .nk2 file) which contains the addresses the user has prevoiusly sent successfully. You find the .nk2 file here (XP):
C:\Documents and Settings\<user>\Application Data\Microsoft\Outlook
(Vista / W7: C:\Users\{username}\AppData\Roaming\Microsoft\Outlook)
If you do not know how to recreate a profile:
After recreating the profile you can restore the .nk2 file to the same location assuming you used the same name for the new Outlook profile.
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silentd3at4Author Commented:
I appreciate the input peakpeak.  Those are two valid steps but neither worked.

I recreated a profile but still EVERY user is not receiving the attachment i Forward.
I also ran the Outlook /cleanprofile from the Run... (sorry i am using 7 on my system but there is a mix of 7 and XP on other systems)

I have tried a lot but I keep thinking it might be something server specific.  The original users who had this issue have not complained further but I still do not want to disregard the issue in case it appears later down the road.

So on that note any ideas where and what to check in the exchange server?  The current process our system uses (if understood correct) is old domain(od) user (odu) is trying to communicate to the new domain(nd) user (ndu).

odu -> od -> nd -> ndu

I believe it is an issue somewhere between the OD and the ND (just based off the rigorous testing I have done on the client side.
Checked the Group Policies om both domains? If nothing there then switch on Message Tracking (should always be on):

Message tracking 2003

Message tracking 2007

Message Tracking 2010

silentd3at4Author Commented:
If understood correctly.

Message tracking should only track the trail of the emails. (To and From) not the contents such as attachments would it?

The user's are receiving the emails but there is no record or note that there used to be an attachment.
Message tracking: If the sender is an internal user then search for "X-MS-Has-Attach: yes" under header .

If it is coming for the internet then check for Antivirus/Antispam policy settings

You didn't comment on Group Policy. Did you check that?
silentd3at4Author Commented:
I have not messed around with group policies on either of our exchange systems.  Would you mind putting me to some documents which would make me feel more comfortable in looking through this?

Was told that I could make some serious changes that would do some major damage if not aware of what I was looking at.

Thanks in advance.

I will update you soon on the Message Tracking status (overwhelmed with bunch of minor issues today at work but dont want them to pile up.)
silentd3at4Author Commented:
Here is the results from message tracker in the OD

 message tracking results
I see no line that mentions X-Ms-Has-Attach. (which it seems like the only time now that attachments are getting stripped is when the messages are coming from old domain users to new domain users.
silentd3at4Author Commented:
Intriguing ...

On the New Domain User's (NDU) system in Outlook / OWA there is an email (the forward) with no attachment when I right click the email go to options and read through the internet headers I see this:

 Internet Headers
silentd3at4Author Commented:
Had to sit on phone with Microsoft Tech Support for 6 hours to figure out the problem sharing my answer with the communicty.  PeakPeak got me off troubleshooting the clients and into looking at the server by checking the Internet Headers of the messages.
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