Exchange not sending emails with attachments

Hi All,

We have 3 exchange 5.5 SP 4 servers located in 3 different sites connected with site connectors not x.400, all 3 sites have Windows 2000 AD. The internet mail connector is located at head office. All 3 sites are connected via VPN.
Here is my issue; when a user at a site sends an email with both an external and internal email address with an attachment, they receive a bounce back only for the user at head office. The email will reach the external address and the other site. If they send the same email and remove the attachment everyone receives the email. Here is the error the sender receives (italics have been changed). There are plans for an upgrade to Exchange 2003.

head office user on 2011-02-04 11:37
            Unable to deliver the message due to a communications failure
      The MTS-ID of the original message is: c=US;a= ;p=location;l=server-110204183315Z-314
            MSEXCH:MSExchangeMTA:location:head office server

I have looked at solutions on EE and the majority point to DNS but I don't think it's a DNS issue because without the attachment everyone receives the email.

Any help would be appreciated.

Thanks in advance,
LVL 1
Noyan GonulsenAsked:
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davorinConnect With a Mentor Commented:
My attention was caught by your upgrade to exchange 2003 plan...

I think that your assumption is logical - that it is not DNS problem. (Double check that won't hurt)
I was thinking what are the differences when sending attachment. Certainly Antivirus software has more work to do. And maybe Antispam software also. Sometimes just disabling the software is not enough and only uninstall makes the difference. It is worth to try.
Do you have the same problem in all sites? Maybe you can also have VPN or internet connection problems and small mails don't have problems, because they are small enough to be sent between errors, while large mails get "damaged" on the way.
If you send a really small attachment do you still have the problems?
What about attachment type?

The installation is quite old, but the problems you got only recently. What have changed right before the problem arised?
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davorinCommented:
Here is one link with some suggestions:
http://www.tek-tips.com/viewthread.cfm?qid=323684

Are you using disclaimer? Try to disable it.
What about antivirus?

Also please reconsider your upgrading plans. Mainstream Support End Date for Exchange 2003 was in 2009. Extended support will last until 2014. In your place I would jump some versions and upgrade to version 2010 or at least to version 2007. I future you could have hard times to get support for 10-15 years old exchange server, because less and less people will be using it.
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Noyan GonulsenAuthor Commented:
Thanks for your reply Davorin.
I had already read that thread, I was searching EE and the net for a few days before I posted. EE was my last resort!
We are not using any disclaimers and I went through my antivirus settings (Symantec corp). Sorry, I should have clarified when I mentioned "resend the email" I meant compose a new message without the attachment and the recipients receive the email. The reason I mentioned Exchange 2003 is because I could not upgrade to 2010 from 5.5 as per Microsoft. I was going to plan a 2 phase upgrade to 2003 then 2010 (licensing is a killer).
Thanks again for your time, I appreciate it.
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Noyan GonulsenAuthor Commented:
Hi Davorin,

It's hard to determine when the problem started happening, I really can't say. It was brought to my attention a few weeks ago.
The size of the attachment doesn't seem to make a difference (1kb to 1mb) as soon as you add an external email address the email bounces back only from the head office recipients, the email will make it to the other locations and externally. If you remove the external email address everyone internally receives the email.
I will remove the antivirus and try again, I will let you know my findings

Thanks again,
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Noyan GonulsenAuthor Commented:
Hi Davorin,

I removed Symantec off the machine and I was able to send the emails with no issue, I preceded to redeploy the antivirus package back to the machine and tested again. It seems removing the antivirus worked! It just doesn't make any sense why sending to one branch works but not head office, nevertheless everything seems to be working.
Thanks again for your help and directing me in the right direction.
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davorinCommented:
I'm glad you have solved the problem.
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