Can't send attachments in Outlook 2003

Hi there,

Recently, one of my users has lost the ability to send email attachments in Outlook 2003. We have been working on this issue for several days to no avail. Here is what we have tried so far:

- Everything we have found on EE and on the Microsoft Support Web site
- Updating all service packs for both XP Pro and Office 2003
- Reinstalling Office completely Outlook alone
- Changing the location of delivered email, even starting from a new Outlook file
- Ensuring that no encryption is used, and trying it with compressible encryption (this seemed to help for a while)
- Verified that all setting are correct in the mail profile (ie, usernames and passwords, pop servers, smtp servers, etc)

Here are some of the other things I have noticed that might be helpful:
- Attachment size does not matter, just that there is an attachment
- Test settings works fine
- Sending regular (ie no attachments) mail works fine

We are really on the brink of reformatting these computers and starting over, so any insight or assistance would be deeply appreciated.

Who is Participating?
WadskiIT DirectorCommented:
Is there any antivirus or 3rd party content filtering in place in the company (Norton on PCs or Messagelabs type system)?
Does the email and attachment appear in the Sent Items folder with the attachment intact and viewable?
Do you use Exchange to distribute the mail?

Using the same username and password can the user send attached emails from another PC?
A.V.Lead EngineerCommented:
When you say "lost the ability to send email attachments" can you be more spefic?  Does thos task cause Ouitllok to crash and if so with what error or do you no longer have to option to insert attachments?  Thanks!
gwhisenantAuthor Commented:
"Lost the ability to send email attachments" = sometimes it works and sometimes it doesn't. Eventually, the attachments will go out, it seems, but sometimes it takes hours, and sometimes days. If it takes days, I'll get the call and will almost always delete the attachment in the course of trying to fix the problem.  Notably, there are about ten users with email account for this domain, and now two of them are having the problem. The other users' settings are the same, and are not having any trouble.

Outlook itself does not crash, them messages with attachments simply stay in the Outbox. If I try to troubleshoot, I will get an error message saying the Outlook has already started sending the item. If that happens, I take Outlook offline and delete the attachment as descrived in various articles on EE and MS Knowledge base.
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gwhisenantAuthor Commented:

1) There is no content filtering in place in the company at this time, and no antivirus, which has been removed while we work on this problem.
2) The email and attachment do not appear in Sent Items at all.
3) This email domain is not using Exchange. The local domain is SBS 2003 with AD/Exchange, however, this FQDN is not handled by Exchange. Instead it is handled through POP/SMTP on a Linux server with Sendmail.
4) Haven't tried your other suggestion, but will try it and post reply.
Hopefully im not breaking any rules.

gwhisenant, you posted a question (link below); i have the same issue; did you find out what was causing it?

gwhisenantAuthor Commented:
Detox1978 --

Yes, we resolved the issue. For us, it was that compression was being used on the user PCs. We exported to PST for all accounts, removed the account from the box, set it back up ensuring no method of compression, and it worked like a charm. We also replaced a hub and put in a switch, which improved the traffic flow but wasn't directly related to this issue.

Hope it works, and let me know if you have any other questions or if you want to pass along more symptoms of the issues you are experiencing.

gwhisenantAuthor Commented:
Not sure why there is a forced accept. The accepted answer did not resolve the issue.
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