wrote:

I figured out what the problem was. FYI to anyone that sees this
problem:

The problem was that Outlook has a hidden folder that it uses for
temporary attachment storage. I found that Outlook has trouble when
there are 100 temporary files with the same name. Since we always
send out the files with the same name, it keeps creating temporary
files with the same name:

Well known issue that has been discussed many, many times in this newsgroup.
See
http://www.howto-outlook.com/faq/securetemp.htm
--
Brian Tillman