This sometimes happens when the "handshake" that's supposed to signal the successful completion of the exchange fails to occur. And the problem is usually on the receiving end.

Sometimes a TOURBUS reader will send me an angry message asking why I sent them several hundred copies of the latest newsletter. In every case I've investigated, the LISTSERV machine only sent (or tried to send) one copy. Even though the message was delivered to the user's inbox, the mail server on the receiving end kept saying "I didn't get it, please resend."

This can happen if there is a bug in the mail delivery software, if there is a "mailbox full" or low disk space condition on the receiving end, or if the moon is full on a dark and stormy night.

There's not much you can do, except to ask the recipient to complain to their sysadmin or help desk, and hope they know how to fix the problem. Sending the file in multiple chunks might work, but that would require you to split up the original file into pieces and send each one separately. If you are concerned about the integrity of the document, this might not be a good idea. And depending on the type of data, compressing it into a ZIP file might make it small enough to send without running into trouble. But then the person on the other end has to know what a ZIP file is, and how to unzip it. (Check out WinZip for a good Windows-based ZIP program.)

A good alternative to sending the file by email would be to upload it to a website, and just send the web address of the file to the recipient.