Oh so what you are saying is is that your second server is not on the same network, let alone the same hosting environment. In that case allowing IWAM_[machineName] will not work because Server 2 will have no idea about server 1's IWAM account.
What you will probably need to do is, a user uploads an image to server 1, after the file is uploaded call an FTP process that will automatically take that file and place it in the directory on server 2.
(Note: .NET 1.1 does not natively support FTP, however, there is an article on the MSDN that explains how to set up an FTP Class to facilitate this kind of transport. All that will have to be done on Server 2 is to make sure an ftp server is setup and running and that your FTP class is calling a user that has rights to access the FTP server.)
hth
"The one language all programmers understand is profanity."
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