I have a Windows Server 2003 system running PHP 5.2.10, MySQL 5.0.83, and WordPress 2.8.0.
The blog itself works perfectly, and I can upload images perfectly from the web admin interface.
When I post a text-only entry from Windows Live writer it also works perfectly. If I attempt to upload images, I get the following error:
The server reported an error with the following URL:
http://www.thelakeclubohio.com/wordpress/xmlrpc.php
500 Server Error
What's interesting is that I can see the first image in the post upload fine. The file is there, inherits the appropriate permissions, and can be opened.
I can send the log file if I need to, but I'm hoping this is something simple that I can check for. Any ideas?