I have a production server running Microsoft IIS 7 (Version 7.0.6000.16386) on Windows Server Web (2008) Service Pack 2. During the month (or perhaps 2 months), some of our older web pages using ASP Classic have been throwing 500 Server Errors. In the IIS log it shows "ASP_0147|500_Server_Error" and "ASP_0113|Script_timed_out" errors. I've narrowed it down to certain ASP pages that are creating server XMLHTTP objects [Server.CreateObject("Microsoft.XMLHTTP") ] in order to "POST" data to an on-line credit card merchant processor. About 90% of the time these pages work just fine. The other 10% of the time, they are throwing one of these two errors. These pages have been in production for many years and have worked flawlessly until recently. Nothing on the server has been reconfigured. The only update has been the usual Windows Updates from Microsoft, which have been dutifully applied when they come out. I'm at a loss as to what is causing these issues. I'm toying the idea of rewriting these pages using ASP.NET, but that will some take time. Is there anything I can do or check on the server to figure out what is going on? Side note: The server is actually running as a Virtual Machine on VMware. I've added more memory and a second processor to the virtual machine thinking it was simply a low resource issue. But, that did not help.