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Are you using Asp Classic or Asp.Net? I see this happen more often in Asp Classic then Asp.net, but it possible in both.
How do I test where the programming error originated?
Wouldn't that be nirvana? ;)
Actually, we've done that. We have a 500 Error reporting utility (our own) that records every single 500 and sends emails when they occur. The emails are usually a "complete dump" of all information required to track and correct the error. Some of them are rather difficult to backtrack but we do get to all of them.
500s = Kiss of Death
Too many Classic ASP sites running out there not knowing if their apps are generating 500 errors. Most visitors will not alert you to the issues and some may be totally invisible, seamless. But, the function on the backend failed. And who knows, it may have just caused 100% CPU use and used 1 GIG of RAM. Ask me, I know. As early as this morning. Darn typos! :)
P.S. Adding a 400/500 Error reporting utility is the best thing a Windows Website Administrator can do. You'd be surprised at the number of 500 Errors that you'll see initially. Oh sure, everything seems to be running smoothly. But, deep down inside, there are ghosts in the machine.