Reinstalling the web server connector did nothing, but uninstalling the 4 
security patches that we had recently installed (NONE OF THEM having ANYTHING 
to do with IIS) got rid of the random/intermittent "HTTP 500" problem.

In case any of you start getting this problem, the 4 security patches were:

   KB950762
   KB950759
   KB951698
   KB950760

I dont know if it was all or one or some combo of the patches, but it was 
pretty bad. Again, it was only CF that had this problem. It recurred through 
multiple reboots and numerous "Revert to inherited" attempts as well as the 
reinstallation of the web server connector.

For comparison, the server is a CF8.01/IIS7/Windows Server 2008 x64 box on a 
dual Xeon quad-core processor.

I hope this doesnt happen to any of you.

>> Is there any way to force CF to use a different transfer 
>> encoding on all pages (without going into every page on every 
>> site on my server)? 
>
>I would try uninstalling and reinstalling the web server connector using the
>web server configuration utility.
>
>Dave Watts, CTO, Fig Leaf Software
>http://www.figleaf.com/
>
>Fig Leaf Software provides the highest caliber vendor-authorized
>instruction at our training centers in Washington DC, Atlanta,
>Chicago, Baltimore, Northern Virginia, or on-site at your location.
>Visit http://training.figleaf.com/ for more information! 

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