This is an ASP.NET 1.1 issue. We have a HttpHandler that does a
Server.Execute to an ASPX page which has output caching enabled.

The directive in the ASPX page is:

<%@ OutputCache VaryByParam="*" VaryByCustom="guestPage" Duration="60"
Location="Server" %>

This works fine in our development and staging environment. When we deploy
new binaries to our production server it doesn’t work (however after a
certain it starts working as expected!!!). The development and staging
environments are in GMT+10 hrs. The production environment is GMT-6 hrs. It
appears that there’s some sort of caching/conflict occurring. The caching
starts to work when the clock on the production server is brought forward 8
hours. Changing the timezone/clock on the machine doing the build to match
the production clock doesn’t help – you still need to wait 8 hrs. We’ve tried
deleting the Temporary ASP.NET files and a full server reboot – it doesn’t
appear to help.

The caching works as soon as the changes are deployed for a HTTP request
sent directly to the Web Form. Also, the form has additional fragment caching
which also works immediately.
Any help in regards to this would be appreciated.