I have experienced some major headaches recently with confusing behaviours and would like to share my findings...

HTTPS alone does not determine if a resource will be cached. Different browsers and versions have different default behaviours.

"Do not save encrypted pages to disk". By default, this user setting is unchecked on Windows clients and checked on Windows Server. Using this option may cause "Internet Explorer cannot download" dialog.

Previously cached resources may be ignored, causing increased network requests.  Odd but true.

Back/Forward optimization does not check the freshness of cache resources. 
In other words, users will see what they saw. This is specific to IE9 following RFC2616 and requires a refresh or F5 to view page modifications during development. This is different than previous versions of IE.

Detailed explanations worth reading can be found here:

http://blogs.msdn.com/b/ieinternals/a...

http://blogs.msdn.com/b/ie/archive/20...

I hope these tidbits will save you some time and effort.

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Dwayne J. Baldwin

Nice addition, thanks!

It's hard to reproduce nevermind debug multiple moving targets. What I would really like is a keyboard shortcut called "Fix It And Forget It".

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Dwayne J. Baldwin