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Why does "Enable offline files" uncheck itself after a reboot?

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After my two previous posts on debugging offline files, I’ve had four requests via comments and email, all saying pretty much the same thing: “why do offline files stop working after I restart my computer?” The most visible symptom is that the “Enable offline files” checkbox gets cleared after a reboot. I passed this request along to the team responsible for offline files, aka client-side caching, and here’s an explanation from Brian Aust.

These are the checks that are made on CSC startup:

  1. CSC is not enabled on Home Edition
  2. CSC is not enabled when terminal server is configured for multiple concurrent users
  3. CSC is not enabled when either the user’s (admin user) preference or Group Policy says it should be disabled
  4. CSC is not enabled when either of the following REG_DWORD registry values is set to zero:
    HKLM\Software\Microsoft\Windows\ CurrentVersion\NetCache\Enabled
    HKLM\Software\Policies\Microsoft\ Windows\NetCache\Enabled

ONLY if all those conditions are met will the checkbox stay enabled over a reboot — so if you’re suffering from this problem, those are the four things to check!

Update: for additional things to check, see the comments below, and this later blog post.

Edit: I've turned off comments on this thread - if you have a question, please go here instead.