I have a Mac the I sent the encryption command to through Casper but it is failing to start/complete encryption.
Casper shows FileVault 2 Partition Encryption State:Restart Needed
The Mac shows Filevault is turned off
Every time they log in they are prompted to enable Filevault. Once you click enable it does not restart, it just logs straight in.
Has the Mac in question actually been restarted since making these attempts? Or is the user just logging out and logging back in? Its a bit unclear from your description. I ask because, CoreStorage (for FileVault 2) is a bit finicky in how it works. If the Mac was ever previously encrypted and then decrypted, for example, the Mac must be restarted fully to remove the remnants of the previous CoreStorage volume, even if it shows as not being encrypted. Until thats done, creating a new CoreStorage volume for FileVault will fail.
If it has been restarted and its not enabling, then its likely something else is going on. Does it have a working Recovery HD partition?
Also, is it on the latest OS release? Run all software updates and try the process again. Some of the earlier versions of El Cap had this issue that were fixed in subsequent releases.
Does the Mac have all the requirements for FileVault such as a Recovery Volume and core storage enabled etc
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