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I am trying to re-format an external drive I have been using for a while just to clean it up. I hit "initialize hard drive" "yes" to delete any footage "yes" again to be sure you want to do that. Then it says the hard drive is in use and I have to switch to the internal drive first. I am on the internal drive. I can access its projects, so I know I am on that drive. Any suggestions?

You want the drive to be usable only on the Casablanca-3 an not usable at Casablanca-4 / Bogart Windows
Go to MediaManager -> Settings -> Device -> External Hard-Drive -> "Init extention hard-drive to format it. After that, use "Free extention hard-drive" so Bogart can use it after power off/on.

You want the drive to be usable at Casablanca-3 and Casablanca-4 / Bogart WIndows
Connect it to your PC -> In Windows XP, Vista, 7, 8 or 10 hold the "Windows" key and press "r" to type the command "diskmgmt.msc" and press enter. Find the external drive, delete the existing partitions, create a new partition and format it to NTFS.

On the Cassie, it still seems to do nothing. I hit initialize hard drive, it says you will lose the data, I hit yes, yes again after the next warning, and then nothing happens. Free extension hard drive remains grayed out.

Yes - yes - yes will not format the harddrive The risk of "user-error" would be to high.

Please read the text in those windows carefully and then hit the correct yes or no button

Got it. User error is my specialty.