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Helpful answers
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Aug 28, 2015 6:44 AM in response to Guy Emersonby JimmyCMPIT,you appear to have more than enough space to do this, but if your putting files in the trash and erasing them you are reclaiming that space.
the question is why are you doing this. Unless you need to securely delete files so there is no chance to recover them I suggest you read this
https://support.apple.com/en-us/HT201949
if this is what you need to do and it's not working I would disconnect all external devices, then boot into safe mode, then try to erase free space.
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Aug 28, 2015 7:01 AM in response to JimmyCMPITby Guy Emerson,Thanks. I was just trying to free up as much space as possible - hence moving my Photos to an external drive and according to other discussions this is supposed to help. However as it never completes ( I only use the fastest option) and does not create any more free space, I guess it does not matter.
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Aug 28, 2015 7:15 AM in response to Guy Emersonby JimmyCMPIT,if you don't empty the trash it wont reclaim any space when you "trash" the file until you empty it out, it's essentially a folder. You probably know that but not everyone does so I thought I'd ask.
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Aug 28, 2015 12:55 PM in response to Guy Emersonby Eric Root,Do a backup, preferable 2 separate ones on 2 drives. Boot to the Recovery Volume (command - R on a restart or hold down the option/alt key during a restart and select Recovery Volume). See if you can do the erase there.