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I have a supervised iPad that was used to make training videos, the issue is that they have nigh completely filled the device of videos. I am unable to use iTunes to manage it as the device is locked to a single computer which happens to be in a different country, as such sending it back there just to have it sorted is a last case scenario.

The issue is that no matter what type of backup I try and perform, the system is reserving 6GB for itself and the videos taking up the remaining 10GB of the 16GB device, which basically fails every single backup attempt due to insufficient space (Just to confirm I got 50GB limit on iCloud, with 0GB in use). Is there no way to tell the system to re-evaluate what it's keeping reserved because I am pretty sure it's just a bunch of old backup references or temporary files. Also how much space is required on the device to perform this backup?

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So I left the iPad overnight and it successfully uploaded everything to iCloud despite having very little available space. I believe this may have something to do with the fact that I manually started a backup via Settings->Name->iCloud->iCloud Backup->Back Up Now rather than using iCloud Photo Library/Sharing function. The backup did complain about not having sufficient space but at some stage it seems to have kicked in, perhaps the device re-evaluated what it was reserving in system storage and made sufficient space.

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One way to see what is taking up space on a device is through the Settings app >> General >> iPad Storage. Here, you can see a breakdown of what app/service is using how much space. This will also show you how much space the system is holding or taking up. You can also Offload apps to save space.

Hope this helps!

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    The iPad in question was a supervised work iPad which did not allow any apps installed apart from default/work related apps, as such there was not much to get rid off. - Thankfully the problem somewhat sorted itself out as I'll explain in my own answer. – Senko May 1 '19 at 9:31

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