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I know that there are some similar topics to this, however I was not sure which of them could be applied to my case. Because I am afraid of destroying my system, I hope you can give me some advice on how to proceed:

On my laptop, I have installed Ubuntu 16.04 and Windows 10 as a dualboot system managed by GRUB. You can see my partitioning in this:

GParted screenshot

Now I want to increase the size of my Windows partition (/dev/sda3) and decrease the size of my Ubuntu partition (/dev/sda2). If I just move the border in GParted (after booting from an Ubuntu USB stick), will both of my systems work as before? What about GRUB?

How would you proceed in my case to do this partition resizing?

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Look, resizing and changing partitions can be a complex and a confusing process and it might cause you to loose some data from any of your stated OS's or lock you away from your system(or even worse, you might end up having unused space without any access). I had tried your case quite a time earlier with Gparted and ended up losing my windows data. So please try backing up all your data and reinstalling the os with your required size.

Thanks,

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The short answer to your question is, yes resizing your Ubuntu partition from your live medium should not cause any issues with stability.

IMPORTANT: If you're concerned about losing data. Back up the files you care about before proceeding. Any shrinkage or movement of partitions has the potential to cause data loss (though it is typically rare and has never occured in my experience). If you possess an external hard drive or a USB that's large enough to contain a clone of your current partitioning scheme, I'd highly recommend creating a bootable CD/USB of Clonezilla, which can create an exact copy of your hard drive in your machine and restore it if something goes awry. It's saved me numerous times.

Resizing your partitions

To resize your Ubuntu partition, you will need to boot from the live CD/USB and use GParted from there. Once inside GParted on the live CD/USB, select the Ubuntu partition and shrink it to your liking.

Warning: Do NOT use GParted to resize/move the Windows NTFS partition. While GParted is capable of doing so, this can cause issues on Window's end. Back when I dual booted Windows 10 and Ubuntu, I used GParted to resize the partition Windows resided on, and it prompted Windows to insist that the filesystem needed to be checked for errors. Luckily, after running check disk, everything was fine; however, data loss is entirely possible. Once, you've changed your Ubuntu partition, reboot into Ubuntu to ensure that your files are intact and nothing is damaged.

Note: I haven't been in your exact situation, but I would imagine that unallocated space will be separating your Ubuntu partition and your Windows partition after shrinking the one Ubuntu resides in. This will be an issue if Windows cannot manipulate that unallocated data on its own (as it is behind the Windows paritiition). Try what I've described below.

Next, boot into your Windows partition and open up the Disk Management Tool. From there, you can add unallocated space to your Windows partition and extend it. If for some reason Windows cannot manipulate the unallocated space after the Ubuntu partition, then you have a couple options:

  • Download a third-party tool such as MiniTool Partition Wizard, EaseUs Partition Manager, and others. Personally, I have not used nor can I vouch for either of these tools. LifeWire actually has an article called 10 Free Disk Partition Software Tools that was published recently (3/06/2018) where you can find a few more utilities with brief descriptions.
  • Use GParted. GParted was actually mentioned in the LifeWire article I linked to. Despite my previous warning to not use GParted to resize/move your Windows partition, I trust GParted more than some of the other utilities out there.
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