Comment by jeroenhd

The Debian installer is less than optimal for repartitioning.

The Linux NTFS resizing code also has a tendency to trigger data corruption. Not really Linux' fault, but it's a good reason to do partitioning from inside of Windows, which can be a pain already.

Another issue I've run into is Windows creating a very small (~300MiB) EFI partition that barely fits the Windows bootloader, let alone a Linux bootloader and kernel. You can resize and recreate the partition of course, but reconfiguring Windows to use a different boot partition is a special kind of hell I try to avoid.