A tweet by @jonasLyk reminded me of a bug I found in NTFS a few months back, which I've verified still exists in Windows 10 2004. As far as I can tell it's not directly usable to circumvent security but it feels like a bug which could be used in a chain. NTFS is a good demonstration of how complex writing a FS driver is on Windows, so it's hardly surprising that so many weird edges cases pop up over time.
