Hey Michael,
Windows update's cause me all kinds of trouble. I have no idea if it will help with this situation or not, but after Windows updates I often need to uninstall & reinstall 'Microsoft C++ Distributables' to get my programs functioning again. If Clothworks uses C++ it could be affected...?
(After last months update, I lost one of my NVMe drives from showing up in BIOS...and I still havent' got it working again.... (thanks MS))