What wifi chip are you using? Debian by default has no unfree wifi drivers included, so that can cause issues with them. If you have a good wifi adapter by a vendor that pushes drivers upstream like Mediatek, it should work just fine out of the box.
Yes I was using the non-free version. It was working fine until I'd set the machines to auto-update then one day found out they had zero connectivity after an update. I thought about going around to each machine and manually trying to revert back whatever was in the updates that broke it and just decided to wipe and install Ubuntu back on them.
