Would it be fair to say you should not use shadow in an attempt to meet adequate contrast even if the rendered layered up colour does - purely because this would be knocked out in high contrast mode, making high contrast mode have lower contrast?
Example: Text shadow over image
@iknowdavehouse sounds right, isn't there a workaround with transparent outline? I think I heard that works
@joelanman on objects for sure - focus states etc with box shadow. I’m thinking something that actually looks like a shadow so rendering as an outline might weird (especially on text)