I can't say I've ever experienced that problem on either my 718 or on my previous Porsche's, though I once experienced a similar problem on the drivers door of an Audi I once owned.
If you haven't done so already you could try re-setting the window mechanisms. Page 305 | 2017-2019 718 Boxster Manual | Porsche iManuals It'll be the same procedure for both Boxster & Cayman.
Failing that try a suitable rubber seal lubricant, it's possible that the windows might just be binding a little tightly against the rubber. (Referring back to the Audi it was rubber lubricant that did the trick).