I was able to replicate this, exactly as you said. That is a Bug. Report it to Roll20 Help Center if you have time time. That's the way to bring it to the attention of the developers. <a href="https://help.roll20.net/hc/en-us/requests/new" rel="nofollow">https://help.roll20.net/hc/en-us/requests/new</a> In the meantime I would suggest, try to make your rectangle the shape/length that you want before rotating it.