After trying many things with permissions, I found my problem.
I uses a plugin called Duplicator to move WordPress installs around from server to server, it handles changing URLS’s and Paths.
So in settings => Media => Store uploads in this folder
it was setting the Full Filepath to my Uploads folder. I changed it to be relative wp-content/uploads
instead of full like this E:/Server/htdocs/projects/sitename/www/wp-content/uploads
and the problem went away!
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