I have renamed the default Settings > Media Types > Image to "Image SiteA" and the (default) "Folder" to "Folder SiteA" then created a new folder "SiteA" and moved the newly renamed "Image SiteA" and "Folder SiteA" into it. I then have created a new folder called "SiteB" and created a media type "Folder SiteB" and "Image SiteB" both with the exact same settings as SiteA except the Image cropper is different SiteA / SiteB. I have set the Permissions of both so "Folder SiteA" can only have "Folder SiteA" and "Image SiteA" (and same for site B).

In Media > This is all working fine when you right click into a SiteA folder you can only add an "Image SiteA" and in a folder SiteB you can only add an "Image SiteB". However, If when you are in a "Folder SiteB" and you Drag files into the upload area they are added as type "Image SiteA".

Any ideas on how to resolve?