File uploads

1. I noticed that when drag and dropping files, if I click “add files” the file is added to the correct category. However, if I just drag and drop, the file is still added but has no category. This is confusing behavior. Is there a way to make sure the file always goes into the correct category.
2. I am wondering if it is possible to explicitly set permissions based on user role. I realize that this can be done by the UI but I want it done prior to uploading. Is there some kind of filter or action support for this?

I am currently using the free version but will upgrade if these items are supported.

thanks.

http://ww.wp.xz.cn/extend/plugins/wp-filebase/