Hello @kimberlyp673 ,
The buttons on the side are meant for the single file they share a row with. When selecting multiple Library files to either add to a folder or delete, I'd advise using the options at the top:
For the pop-up window for individual files, you have to make sure to click the Save button after selecting the other file, otherwise it won't maintain that selection change:
For further guidance regarding Library management, I'd advise checking out these articles (also available via the Help tab in your account):
Create and manage Library folders
Use the Advanced Search tool in your Library
Remove or permanently delete an image or document from the Library
... View more