I tried to delete the old image files in the File Manager, but it seems no options for me to be able to select files by date…
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Normally you wouldn’t directly access the File Manager to do this cleanup, but instead keep the images tied to things’ file/image fields in your database so you can sort those things by date and delete their files.
Sorting by Upload date does work but it seems like it only sorts what is on the page, and it sets the number of items when you sort… 
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