How to check/set permissions so Plex can delete media?

Server Version#: 1.21.2.3943
Player Version#:

Hello I have had a heck of a time setting this up, I finally got remote access working and plex to see my external HDD connected to the pi. But I want to delete old media easily. I made sure the setting to delete media is allowed but when I try I get the error " There was a problem deleting this item." Where in the logs can I see what is happening or what can I do to resolve this? This is on a raspberry pi 4. Thank you for the help!

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