I’ve given my friend access to my Plex library, as well as allowed downloads. They’re able to stream from the Plex web player, but don’t have the option to download. I have Plex pass, so I think they should be able to. Am I missing something?
Your friend must have a Plex Pass or be part of your Plex Home.
Plex Docs → Downloads for Offline Use → Downloads Overview
Tip! : The Downloads feature requires an active Plex Pass subscription on the user account performing the Downloads action. Managed Users in a Plex Home of a user with a Plex Pass will also be able to use Downloads.
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