Download File feature not available between to Plex Pass Lifetime accounts

Server Version#: 1.32.4.7195-7c8f9d3b6
Player Version#: 4.108.0
A friend of mine and I have been using Plex for years and we both have Plex Pass Lifetime subscriptions. A reason we both purchased those subscriptions was for the ability to download an occasional file from each other’s libraries. We ended up not really using that feature, but it was nice to know it was there.
The other day I went to download a file from one of his libraries and noticed the Download File option did not display in the popup menu.
We got on the phone yesterday evening to discuss it and we verified that we both have the option checked for each other that allows us to download files from each other. However, neither of us sees the Download File menu item when pulling up the popup menu for any content in each other’s libraries.
We do see the Download File option in each of our own respective libraries, just not for content in each other’s libraries.
I use Plex Server for PC and he uses Plex Server for Mac. We know we used to see the Download File option in the past, and we’re not sure what has changed.
Any help in this matter would be greatly appreciated.

The Download feature is available in the mobile clients (Plex for iOS/Android) and the regular desktop apps (Plex for Mac/Windows/Linux).

Based on your description I guess you’re referring to the Safe File option that’s available in Plex Web for the admin of a server.

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