Remote viewing not working with remote pass

Server Version#:4.159.0
Player Version#: ps5
<If providing server logs please do NOT turn on verbose logging, only debug logging should be enabled>

I have 1 users access my server from outside network for years. last week got the remote pass error and stoped working. I updated my account which is the account that runs the server to remote pass anual. he is still not working. does both his and my account have to have a remote pass to be able to get into my server?

The remote pass works for you, the user who has it (in this case: you) . It won’t give others the ability to stream remotely from your server (in this case: your friend).

https://support.plex.tv/articles/remote-watch-pass-overview/