Do family members have to pay (again)?

I added my wife as friend to access the server then as a household member. Now she can see the library on her phone but I get a pay wall message when playing something. First part is asking to upgrade to the Plex Pass, second mentions a $4.99 one-time purchase. How does that work for same household members, do I have to pay for each family member or do I need to use the same Plex Pass account on each family member app?

You need to add her to your Plex home:

https://support.plex.tv/articles/203815766-what-is-plex-home/

She won’t have to pay for the app and she will share the benefits of your Plex Pass.

Thanks, that’s what I was looking for. I had done that but there was no change on her phone for a while, it probably needs time to populate through the network. Now I see a “managed account” and the individual account I created as a “friend”, both work.

So if I wanted to give access to my brother outside my household, in that case he would need to buy the $5 to access my server, correct?

Yes, any user not in your Plex Home will have to pay the 1 time $5 fee to use the mobile app. If he doesn’t want to pay the $5, he can use the mobile browser.

No fee required for TV or PC app.

If your wife has an individual account, you do not need to create a managed account for her.

You can add her individual account to your Plex Home.
Manage Library Access → Click on her name → Click on the house icon to the right of Restrictions.
or
Plex Home → Invite Plex User/

From the document @happytaz linked:

Free Access to Plex apps (Plex Pass).

If the admin of the Plex Home has an active Plex Pass subscription, all members of a Plex Home (both Managed Users and regular accounts) will be able to use our regular mobile Plex apps from the various app stores without doing a separate one-time, in-app activation purchase.

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