On my Roku’s, I think I have had to sign in only once for each device. The kids have been using Plex Web for several months now on their PCs and I only have signed in once there too.
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Mine’s been working for years on Androids, Rokus and computers. I think the only time I have to sign is when I get a new device.
If you have your web browser set to clear cookies and such when closing, you may have to sign in each time. Not sure how that works. 
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Thank you both
unless you explicitly sign out, the client should normally stay signed in.
and there is an option to ‘automatically sign in’ (with the last selected user), otherwise the user profile picker should pop up upon client load.
that said, any client/device that does need signed in, yes will need YOUR plex email/password. (which is a primary reason to have your users/family create their own plex accounts, so they can sign in their own user/pass)
if for some reason an existing device gets reset or otherwise signed out, a managed user will require YOUR plex email/pass (that means you sign in, or you share your password, not recommended).
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