If I have purchased a movie and have it ripped unto my Plex server what are the legalities of streaming that to friends and family.
At the moment I probably have 3 or 4 people using the server.
I know Plex only licenses the software and what I do with it is my business but I’m just looking for some direction on this.
That’s a difficult question, because it varies from country to country and maybe even state to state. You’d be better off consulting legal experts in your country or locality.
Here’s some general info: https://en.wikipedia.org/wiki/Legal_aspects_of_file_sharing#United_States
Ripping itself is illegal since you are breaching the copy protection.
For the rest I would consult a lawyer 
I know what I think doesn’t affect the law, but I equate it with letting a friend borrow a DVD.
Which is not the same thing obviously:
@Coxeroni said:
Ripping itself is illegal since you are breaching the copy protection.
For the rest I would consult a lawyer
That is, mostly, only true in the US and a very few other countries. Many/most countries have governments that have not been bought by the media. The governments of other countries may be corrupt in other ways but many actually protect the consumer over the big media corporations.
I doubt, in most countries, that simple sharing by allowing a few people to watch movies via your server would be prosecuted or even detected. Of course if you charge or share with a lot of people or provide downloads you increase your risk quite a bit.
The other part is that Plex’s data streams are pretty much encrypted so it would take some effort to detect what is being streamed.
But I do not and will not share. But it has nothing to do with legalities the only people I like enough to share my media with are my daughter and granddaughters and they are currently living in Europe (Switzerland most of the time) and they are too busy living their life to watch much media and my upload is quite slow.
@Elijah_Baley said:
@Coxeroni said:
Ripping itself is illegal since you are breaching the copy protection.
For the rest I would consult a lawyerI doubt, in most countries, that simple sharing by allowing a few people to watch movies via your server would be prosecuted or even detected. Of course if you charge or share with a lot of people or provide downloads you increase your risk quite a bit.
Whether it will prosecuted or not is a different story and I agree with you there, but this has nothing to do that it is illegal, in my opinion in most countries, a) to make a digital copy and b) to share it with someone else. Chances are high that either one or both are illegal in your country, which is what was asked for.
Edit: I was wrong about the ripping:
Seems as nowadays a lot of countries allow a private copy. But if you share it with someone else, I would say this right way stretched too far.
