1. This hasn’t been a notable issue in a while. That’s why Plex’s https-by-default was such a big deal. With https, even your ISP can’t see what you’re streaming. They can see that something is being streamed, but not what specifically.

Also, you totally glossed over the fact that Plex is simply easier for non-savvy people to set up. Plex provides a unified login experience similar to major streaming services, which Jellyfin simply can’t provide; If your mother-in-law can figure out how to log into Netflix on her TV, she can figure out how to log into Plex too.

And the unfortunate truth is that Plex’s remote access is much easier for 90% of users to figure out. It doesn’t require VPNs or reverse proxies at all. You just forward a port and anyone with access can easily see your server. But my MIL’s TV doesn’t even have access to a Jellyfin app without sideloading. Not to mention the fact that I’d need to walk her through actually setting the app up once it is installed, because there is no unified system for logging in. And if I’m not using a reverse proxy for my Jellyfin server, then I also need to walk her through setting up Tailscale, assuming her TV is even capable of using it at all.

Any single one of those hurdles would make Jellyfin a non-starter if I want to walk my MIL through the setup over the phone, and they’re all currently present. And some of them will never be fixed, by design. For instance, the lack of a unified login page is by design, because a unified login would require a centralized server for the app to phone home too. That centralization is exactly what Jellyfin was made to rebel against, so it’s a problem that will never be “solved”; It is seen by the devs and FOSS enthusiasts as a feature, not an issue.

From a FOSS perspective, Jellyfin is a modern marvel. But it’s definitely not at the same level as Plex when you compare ease of setup or remote access. Jellyfin is fine if you’re just using it locally, or are willing to run Tailscale to connect back to your home network. But if you’re looking for true seamless remote access and need to consider the mother-in-law factor, then Plex is hard to beat.

Calibre doesn’t natively support reading DRMed files, but there are anti-DRM plugins which are trivial to install. You need to provide a legitimate Kindle serial number for Amazon DRM, as it uses that to de-encrypt the files. When you add the file(s) to your library, the plugin automatically runs as a file conversion. It basically converts it from a DRM-locked .epub/.azw3 to a DRM-free .epub/.azw3 instead. Since Calibre already has file conversions built in, the plugin simply uses that existing system to spit out a DRM-free version of the same file, then it adds that to your library instead.

Because running it on your router gives you access to the entire network of devices, not just the Jellyfin server.

Not in the way you’re probably thinking, no. The VPN (like Proton) will be isolating devices from each other. This is by design, so you don’t end up in situations like different customers seeing each other on the network.

Your router might be able to act as a VPN host. This would allow you to connect to your home network from anywhere, and use it just like you would use a service like Proton. And if your home network is set to allow devices to see each other, then you could see your Jellyfin server. See if your router can run Tailscale or can act as a WireGuard (or OpenVPN) host. Tailscale will be the most straightforward approach, but not everything can run it. Worst case scenario, you could just run Tailscale directly on your Jellyfin server.

The big issue with requiring a VPN is that it makes remote access on some devices difficult or damned near impossible. For instance, good luck getting a smart TV to run Tailscale. Tailscale will be fine for things like phones, laptops, or tablets. But if you have a smart TV you want to remote view things on, you may need to consider a reverse proxy instead. And a reverse proxy is such a rabbit hole that it would deserve its own post.

Yeah, this is the unfortunate truth. Jellyfin’s setup will never be as simple as Plex, purely because the simple setup requires a centralized server to coordinate things. And Jellyfin is built specifically to rebel against centralization. Plex is easy because the company has servers set up specifically to handle the remote access handshake.

Because of the Wife Factor. Getting people to convert requires getting past a lot of social inertia. It requires you to first convince them that the convenience of streaming services isn’t actually worth paying for. Then it requires an elegant onboarding experience. Lastly, Plex simply makes remote access easy. Sure, you could fiddle with reverse proxies for Jellyfin. But that’s easy to mess up. Instead, it’s much smoother to simply sign into Plex.

I can talk my tech-illiterate “My google chrome desktop icon got moved, and now I don’t know how to check my email” mother-in-law through Plex’s sign-up process over the phone. In fact, I did. It’s familiar enough that anyone who has signed up for a streaming service can figure it out. I can’t do that with Jellyfin, because their eyes glaze over as soon as you start talking about custom server URLs or IP addresses. Hell, my MIL’s TV doesn’t even have a native Jellyfin app available on the App Store. If I wanted to install it for her, I would need to sideload it.

Jellyfin does a lot of things right. But by design, the setup process will never be as elegant as Plex’s, because that elegant system requires a centralized server to actually handle it. And centralized servers are exactly what Jellyfin was built to rebel against.

To be clear, I run both concurrently; Jellyfin for myself, and Plex for friends/family. I got the lifetime Plex Pass license a decade ago, and it has more than paid for itself since then. But it sounds like a bunch of my friends and family may end up switching to Jellyfin if they don’t want to deal with the PlexPass subscription.