Moving to Plex

If you follow me on Twitter, you may have been wondering why I installed Snow Leopard — an operating system that’s over five years old — on my iMac over the weekend. It wasn’t for nostalgia or even to breathe new life into an aging machine, it’s all part of my plan to move my Mac mini’s media hosting setup from iTunes to Plex. As it turns out, there are some interesting tricks you can do with iTunes media on the unsupported OS.

It started last Thursday, when I decided to revisit Plex. The app seems to be the standard for cool guy media hosting these days, but in my previous testing I didn’t like it. I had a terrible time navigating the application’s preferences and couldn’t understand how to find the features I was looking for. Now I’m not sure if there have been major updates to the app since then, but for whatever reason, Plex has clicked for me — big time.

I’ve already laid the groundwork to going all-in on Plex. I have the server app installed on my Mac mini, with all of my media files indexed, and I’ve installed the client apps on my Apple TV, iPhone, and iPad. I’ve tried out several of the app’s plugins and have settled into using the HGTV and Food Network channels to fill a gap in our cable-less entertainment offerings. I’ve even integrated Watch Later into my life with a Workflow that uses the feature’s secret email address to add videos to my queue.

There’s just two more hurdles to overcome before I can close iTunes on my Mac mini for good. The first requires a hardware upgrade and the second will just take time.

We have two televisions in our apartment, one in the living and one in the bedroom. Each of them has an Apple TV connected, but the bedroom has the previous-generation, which doesn’t support Plex. My strategy has always been to upgrade the living room Apple TV when a new model is released and retire the old one into the bedroom. That way we’d always have the latest and greatest on our primary TV and the previous-generation in the bedroom.

With my newfound interest in Plex, though, this upgrade cycle might have to be disrupted. I would prefer to have the same television experience in the living room as I do in the bedroom — using the exact same apps and remote. I’ve been able to justify waiting for Apple to release their next Apple TV because there wasn’t anything we had access to in the living room that we couldn’t get in the bedroom. But because of Plex, that’s no longer the case.

I don’t really want to spend $149 on an Apple TV that’s over a year old, but Plex is a huge draw. And finally retiring our old Logitech Harmony is nothing to scoff at. I expect I’ll end up biting the bullet and buying another Apple TV, but I’ll probably wait until closer to the holidays when I might find one at a discount.

I’ve already invested a great deal of time toward the second hurdle and it’s the reason I installed Snow Leopard on my iMac. I’ve been so happy with Plex that I’ve gone through the trouble of installing a five-year-old operating system just so I can use Requiem. This brilliant piece of software hasn’t been updated since 2012, but on older versions of iTunes — I’m using 10.6.3 — it’s capable of making perfect, DRM-free versions of your purchased movies and TV shows by exploiting a flaw in the copy protection mechanism.

The process involves downloading my purchased media through iTunes, quitting the app, launching Requiem, waiting for it to churn through the files, and moving them to my Plex folder on my Mac mini. I’ve been doing this dance since Saturday night and I’ve successfully transferred sixty-six movies and four television seasons. At the time of this writing, I still have seventeen TV seasons to go, but I can definitely see the light at the end of the tunnel.

I do think it’s important to note that I’m not using Requiem for piracy purposes and wouldn’t condone anyone else doing so. I just want to exercise my right to fair use by watching the content I’ve paid for on the player of my choosing. And having all of my iTunes purchased content and ripped DVDs in one place is definitely worth the effort.

Now I can use Requiem to strip the DRM from my iTunes purchases in the same way I’d use Handbrake to rip DVDs. As long as Apple doesn’t shut off access to the iTunes Music Store on these older versions of iTunes, I’ll be able to use these tools to merge my physical and digital media into a single, unified library and host it all with Plex.

The biggest benefit to all of this is that my media is now completely disassociated from any specific platform or vendor. It can be viewed wherever, whenever, and however I want. I’m using Plex currently, but without my files being laden with copy protection, I can freely move to any other player or platform and not have to worry about incompatibilities. It may have taken me a dozen hours to convert the media from their original format, but this kind of freedom is definitely worth the effort.