Updating Plex on Synology NAS

My family has been using ChromeCast to send YouTube videos to the TV. While flipping through the ChromeCast app on my phone, I noticed Plex integrates with ChromeCast. Funny enough, Synology also ships a Plex server package. How hard could this be?

ChromeCast: Easy Come, Easy Stow

I have a very curious toddler.

The ChromeCast is easy to hook up and break down as needed when you want to use it, and there’s not much to break. It was a simple and immediate solution to make the TV usable again without needing to run any cables or install a shelf outside toddler reach.

Before this, we spent several months with the TV completely unplugged after we dismantled the entertainment center and mounted the TV to the wall as part of making our living room child-resistant.

(Child-proof vs child-resistant is like waterproof/water-resistant: Nature finds a way, and all we can do is try to hold out – in this case, till an adult notices a curious and ill-omened silence.)

Plex Client Is Picky; Synology Plex Is Old

Setting up the app on my phone was fairly easy. I needed to create a new login, which, yawn, but 1Password is with me.

Installing the package on my NAS was also one-click.

Getting them talking to each other was a bloody mess. Plex client is very aggressive about not working with older versions of Plex server, which meant that right now, it didn’t work at all with the version packaged by Synology.

Installing a Manual Package

Luckily, Plex packages Plex Server for Synology (and several other flavors of NAS) themselves.

Their instructions only cover a small part of the install process, though. What papered over the gap for me is this article. (That article has pictures, unlike this one.)

Here are the steps I followed:

• Check your processor type in the Synology Control Panel
• Download the package for that processor type from Plex Downloads
• Download the Plex package signing key linked from here
• Verify the md5sum they give you for what comfort that might give. (md5sum? Really?)
• Open the Synology package center and hit the Settings button:
  • On the General pane, widen your trust from just Synology to Synology plus trusted publishers.
  • On the Certificate pane, upload the PlexSign.key you just grabbed.
    • Now Plex is a trusted publisher.
• Exit the Settings modal and hit the Manual Install button.
  • Select the Plex package you downloaded.
  • Wait for it to upload, then OK the install.

Unfortunately, Plex doesn’t seem to publish a stream of updates, just individual packages, so when the client yells at you again about the server being too old, you get to repeat most of this dance.

Gotchas

Potential: Synology vs Plex package differences

I read some tales of issues with swiching between the two packages. I know that installing the Synology version first and then the Plex version worked fine for me. Your mileage may vary. If it breaks, you might need to pop the hood and ssh in to see what’s gone wrong.

I didn’t encounter any issues myself, so I wouldn’t worry about this unless you run into it.

Derp: Manual packages must be uploaded from the client

If you’re like me, you might think like this:

• I will need to install this package to the NAS.
• The package file needs to end up on the NAS eventually.
• Downloading the package file directly to the NAS using Download Station will save transfer time.

You’re right in theory, and wrong in practice, because the manual install flow only lets you select a local file to upload. Let me say this again: There is no way to point the manual install wizard at a package that’s already downloaded to the NAS. You have to upload it from your local machine directly to the manual package installer.

The fun end result of this is that, if you downloaded the file to the NAS to begin with, you now get to download the file from your NAS so you can upload it back for the manual package install flow.

The steps I listed above skip this time-wasting cleverness.

Conclusion

Plex would be a lot easier to use if they’d do a better job of preserving client–server compatibility across versions.

If you’ve been looking for an excuse to wander into manual Synology package installation, though, you’ve come to the right product.