Setup Let's Encrypt certificate for use with Plex Media Server on Ubuntu

LetsEncrypt_HTTPS_plex.MD

Prep

Your ceritifcate files should now be in this directory: /etc/letsencrypt/live/myhostname.no-ip.org/

I also assume your Plex server is port-forwarded to be accessible via port 32400: http://myhostname.no-ip.org:32400

Set up the certificate

Before we begin, we need to generate a PKCS #12 (.pfx) file from the Let's Encrypt certificate files. It's all the Let's Encrypt files archived, and bundled into one file.

Create the PCKS #12 file:

1. Run the package command:

     sudo openssl pkcs12 -export -out /var/lib/plexmediaserver/certificate.pfx \
       -inkey /etc/letsencrypt/live/myhostname.no-ip.org/privkey.pem \
       -in /etc/letsencrypt/live/myhostname.no-ip.org/cert.pem \
       -certfile /etc/letsencrypt/live/myhostname.no-ip.org/chain.pem \
       -passout pass:

2. Hand it over to plex.

   sudo chown plex:plex /var/lib/plexmediaserver/certificate.pfx

Have Plex use your PFX file

1. Visit the Plex UI on your server: http://myhostname.no-ip.org:32400

2. Go to Settings (icon on top right corner) > Server (tab) > Network (left navigation column).

   Click "SHOW ADVANCED" to see the necessary fields.

3. Enter the following values:

   • Custom certificate location: /var/lib/plexmediaserver/certificate.pfx
   • Custom certificate encryption key: The password you entered on step 2 of last section
   • Custom certificate domain: https://myhostname.no-ip.org:32400

4. Save your changes.

That's it. You don't even have to restart plex!

You can check the Plex\ Media\ Server.log file in /var/lib/plexmediaserver/Library/Application\ Support/Plex\ Media\ Server/Logs if you want to verify whether there were any errors.

Visit your server at https://myhostname.no-ip.org:32400 (Custom certificate domain) and see the HTTPS in action.