My server settings page says "An update is available. Please install manually." That's normal. I've never had a problem with this before.
Clicking the link downloads the 99.1MB .deb installer correctly, to the best of my knowledge.
Double-clicking the downloaded file (plexmediaserver_1.3.0.3059-6277334_amd64.deb) launches the software installer window. Just like normal.
Clicking the "Install" button begins the process, and an orange progress bar appears under the button, but it fails to complete the installation.
Instead, it stops, and the screen display reverts to showing Version 1.2.7.2987-1bef33a.
On Twitter, @plex suggested I post here, and that I include the installation logs. This is what's added to syslog when I try to run the installer.
Nov 27 16:51:20 ubuntu dbus[755]: [system] Activating via systemd: service name='org.freedesktop.hostname1' unit='dbus-org.freedesktop.hostname1.service'
Nov 27 16:51:20 ubuntu systemd[1]: Starting Hostname Service...
Nov 27 16:51:20 ubuntu dbus[755]: [system] Successfully activated service 'org.freedesktop.hostname1'
Nov 27 16:51:20 ubuntu systemd[1]: Started Hostname Service.
Nov 27 16:51:24 ubuntu dbus[755]: [system] Activating service name='org.debian.apt' (using servicehelper)
Nov 27 16:51:24 ubuntu AptDaemon: INFO: Initializing daemon
Nov 27 16:51:24 ubuntu org.debian.apt[755]: 16:51:24 AptDaemon [INFO]: Initializing daemon
Nov 27 16:51:24 ubuntu dbus[755]: [system] Successfully activated service 'org.debian.apt'
Nov 27 16:51:24 ubuntu AptDaemon.PackageKit: INFO: Initializing PackageKit compat layer
Nov 27 16:51:24 ubuntu org.debian.apt[755]: /usr/lib/python3/dist-packages/aptdaemon/worker/pkworker.py:35: PyGIWarning: PackageKitGlib was imported without specifying a version first. Use gi.require_version('PackageKitGlib', '1.0') before import to ensure that the right version gets loaded.
Nov 27 16:51:24 ubuntu org.debian.apt[755]: from gi.repository import PackageKitGlib as pk
Nov 27 16:51:24 ubuntu org.debian.apt[755]: 16:51:24 AptDaemon.PackageKit [INFO]: Initializing PackageKit compat layer
Nov 27 16:51:24 ubuntu AptDaemon: INFO: InstallFile() was called: /home/jmaxon/Downloads/plexmediaserver_1.3.0.3059-6277334_amd64.deb
Nov 27 16:51:24 ubuntu org.debian.apt[755]: 16:51:24 AptDaemon [INFO]: InstallFile() was called: /home/jmaxon/Downloads/plexmediaserver_1.3.0.3059-6277334_amd64.deb
Nov 27 16:51:24 ubuntu AptDaemon.Trans: INFO: Queuing transaction /org/debian/apt/transaction/0960f3d788f84ffb999e38cb0d4efd4b
Nov 27 16:51:24 ubuntu org.debian.apt[755]: 16:51:24 AptDaemon.Trans [INFO]: Queuing transaction /org/debian/apt/transaction/0960f3d788f84ffb999e38cb0d4efd4b
Nov 27 16:51:24 ubuntu org.debian.apt[755]: 16:51:24 AptDaemon.Trans [INFO]: Queuing transaction /org/debian/apt/transaction/0960f3d788f84ffb999e38cb0d4efd4b
Nov 27 16:51:24 ubuntu AptDaemon.Worker: INFO: Simulating trans: /org/debian/apt/transaction/0960f3d788f84ffb999e38cb0d4efd4b
Nov 27 16:51:24 ubuntu org.debian.apt[755]: 16:51:24 AptDaemon.Worker [INFO]: Simulating trans: /org/debian/apt/transaction/0960f3d788f84ffb999e38cb0d4efd4b
Nov 27 16:51:25 ubuntu AptDaemon.Worker: INFO: Installing local package file: /home/jmaxon/Downloads/plexmediaserver_1.3.0.3059-6277334_amd64.deb
Nov 27 16:51:25 ubuntu org.debian.apt[755]: 16:51:25 AptDaemon.Worker [INFO]: Installing local package file: /home/jmaxon/Downloads/plexmediaserver_1.3.0.3059-6277334_amd64.deb
Nov 27 16:51:27 ubuntu AptDaemon.Worker: WARNING: An additional step to open the cache is required
Nov 27 16:51:27 ubuntu org.debian.apt[755]: 16:51:27 AptDaemon.Worker [WARNING]: An additional step to open the cache is required
