It looks like Plex may have an error in their plexmediaserver.service file for systemd, I found this error in my syslog file:
Mar 13 20:37:10 NAS systemd[1]: [/lib/systemd/system/plexmediaserver.service:11] Invalid escape sequences in line, correcting: "/bin/sh -c 'LD_LIBRARY_PATH=/usr/lib/plexmediaserver /usr/lib/plexmediaserver/Plex\ Media\ Server'" Mar 13 20:37:10 NAS systemd[1]: [/etc/systemd/system/plexmediaserver.service.d/override.conf:1] Assignment outside of section. Ignoring.
No, That’s a hand-crafted (human created) service override file with bad information in it.
Something there attempted to override the default service file and did so incorrectly.
It is complaining at line 1. This implies the format of override.conf is not per systemd requirements.
I’m having this same issue after upgrading to 1.4.3:
Mar 15 11:37:32 plex systemd[1]: [/etc/systemd/system/plexmediaserver.service:11] Invalid escape sequences in line, correcting: "/bin/sh -c 'LD_LIBRARY_PATH=/usr/lib/plexmediaserver /usr/lib/plexmediaserver/Plex\ Media\ Server'" Mar 15 11:37:32 plex systemd[1]: Started ACPI event daemon. Mar 15 11:37:46 plex systemd[1]: Reloading. Mar 15 11:37:46 plex systemd[1]: [/etc/systemd/system/plexmediaserver.service:11] Invalid escape sequences in line, correcting: "/bin/sh -c 'LD_LIBRARY_PATH=/usr/lib/plexmediaserver /usr/lib/plexmediaserver/Plex\ Media\ Server'" Mar 15 11:37:46 plex systemd[1]: Started ACPI event daemon. Mar 15 11:37:46 plex systemd[1]: Starting Plex Media Server for Linux... Mar 15 11:37:46 plex systemd[1]: Started Plex Media Server for Linux. Mar 15 11:37:47 plex systemd[1]: Reloading. Mar 15 11:37:47 plex systemd[1]: [/etc/systemd/system/plexmediaserver.service:11] Invalid escape sequences in line, correcting: "/bin/sh -c 'LD_LIBRARY_PATH=/usr/lib/plexmediaserver /usr/lib/plexmediaserver/Plex\ Media\ Server'"
I will look at why the latest Ubuntu update is being so pedantic. It’s always being odd man out.
As you see, it’s correct it to its liking but not fatal.
Yet another Ubuntu PITA. 
@ChuckPA said:
No, That’s a hand-crafted (human created) service override file with bad information in it.
Something there attempted to override the default service file and did so incorrectly.
It is complaining at line 1. This implies the format ofoverride.confis not persystemdrequirements.
There are two errors:
- The first error was probably something I did incorrectly trying to override the file creation mask.
- The second error looks to be a formatting error that belongs to Plex.
I believe this is the line:
ExecStart=/bin/sh -c 'LD_LIBRARY_PATH=/usr/lib/plexmediaserver /usr/lib/plexmediaserver/Plex\ Media\ Server'
Is the backslash escaping of the space the issue since it is enclosed in single quotes?
Reed, that’s the goofy part.
You are correct, we need to escape the spaces because they are part of the file name "Plex Media Server" but we can’t use both single and double quotes in the ExecStart because it breaks all the other systems which use SystemD.
What gets more insulting is the service definition file was last changed Jul 15, 2016
It was changed to be compliant with the Bash and SELinux changes implemented by Ubuntu. Their ‘further enhanced’ security. (they don’t allow LD_LIBRARY_PATH to be passed as an environment variable now… it MUST be on the command invocation line with the the executable.
IMHO, at the current rate, I will start telling everyone to turn SELinux OFF. It’s been nothing but trouble for me since day 1 for precisely this reason. This is Linux, not Windows nor OS X. When I do something as root, the machine should not second guess what it thinks I meant to do and then say “NO, you can’t do that”.