Randomly now, no matter what I do, I receive ‘operation failed’ whenever I try to update the server to a new version. Im not sure if its a Synology issue or a random issue now with Plex. I ended up reinstalling Plex, and am now stuck Version 1.10.0.4523. I used to be on the latest Beta version.
NAS: DS716+II
DSM 6.1.5-15254
It’s not a known issue with PMS. I tested with DSM 6.1.5-15254 as soon as available.
Try this:
Apparently Safari is acting up, not really sure what is going on with Safari and DSM login. I used Firefox Quantum/ver. 57, and it worked flawlessly. Sorry to make an erroneous post and appreciate the VERY quick reply and support.
Not to worry. That’s what we’re here for. It working is what matters!
This is happening to me on Firefox Quantum 59 beta too…
Use of beta anything is at the user’s risk.
I deinstalled Plex as suggested above. Then I did a manual install with the latest plex version (beta) with firefox. This worked. Earlier installments with safari / chrome failed.
Hi
I was having trouble like this and I found that Safari and Chrome were not performing correctly when downloading updates for Plex and trying to restore configuration files.
I installed the latest Firefox and did all updates etc… using the Firefox browser instead of Safari or chrome and everything worked perfect.
Now all I need is a hair transplant to replace the hair I lost these last two days.
I have some extra gorilla glue if needed. 
Hi @ChuckPa
Hope it’s okay to bring up an old thread as I am experiencing exactly this and I can’t make it work. Not too sure what version I was on, I’m updating regularly, but trying to upgrade to any of the .19xx versions was returning “Operation failed.”, even after skipping a version, even after trying with other browsers (Firefox shouts the error without even uploading the file!).
The steps above were executed: stopped, uninstalled, rebooted, attempted to install - nothing. Looking at https://forums.plex.tv/t/synology-faqs-read-this-first/274891#Q11 the Plex user and its home folder were deleted, and connecting by SSH confirmed none of the following exist:
/var/packages/Plex Media Server
/volume1/@appstore/Plex Media Server
/volume1/Plex - it’s there but I’d like to keep it!
Any idea how to make any progress?
What permissions does the Plex folder need, does admin need access or does any synology internal service need permissions too?
Thanks!
[update]
Installing by SSH as root just worked fine, and Plex is up and running again. Any cons in doing this 
?
There is something else which stops the package and results in Operation Failed.
If there’s a problem with the shares / directories, I will popup a “Damaged” window.
Youre seeing a failure to start. Manually grabbing the Logs directory,
(File station - Right Click - Compress to Logs.zip) and attaching that here will let me see what it doesn’t like.
First choice:
In Control Panel - Shared Folders - Permissions, user Plex has full control.
Last Resort:
/volume1/Plex gets sudo chown -R plex:users /volume1/Plex if you’re going to override by hand.
Supplemental to the above,
As of PMS 1.15.4.994, you’ll find I removed Plex from the admin group.
It’s no longer needed and increases media protection against accidental deletion.
Direct result of this is you’ll manually need to give Plex permission to read your media shares.
I made a Community Announcement which has been referenced in multiple threads.
(Security changes for Synology users)
Thanks a lot for the insightful replies, much appreciated!
I am happy to share the Logs.zip but rather privately, happy for me to send a PM with a diskstation link?
Re. the Plex folder permissions, unfortunately that is exactly what was checked before re-installing, and the plex user had either the “full control” (all ticked, including taking ownership etc.), or read-write permissions, however this did not allow the package to install, still. Once I followed the docs, advising to remove the plex user altogether, that also did not work. I can see in the installation it does set this permission for the plex user also, so my feeling was that actually the error was happening before that, given nothing like that was in the logs as usual during an installation. Regardless, I also have the gut feeling permissions caused this somehow, due to the fact I have been re-checking and re-setting many permissions lately, and that is the major change before the installations failed.
[edit] To gain some more insights on this one, I have attempted to re-install from the GUI and the result is the same, Operation failed. Plex runs okay in the meantime, and streams with hw transcoding too!
[/edit]
I have been really proud of your previous announcement on the plex user coming out of the admin group, I have followed all the conversation before that closely and I have massively appreciated the effort and result, as that is what I really wanted to achieve for the security of the whole DS, but failed to, for long 
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