1.27.2.5929 to 1.41.8.9834 Should I?

Server Version#: 1.27.2.5929
Player Version#:
<If providing server logs please do NOT turn on verbose logging, only debug logging should be enabled>

I’ve been on 1.27.2.5929 for a long time. I have a very large music library on iTunes that I transfer to Plex. I’ve avoided upgrading because of the large number of complaints in the past. What should I be aware of to upgrade now?

3 years of updates will be a lot to catch up on, plus the Windows version went 64 bit.

Make backups of the database files (w/Plex not running)
People will always complain
Have this ready to go: GitHub - ChuckPa/DBRepair: Database repair utility for Plex Media Server databases

Let it rip!

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I would even say, execute it before trying the upgrade.

Thanks for the kind help and advice from everyone who replied. I’m already on Windows 64 and given that there’s nothing I absolutley need on my present server version, I think I’ll avoid unnecessary headaches and stay where I am. Thanks again.

If you want the use the Plex mobile apps (and in a few weeks the re-developed Android/Roku/smart TV apps as well), you need to be at least on PMS 1.41.2.
So you might as well prepare now.

For the record, I went from 1.19x to 1.40.5 without any issues. I would have stayed where I was except that I knew some of my users would not be able to delay the client updates, and then wouldn’t be able to connect to my server. As @OttoKerner said, if you want remote access via a client app, you’ll have to update anyway. I’m running 1.41.6.9685 on my Windows server with no issues,

I took a full backup before I went ahead with the upgrade, of course in case I needed to revert.

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