It’s quite funny, because last weekend I performed an upgrade from 11.3 to 11.5 and ran into a very similar issue—one that was later described in the article ArcGIS Server Upgrade Step 2 of 2 Fails with Error, "Refresh Auto-Deployed Services during, which was published after I had already fixed the problem on my own.
In my case, however, the issue affected the OfflinePackaging service rather than CachingTools.
In the ArcGIS logs I saw the message:
A JSONObject text must begin with '{' at character 1 of
while the upgrade process reported:
ArcGIS Server upgrade step 2 of 2 fails with error, "Refresh auto-deployed services during upgrade".
It turned out that the file:
arcgisserver\config-store\services\Utilities\OfflinePackaging.GPServer\esriinfo\lifecycleinfos.json
contained values NULL instead of the objects inside {}.
I replaced the content of lifecycleinfos.json with {} and, after saving the change, I re-ran the upgrade—this time it completed successfully.
I’m not sure whether installing the patch ArcGIS Server Security 2025 Update 2 Patch before the upgrade would have resolved my issue as well.
Good luck
Mariusz
www.linkedin.com/in/mariuszzarzeczny