What is the problem?
Dropping multiple files on the UI to overwrite existing files only uploads the first file.
What did you already try to solve it?
Not really a solution, but delete files before dropping replacement files.
Have you tried running in safe mode?
No
Did running in safe mode solve the problem?
didn't try.
Systeminfo Bundle
You can download this in OctoPrint's System Information dialog ... no bundle, no support!)
got the sys info budle, but not sure what to do with it.
octoprint-systeminfo-20211029080050.zip (1.9 MB)
Additional information about your setup
OctoPrint version, OctoPi version, printer, firmware, browser, operating system, ... as much data as possible
Running windows 10 and using a Chrome browser. Octoprint 1.7.0