Unless the updates really uninstalled the application instead of just breaking it, and that's really (another) bad decision from Microsoft.
Unless the updates really uninstalled the application instead of just breaking it, and that's really (another) bad decision from Microsoft.
Windows' upgrade process could in theory disable the shell extension, but that would be even worse than uninstalling the program given how programs on Windows do not take kindly to being 'half-installed' (case in point: uninstallers that break when some application files are removed).
This is what backwards compatibility leads to, and there is no way all parties can win in this scenario.
Note also that I don't especially consider Classic Shell to be an odd program given that when I briefly worked at Microsoft a few years ago (Win 8.1 was current), my manager actually recommended I install it on my second day there on the company-provided computer in order to retain the classic UI because that group found the Win8 touch UI to be unusable on the desktop.