[quote=firescue17 post_id=470449 time=1594755762 user_id=108732]
[list][*]Check for updates leads to the download page.
[*]The only download is the full .exe.
[*]Running the .exe in the same location with the same installation settings wipes the previous install. The .ini settings are wiped. The playlists are wiped. Everything. Everytime.[/list]
[/quote]Yes, yes and no. This is how updates are done and it works. Something went wrong with your install and it this point there isn't enough information to know what.

It's not possible to update in place.
[list]
[*]Check for updates leads to the download page.
[*]The only download is the full .exe.
[*]Running the .exe in the same location with the same installation settings wipes the previous install. The .ini settings are wiped. The playlists are wiped. Everything. Everytime.
[/list]

This is not how it normally happens. It may mean that:

1) You installed in a different location
2) You installed it differently (portable vs. regular install)
3) You uninstalled the old version, then installed the new version
4) Settings are in a different Windows User account: http://www.mediamonkey.com/support/index.php?/Knowledgebase/Article/View/123/0/mediamonkey-settings-lost

Your Library should still be on your PC. Do a search for mm.db (make sure to include hidden files) and then replace the new database with the old one. Database default location: https://www.mediamonkey.com/support/index.php?/Knowledgebase/Article/View/16/0/modifying-the-mediamonkey-db-and-ini-files This would recover the Library, your settings may be lost.

What kinda .exe file wipes every single .ini file when upgrading?
Why is there no option to upgrade a remote installation in place?

MediaMonkey Gold for years now ... every single time I upgrade it wipes all my cover images, play counts, playlists, ... every single thing I've spent 1000s of hours tweak gets wiped. Every. Time.

Please. Stop. It.