https://bugs.winehq.org/show_bug.cgi?id=57010
--- Comment #26 from Esme Povirk madewokherd@gmail.com --- Here we go. referencesource indicates this is a special case: https://gitlab.winehq.org/mono/mono/-/blob/main/mcs/class/referencesource/Sy...
Seems System.Windows.Forms.ApplicationConfigurationSection is handled by System.Configuration.AppSettingsSection.
.NET Core winforms has no reference to AppSettingsSection, so yes, this was likely removed before the open source release.
I guess the first step would be to port this special case to Mono's System.Configuration, which should be enough to prevent the error. Then our fork of .NET Core winforms should be updated to actually use the "DpiAwareness" key.