http://bugs.winehq.org/show_bug.cgi?id=15053
Summary: for some apps wine update forces reinstalls Product: Wine Version: 1.1.3 Platform: All OS/Version: Linux Status: UNCONFIRMED Severity: normal Priority: P3 Component: -unknown AssignedTo: wine-bugs@winehq.org ReportedBy: bluedzins@wp.pl
It applies not for all applications. It is not only the problem with current version of Wine, because it happened before.
Take for example Great PWN Dictionary -- you install wine, you install this app, everything works fine. But when you update wine something is changed in that way that this app is corrupted and it (not wine) says the installation was not successful, reinstall is required. After reinstall everything is fine again until... next wine update. And so on.
I know there is not much details here, please ask what should I add, I will help for sure.