http://bugs.winehq.org/show_bug.cgi?id=26835
--- Comment #129 from john_p_turner@yahoo.com 2011-05-14 22:38:17 CDT --- This has got to be something with signatures of files and validation. After updating portal 2 in ubuntu and booting back into windows I got the crash at main menu like on linux. So upgrading in one system prevents the other system from using.