https://bugs.winehq.org/show_bug.cgi?id=42254
--- Comment #8 from winetaste@gmx.net --- (In reply to winetaste from comment #7)
The same for every version of iTunes up to 12.10.10.2 (last for Win7/8.1). With the newest one (12.11.0.26*) this is fixed/a different bug.
Different behavior is result of (forced) Win10 setting and not the iTunes release itself. Same for older releases.