http://bugs.winehq.org/show_bug.cgi?id=19074
--- Comment #6 from Scott Ritchie scott@open-vote.org 2009-06-26 01:30:08 --- The usual place (and reason) for a user seeing this error is the program not being in the current directory - although you are right that we search the full PATH (as well as the system32 folder). Perhaps:
wine: could not load "itunes.exe": the specified program was not found in the current directory or system path
Windows error message unfortunately appears just as unhelpful (not telling you "wrong directory")