It runs really poorly on Windows if you have a large library , even if you don ' t its font rendering can be insane I can barely read the iTunes Store seemingly at random a lot of people have this issue on the forums but no one ' s sure what causes it , and when it fails at things it often fails totally silently no error messages , nothing informing you , you just find out that a video failed to copy because , as you discover after an hour of investigation , the metadata atom was 6 bytes too long though the file played fine on Android . You can ' t use iTunes if anyone else on your machine has iTunes open , so if you share a computer with SOfamily , you ' ll be calling them over to log you out , log in , close their iTunes , log back in , etc . Oh , your girlfriend was trying to stream video from her iTunes ? Sorry , stop watching TV , I need to put an album on my phone . And it ' s a huge resource hog with memory leaks it ' ll use ~ 10 times as much RAM as rivals like MusicBee , even if you ' re just playing music in the background . More generally , the model of having to sync stuff up can just be really irritating compared to the simplicity and reliability of copying files . I really like iOS and iPhones , but tying it to iTunes is a huge headache and makes me reconsider my next purchase . It ' s kind of the classic example of an application intended for one purpose that fell victim to feature creep , awkwardly forcing in more and more features until it became a sloppy monster .