Not all songs in an album played when shuffling them

Ok, so I searched for info on this and can't find any questions that ask about the exact same issue...
If I select an artist (multiple albums) or an album and try to play all their songs (or all the album's songs) in shuffle mode, if I try to start off by playing any song other than the first one in the list (ordered by track number), then they all won't play. I've tried both selecting the starting song, then hitting shuffle, as well as hitting shuffle, then selecting the starting song.
When you turn on shuffle, what actually happens? Do the songs the "re-ordered" randomly every time you turn shuffle off then back on? If so, how do you get the song you have currently selected to be the first one in the list?
Greg

I have experienced the same thing for months now and was in false belief that there was something wrong with my songs. iTunes should go through all songs and play them randomly. There is absolutely no excuse for this not to work properly. Repeat option is completely separated. It's purpose is to play songs indefinitely. It shouldn't be necessary to turn repeat on for iTunes to play all songs while shuffle is on.
I will just never be able to comprehend how is it possible for people who make this software for years not to see this problem while they test the application (if they do that at all) and fix it. This is just ridiculous and pure nonsense.

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