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> Unbeknownst to me, iTunes triggers a reshuffle when I do that, and the very next track to play is the one I was trying to get away from.

What are the odds of this happening?

Pretty low if I'm listening to all my music at the same time, but what if I have a playlist of 10 songs?

> Pretty low if I'm listening to all my music at the same time, but what if I have a playlist of 10 songs?

You wouldn't listen to a playlist of 10 songs when there are many of them in it you are not in the mood for?

Well, you only need one for it to be annoying!

Just about every album I have has one song that I will routinely skip over, because I don't like it much.

Yeah, sometimes I like to just toss a album in a playlist and listen to it, and I always seem to end up skipping at least one song

Then un-tick it.

Or rate it poorly and factor ratings into your smart playlist.

And further that could be guarded against fairly easily. Reshuffle would exclude the last ten songs from being the next ten songs, etc.