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How to stop automation from playing the same track back to back?

I'm new to using PlayIt Live and I am trying to use automation to keep something playing between scheduled broadcasts. I have a limited number of tracks right now, each about an hour long from a few different radio shows. I keep noticing that it often places either the same track or something from the same show back to back. adding more tracks seems to have reduced this occurrence but is there any way to stop it from happening completely?

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