Can you run an entire iTunes playlist on gapless playback?

I have a specific "party playlist" and I want all the songs on it to run gaplessly as though they're all part of a mix. I have "Crossfade songs" disabled but it still won't work. When I was first creating the playlist and testing out the playback, the songs DID play without any gaps but now there are gaps and I can't seem to get it to go back to playing gaplessly.

my understanding is that crosfading is what makes the songs overlap by 1-12 seconds, so the end of the first song has the begining of the second song playing as well. i.e. setting the crossfade to 6 seconds (middle of the slider) would play the last three seconds of old song and first three seconds of new song at the same time..
In short, try ENABLING crossfading, then playing with the preferences.

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