Check Songs on Work Computer with iPhone

Hello,
I have my iPhone synced with my home computer and I play the songs on my work computer. No transfering, just plug in and play on iTunes. Here is where I am having issues, when I start playing a playlist, if the song is not checked it will skip it (or in the case of some playlists none are checked and it will only play the one I double click). How can I check other songs to be played? Although I click the little box to get a check mark while at work - they never appear.
Has anyone else had this problem? What can I do to fix it?
Thank you,
Perr8727

First I dont have speakers to plug into the phone, but beyond that - why would some work and not others? I obviously can do what I want, but for some reason not all are working correctly (or I am not doing it correctly for them all to work). My phone is more than backed up, so I am not worried about an accidentaly wipe.
My company supplies iPhone for us, and my coworkers are not having this same issue - so it must be something I am not doing that they are.

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