Play list in iCloud does not update when I change it on my computer

I have a play list that I have  been adding songs to. (runs are getting longer) The problem is even if I click on the update iTunes match in iTunes the added songs do not appear on my other devices. In particular my iPhone. The play list on my phone still shows the old song count the playlist originally had. How can I get these songs to show up on my phone...I have 4 days to get this figured out before the marathon...

3rd generation iPods don't charge over USB.

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