Playlist is not transferred to iPhone

I am trying to transfer a playlist on my iPhone 4 (with iOS6) and it fails (all the songs are shown greyed-out with a strange symbol on the left, see attached image). I have not enabled itunes match on the iphone and I am managing music manually. Also I have plenty of space in the iPhone.
Thank you

Same issue here. Made playlist in iTunes 11 on my windows XP machine, tried to sync to iPhone 4S running iOS6. Saw the playlist on the phone, saw the songs, but just get the "I may load someday" ying-yang symbol.
Tried to drag the songs over individually, but that didn't work either. Restarted phone entirely, but still same issue. normal sync of songs that I dragged into phone, that were not a part of the playlist also did not want to load, but after a couple sync tries, they did eventually transfer to phone. Playlist still didn't transfer even after the other songs worked.
I am also managing music manually and have Match disabled.

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Hi PeterleD,
Thanks for visiting Apple Support Communities.
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http://support.apple.com/kb/ts4054
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The minimum requirements for your Mac for an iPhone is Leopard 10.5.8.
iPhone minimum requirements:
Mac computer with USB 2.0 port
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iTunes 10.1 or later (free download fromwww.itunes.com/download)
iTunes Store account
Internet access
You will have to upgrade to Leopard if your Mac meets v10.5 minimum requirements in order to sync, restore, or backup an iPhone.
Requirements for Mac OS X v10.5
iPhone 3GS Tech Specs: http://store.apple.com/us/browse/home/shop_iphone/family/iphone?mco=MTAyNTQzMjI

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