Help!! I-tunes will not allow me to transfer purchased songs.

My computer crashed and I lost everything and had to start from square one. I followed the directions from another posting and downloaded the suggested software program for Windows (Tune Jack) that allowed me to transfer everything that was on my Ipod back onto my computer and into my I-tunes library.
Next I added a few new Podcasts and downloaded a few new songs. Then I went to sync my Ipod and it would not transfer the new songs and all my past purchases from the past few months back onto my Ipod and effectively erased them from my Ipod. The message was that they were "not authorized to be played on my computer." However they still remain in my I-tunes library, just not on the Ipod any longer.
How do I get them back on the Ipod like they were before?
Very frustrated. Thanks for any help.

try playing one of the songs in iTunes prior to trying to sync them to the iPod.
what most likely happened, is you did not authorize the computer to play stuff from your itunes store account.

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Stephenm52 wrote:
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2 users, (2) iPhones and Mac Book Pro and Mac Book Air and a Windows PC
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Help!! I-tunes will not allow me to transfer purchased songs.

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