Transferring iTunes store song to 3rd gen ipod

I just downloaded a song from the iTunes music store and then tried to transfer it to my husband's 3rd gen iPod. I received a message saying that I needed to d/l the newest iPod Updater software, which I installed. I received the same message when I tried to transfer the song again. I re-installed the software and received the same message again. I have purchased music from the iTunes music store and transferred it to this iPod in the past so I don't know what could be the problem. I would welcome any help anyone can offer. Thanks!

After installing the iPod software on your computer, open the most recent version of the iPod updater in your /Applications/Utilities/iPod Software Updater/ folder, and click the Update button when the iPod is connected to your machine. Follow the onscreen instructions to complete the update procedure.
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