Recently I had experience the same problem, and I wrote to Nike+ the following message:"09/17/2009
Hi, after upgrading my iTunes to the latest version(9.0), my runs are not showing in the Nike+ web. I see the runs in iTunes, but they are not transferred to the web. Any known issues with this new version?
Thanks"
They sent me a step-by-step guide and I finally uploaded my runs. Here it is. But still I have problems with Facebook (the problems started after updating to the new version of iTune),Facebook do not sync with Nike+ most of the time now.
--"Here are the steps below, if at anytime you would like to troubleshoot over the phone, please call us at 1-800-379-6453 option 3. We're open 7 am to 4 pm PST 7 days a week.
1) Dock your iPod nano. When iTunes opens go to the Nike + iTunes tab.
2) Un-check the check box to "Automatically send workout data to nikeplus.com" and click Apply.
3) Safely un-dock your iPod nano.
4) Go for a run or short test workout. Around the room is fine. Just enough to register a distance on the iPod nano.
5) Dock your iPod nano, then select the check box to "Automatically send workout data to nikeplus.com" and click Apply at the bottom-right of the screen.
6) iTunes will make the connection to nikeplus.com and send the workout.
Note: At this point, the workout is not attached to your account.
7) In iTunes, the button to "Visit nikeplus.com" should be displayed (you may be presented with a window to either "Visit" or "Don't Visit"). Click on Visit and your default internet browser should open and go to nikeplus.com.
8) Your workout is visible, but it still is not attached to your nikeplus.com account. Log in to nikeplus.com and the workout will attach to your account.
9) Close the browser window. It does not matter if you log out or not.
10) Go back to iTunes and click on the button, "Visit nikeplus.com." Your web browser should open, but you can close it immediately.
11) Go back to iTunes. Your email address should appear below the "Automatically send workout data to nikeplus.com" check box and the options Cancel and Apply will appear. Click Apply to save this setting.
All future workouts will automatically upload to the appropriate nikeplus.com account".