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As long as you are following the instructions properly, I would say you have a defective board. This accessory is notorious for failing even brand new straight out of the box. In fact, they are so unreliable that most consignment game shops will not even consider purchasing them from you.
If you are simply finding it difficult to connect the board because you lack the proper instructions, here you go: How to sync Wii Tony Hawk Ride Skateboard (not my vid, but this is exactly what you need to do).
IT TOOK 1.5 HOURS TO SYNC UP AND CALIBRATE A NEW TONY HAWK RIDE SKATE BOARD WITH A Wii. THE ON-LINE DIRECTIONS AND TROUBLESHOOTING = SUX!. PLEASE FOLLOW THESE DIRECTIONS IF YOUR HAVING THE SAME ISSUE: 1) Remove skateboard battery's for 1 minute 2) Reinstall 4 new/fully charged AA Battery's in the Tony Hawk RIDE Skateboard. 3) Plug the Tony Hawk Wireless USB Dongle into the "upper" WII USB Port, Turn on the WII, Insert the Tony Hawk Ride game disk Keep pressing A on the WII Controller till you get to the Error Screen saying: *Unable to SYNC up the skateboard with the WII* 4) Make sure the WII and the plugged in wireless USB Dongle are laying on the floor in front of the wireless skateboard "sideways" with the wireless dongle towards the right side of the WII. 5) The directions state to 1st press the wireless USB dongle reset/Sync button, then the so called Start button on the board, which did not work 100 different times. 6) Instead (on the side of the board) all 4 of the blue LED lights were on. Now press and hold the button which is the Start/Home/blue little house/C- looking Button on the side of the board for 5 seconds. The Blue LED lights should now all be off! 7) Now press the WII Wireless USB Dongle reset/Sync button. 8) After the Dongle sync
IT TOOK 1.5 HOURS TO SYNC UP AND CALIBRATE A NEW TONY HAWK RIDE SKATE BOARD WITH A Wii. THE ON-LINE DIRECTIONS AND TROUBLESHOOTING = SUX!. PLEASE FOLLOW THESE DIRECTIONS IF YOUR HAVING THE SAME ISSUE: 1) Remove skateboard battery's for 1 minute 2) Reinstall 4 new/fully charged AA Battery's in the Tony Hawk RIDE Skateboard. 3) Plug the Tony Hawk Wireless USB Dongle into the "upper" WII USB Port, Turn on the WII, Insert the Tony Hawk Ride game disk Keep pressing A on the WII Controller till you get to the Error Screen saying: *Unable to SYNC up the skateboard with the WII* 4) Make sure the WII and the plugged in wireless USB Dongle are laying on the floor in front of the wireless skateboard "sideways" with the wireless dongle towards the right side of the WII. 5) The directions state to 1st press the wireless USB dongle reset/Sync button, then the so called Start button on the board, which did not work 100 different times. 6) Instead (on the side of the board) all 4 of the blue LED lights were on. Now press and hold the button which is the Start/Home/blue little house/C- looking Button on the side of the board for 5 seconds. The Blue LED lights should now all be off! 7) Now press the WII Wireless USB Dongle reset/Sync button. 8) After the Dongle sync
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