Sounds very much like a warped brake rotor.
Front Brake Vibration
I own a 2001 Heritage Softail Classic with 27,000 miles. Recently developed vibration when applying front brake at highway speeds. Under 30mph seems okay. Anyone have any experience with this? Brake pads seem ok. Possible brake rotor warpage? Front brake has always seemed to drag a little when pushing bike while not running. Thanks for any feedback.
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Yep, you have a slightly warped rotor. It is common with the '00-up rotors. You can use a dial indicator and a rubber mallet to knock 'er back straight and get many more miles out of the rotor.
Went through it on mine. They tried both rotors in stock and they were out more then the ones on that were giving me problems! As it was warranty work I ended up paying the difference in price for a set of floaters and could not be happier.
While all the above is true, you might try breaking the torque on the bolts and resettiing them properly.
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