I recommend boring out the rear two mounting holes on the front fender to raise the rear portion of the fender a tad but the best way to check is to get a 5/16" nut and tape it to the center of the tire and spin the wheel and listen to see if the nut scrapes the inside of the fender. If it does not scrape you are good. if ti does bore out the rear two mounting holes.
When you put the fender back on hold up the back of the fender as you tighten the rear two bolts as this creates a little bit of additional clearance.
Some vendors advise that there is no need to do this but I have seen issues with tires rubbing fenders on all year Glides with all different brands of tires so I recommend taking the time to check this.
Do it!!! I was drinking when I installed my wheels and this time I didn't do it! Last two times I drilled holes and guess what I have a racing stripe on rear side of fender where paint bubbled! I have new fender and I drilled holes! Now I have spare fender with racing stripe
I changed to a 21 also and the only mod I did was that recommended hole enlargement of the rear bolt holes. Worked out great. Why take the chance or damaging the paint if ya don't have to? I think the fender looks better with a 21 under it also.
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