You can save yourself alot of time and aggravation with a very simple solution I found that worked quite well. Before you even get started take the screw and nut to a good hardware store. Replace the screw with a SS phillips or socket head screw and reuse the original nut.

The problem with Harley's design is the screw. It simply doesn't have a large enough head and deep enough slots to provide enough leverage to close the ring gap without the head pulling through or stripping out the slots.

I found that almost all standard screws that thread into the stock nut will have a larger (better head) that will pull the gap together very nicely. A simple $.25 investment will make this job take but a few moments to install correctly each and every time.

 

I considered that idea too. The only reason I didn't go with it is because I couldn't find an allen head screw, that would fit, at my local hardware store.

 

It really shouldn't be that difficult to find. I believe its 1.25 or 1.5 inches long with fine threads. I would recommend getting it in stainless steel. I think I bought mine at Lowe's.

 

It wouldn't have been hard to find if I had of been at work. We have 1000s of them there but I wasn't at work..lol. I may still change mine after I can locate one. Using the clamp to help close the gap, the phillips worked just fine.

 

Good idea but I got the same results (no gap between the 2 ends of the trim ring) without using clamps. I loosened the stock ring bolt, mounted the trim ring over the stock ring, and tightened both bolts alternatively until both ends on the trim ring touched. This was easy.

But this doesn't solve the other issue. The remaining issue is that the trim ring sits away from the headlight glass. It leaves a 1/4" gap all around the glass allowing dust, bugs and water between the headlight and the trim ring.
From your pictures, it's the same for you.

Anyone has been able to mount the trim ring so that it contacts the headlight glass all around the perimeter? What did you do? I tried to loosen the adjustement bolts to no avail.
Note that there's no gap whatsoever with the passing lamps and turnsignals trim rings.

This headlight trim ring is very poorly engineered and I'm being nice when I say this.

 

The gap between the ring and the glass is more related to how you have the headlight adjusted. You can eliminate the gap by adjusting the up/down or left/right adjustment screw although you may not like the end result of the lighting on the road. I wanted my lighting up higher than it came stock from the factory/dealer. I adjusted the bulb upward which may have impacted the gap between the trim ring and glass. Overall, I very much agree that this is just another poorly designed accessory from HD. About the same poor quality as the design of the oil temp gauge accessory.

 

I think everybody has tried this the same way you did it but not with the same results. The way you did it is how the HD instructions say to do it and apparently, it works for some but not for all...me included.

The gap you speak of between the headlight glass and the ring does exist but the original ring on mine feels that gap preventing critters from entering or, at least, it prevents them from entering into the headlight bucket.

I have read where other folks have filled that gap with silicone and some have used insulating tape.

I think we are all in agreement that the design, of these rings, is a turd.

 

Put some spacers (washers) behind the retaining headlight ring which will bring the light out. At least in my case the trim ring was hitting the fairing and the headlight set back.

 

I like that idea. May give that a whirl. By the time I get all the kinks out of this one, HD will probably have a new design that actually works...lol.