Shortly after purchasing my fiance's 98 classic cherokee (red with black fender and side trim), we took off the black plastic to paint it as it was faded and gray.

That was months ago. The rear fender trim still isnt on.

Has anyone here had trouble getting them on and thus have any advice to share? Much appreciated.

 

I think you'll find a lot here say to leave it off, that it looks better. You'll need good double sided tape and maybe something to lean against it that is heavy. Next time I'd just tape it off and paint it on the jeep.

 

I would, except, this model is the kind that has the steel trim bracket riveted to the jeep. Right above the rear wheels. It functions as a sort of clip-- however, it's nigh impossible to get back on. But leaving it off is rather ugly.

 

It's not riveted. It uses pass through bolts that tend to be extremely rusted and like to break. Use a bunch of PB Blaster on them and loosen them up a little. From there, the flare can go back on, then tighten the bolts back up to get the flare flush with the body. That's the tough way. Easy way is to just trash the metal brackets all together and like Red82 said, use some good 3M double sided tape to stick the flares back on the fender after you've really cleaned it up so there's nothing to keep the tape from adhering really well.

 

I agree except with the 3m tape part. I tried this on my 98 and after taking all the time to remove any wax and dirt they still only stayed on for about a month. I ended up buying some stainless steel nuts and bolts. Grind off the old bolt and replaced with the new. It work fine.

 

Are you talking about the rear bumper caps? or the rear fender flares?

I took mine off to paint and they just slid right back on. Slide from the rear to the front and then screw down tight. Flares screw on along the wheel lip.