Trim Clip Removal

Is there any way to make this process more painless? I have tried numerous different trim tools with the same result.
I have a Dakota. I feel your pain.

My less-painful process is:
1.) cut it off at the head and punch in the rest. (Fine for chassis, maybe not so great for interior where it might rattle around.)
2.) Keep a big selection of Amazonian sourced replacements in stock.
 
I am not a fan of the style pictured. I’ve busted a few knuckles trying to get those out lol. My favorite tool to use on any of the plastic fasteners is the Matco made by Mueller Kueps clip lifter tool. My boss showed me it and I haven’t looked back since and now just about everyone in my shop has one. They also make angled ones too. Very handy tool. Best tool for any of them in my opinion. But yes the ones you are referring to are very hard to remove. Usually once I get those out about a quarter or half way I grab them with a set of pliers and just replace them. We keep them on hand at work. Luckily being a Subaru and Toyota guy I don’t run across them a whole lot. The ones they have are slightly better but often the little pegs in the bottom will separate.
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Get yourself some silicone spray.
And what, pre-spray them before yanking?

I agree with OP, hate these things.

I actually stated filing them down a bit before installing. No real issue with grip, just much easier full insertion, and removal as needed.

It’s so easy to damage things when trying to remove these clips.

 
And what, pre-spray them before yanking?
I try to lift them just enough to get the plastic straw underneath so a little bit of silicone can leak underneath. On my RAM 1500 this helped a lot, inside and out. Especially when I installed plastic fender wells (no, not the ridiculously big ones).
 
I use a pair of angled wire cutters like the kind Snapon sells for pulling cotter pins. I buy various sizes of those clips in bags of 100 on Amazon to replace ones that dont survive
 
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My Ram pickup uses a lot of these trim clips. These clips are extremely difficult to remove and they are always slightly damaged after even just one r/r. Is there any way to make this process more painless? I have tried numerous different trim tools with the same result.

(Most of my experience is with Asian vehicles and they do not use this type of clip?)
Yep they all do that....even if you pull it right back out.
 
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