Sounds like the problem is in the finish nail head---there should be a small divot in the nail head---to align the nail set point.

Now, if you bent a nail set, I'd like to know where you got that set----since I have never seen a nail set that was bendable.

And, what kind of hammer are you using? A regular carpenters claw hammer? If not, that could be part of the problem. You can try hitting the nail set with the side of the hammer head---more difficult to slip off and hit fingers.

Are you driving the nail almost flush with just the hammer and then using the nail set to drive the head below the wood surface? If you are hitting your fingers you can hold the nail with needle nose pliers or a piece of cardboard with a slit in it.

I've had this problem before, and recently I made two oak window casings. I was using small brads to attach some of the molding. I also got a set of nail sets from HD: mine have indentations at the tip, rather than points. They do a pretty good job of holding the nail while you're hammering it in. Granted, they make a slightly larger hole in the wood, but it's worth it to get that nail head recessed all the way. I don't recall if the set is made by Stanley or someone else. I still had some problems with these small brads; the real solution would be a nail gun that could handle small nails.

Old dry studs are really hard, sometimes too hard to hammer a nail or screw a drywall screw without a pilot hole. If you are not using an air nailer, I recommend one. You can adjust the depth to get it just right. If the air nailer will not set the nails all the way even at it's deepest setting, or some of the nails get bent over, you are using too long of nails. For 3/4" trim with 1/2" drywall, use 2" nails if the studs are old and hard, but use 2 1/2" nails if the studs are new and still soft.

If you are not going to use an air nailer, try drilling pilot holes 80-90% of the fastener length and then hammering the nails in. Pilot holes are not just for screws.

You only use a punch for the last 1/8 inch or so of driving the nail.

Just use the hammer till it is barely above the surface.

It is getting harder and harder to find even a decent hammer anywhere (and a decent one is not $5).

The face should be barely crowned.

It is probably worth it to buy a 2x4 and practice.

Your hand has to be at the correct height above the surface to drive a nail straight.
Once you can get them almost flush, finishing up with a nail set will not be as hard.

Thanks for all the tips. I really should use the needlenose to save my fingers. I've used that before when driving small nails or tacks and it's great. I wish I had an air nailer. Brickeyee, you're right I could use practice. I don't do this often.

Another method is to place the nail set on its side, then position it on the nail head. then, just hit the flatside of the set. this will drive the nail flush with the wood. Then, use the set with the pointed end on the nailhead to drive it a bit further. Most of the time , I find that the so called indent on the nail is not very good.

I hold the nailset with my left hand with my...let's see....index, middle, and ring finger LIGHTLY, and my pinky rests very lightly at the intersection of the nailpunch and the head of the nail to steady and hold it on point. Then I whack it with the hammer.

It does take some practice.

The real problem is MANUFACTURING!!! Finish nails are SUPPOSED to provide a finished look by creating a SMALL hole, but several decades ago, I noticed manufactures do NOT put a dip in their nails heads anymore. I just nailed up casing, and MOST of the nails actually have a RAISED edge that creates a perfect condition for the nail set to slip off. In prior years, nail sets NEVER slipped.

Digging up 11 year old threads for random rants?

Why not? The problem is still relevant, and the manufactures are still producing a bad product. It isn't the fault of the operator but rather the company. Consumers should have a choice whether to purchase quality finish nails or an air hammer. I hope the change in nail design was not to force consumers into buying air nailers.

So buy from quality manufacturers for example https://www.mazenails.com/nails/HT* and don't worry about what they sell at the big box stores.

Thanks for the recommendation...the big box stores take another dive in selling a quality product! Looking back, I think I noticed the finish nail problem several decades ago when the big box stores came out, and I started buying from them. THANKS!!