3 pins that are not longer usable.  I have the starter/holder punch and the Grace roll pin punches.  I am also using the Wheeler AR vise that holds the bolt on the side.  What am I doing wrong?  Is there a trick to getting these things in.  I've built a couple of lowers with no trouble, but these little ejector pins are driving me crazy.  Off to order more roll pins.

have the extractor in place-drop the spring and ejectorin the hole and lever it down with a piece of fired brass. run a slave pin through the bolt assy and carefully install the spring pin.chances are you are hitting the full round area of the ejector.   good luck!!!

If the ejector is not in far enough or not oriented correctly then the retaining pin is not going in.

Thanks for the replies so far.  I have used a spare punch to make sure the ejector was not blocking the hole.  

Looking at the bolt, it appears one of the holes for the pin is larger than the other.  Does it matter which hole I try to put the pin in from?

AFAIK the holes should be the same.
You may have some material peened into the small hole.

Probably, as said, the roll pin hitting the ejector.  I had the same problem with the first tool I bought, I ended up with the Young tool, no more problems.

Try a small nail as a locator pin, that may help.  I find the vibration of tapping in the roll pin makes the ejector rotate.

Some bolts do have different size holes.  The pin can only go into and come out of one hole.  If you don't mind me asking, who makes your bolt?

Also, there are different length ejector pins in the market.

HighSpeedSteel

Will the pin go in  smoothly without the ejector/spring being in the bolt?  In other words, with no ejector to interfere the pins should go in with no problem, if it doesn't, you many have damaged surfaces in/around the pin holes or incorrect pin diameter or incorrect pin hole diameter.  Make sure the pin will fit the bolt first.

Next, will the pin smoothly fit the ejector with the ejector out of the bolt (same type of check of pin/hole size and condition as with the bolt).

If the pin will fit the holes in the ejector and bolt separately then the issue is alignment of the holes when installing the pin.  

I seldom remove my ejector(s), but when I do I've never had an issue reinstalling them.  A light tap on the pin with a tack hammer (my gunsmithing hammer) drives the pin(s) in.

It is an ARP Superbolt for my 6.8.  I haven't tried putting a pin in without the ejector in place.  Once I have a new pin, I will try that..

The ejector was stuck in the flush position against the bolt face.  I figured maybe the spring was broken or it was clogged as I had been shooting my new suppressor.  When I got the ejector out, it was just clogged with carbon and what appeared to by tiny brass flakes.  I was able to run a 1/16" punch through the hole with the spring and ejector in place though.

If is don't fit don't force it.

The pin should just drop right in as long as the extractor is oriented correctly.  Just compress the ejector with a spent brass and it should just go right in.

Couple of thoughts...

First, I always cut a bevel of one end of the roll pin to make it easier to insert. Just use a sheet of sandpaper and rub the end of the roll pin at a 30-45 degree angle.

MAKE SURE you are using quality roll pins. All roll pins are not created equal. The roll pins that hardware stores sell are usually off shore crap that are sometimes out of spec. I had the SAME problem using hardware store roll pins.

The best pins (and easiest to install) are spiral coil pins.

Is your bolt coated with something by chance?

The ARP Superbolt has on one side a slightly larger hole for the pin punch that is slightly larger than the roll pin.    If you look closely under magnification this will be more clear.  
To help with driving the roll pin in you should use the next larger size roll pin punch.   If the roll pin punch is too small you may begin to flair the end of the roll pin you are trying to drive in.    With a normal bolt you will need to use the 1/16 roll pin to finish flush however with the Superbolt you can get it seated normally with the larger size pin punch.   Of course as others mentioned the roll pin needs to be the correct size too and the ejector itself is not blocking the pin.

Bama,

Thank you.  That is very helpful.  I do see that one side of the hole is slightly larger than the other.  I was getting flaring from using the 1/16 roll pin punch.  I will try the next size up when my new pins arrive.