I've got a couple of 38-55 single shots. A rolling block and a Uberti High Wall. What I found from the two rifles and from reading around is that there seems to be a lot of variation in bore and groove sizes on 38-55 barrels. Mostly the single shot guns are around .376 while the later lever rifles are up around .379 to .380. This seems to be due to the early Ballard cartridge size vs the later Winchester 38-55.
What it means is that you'll want to get a soft lead round ball and pound it down into the bore than carefully push it back out and measure the groove and bore from the impressions of the swaged plug. And obviously (I hope

), you realize that you want to use a plastic mallet to beat the lead ball into the muzzle.
What I found from my own testing is that my old rolling block with the Shiloh barrel refit needs a .377. Meanwhile my Uberti needs the more "lever gun" .380 size.
I started with the basic Lee dies. But due to the variation I found in all this I ended up making a couple or three different mouth sizing and flaring inserts to suit the diameters of the bullets needed for each rifle. Luckily I've got a machine shop so I can do this for myself.
If you don't have this option the nearest you can do is to not full length size the brass. Luckily the casings are slightly tapered so it's pretty easy to partially size down the brass then lightly flare the mouth to get a reasonable fit and neck tension on the reloads.
As for Trail Boss in rifle cartridges I tend to not like it. Look at the muzzle velocity and peak pressure. For handgun cartridges TB works like a charm and has low peak pressures. But when we start using it in big capacity rifle cartridges the pressure can jump up to values far higher than other powders produce for the same muzzle velocity. And that's simply extra abuse for the brass and the gun itself. So I tend to prefer powders that are lower in pressure for the velocity they produce. And after that I try to find one that provides a good fill for the brass so hopefully the pressures are more consistent.
My current best load for my High Wall, which I've been shooting the most for the past couple of years, is a Bullet Barn 255gn bullet bumped up to .382" (courtesy of that machine shop used to make my bumping die) pushed by 29gns of IMR4895. Muzzle velocity in my case is roughly 1380fps. And I need to get back to my testing as the rifle seems to want to make tighter groups with a slightly lower muzzle velocity.
Don't think that the .38-55 can't reach out either. After the match at Heffley this year was done for the day a bunch of us went out and plinked the long distance gongs for a while. For giggles I sighted in for and hit the furthest out gong up the hill. Now this is a roughly 6 ft saw blade. But it's out at 600'ish yards and looked pretty darn small in the peep sights. I hit it on my first try (very lucky guess on the elevation setting) and then missed due to wind. Then I "Kentucky'd" some hold to the side for the wind and got a second hit. I was feeling quite smug at that point and then someone laughed and said to do it again but free standing. I laughed. But figured "why not?"..... I sent off the shot and waited.... and waited.... I figured I missed and just then we all heard the distant "ting" com back at us. About a good 3 seconds all told from shot to "ting"..... I put the rifle away at that point. Nothing like a perfect sized single shot group....
