The video is the only time I succeeded after almost 100 tries and I give up trying more times, lol, at least for now. So hard to trigger for me. If you don't have a lot of time and patience, I wouldn't recommend you to try this.

The Earliest point is just after "A Quiet Time" mission when Lenny is at camp. I finished the "Five Finger Fillet" Camp Companion Activity with him. Just wanted to keep my promise to test it for some of the comments' requests. For myself, I would definitely get the weapon even earlier with my Hosea's way.    • RDR2Earlist time to get a Rolling Bl...   because getting Lenny's Rolling Block is way harder than Hosea's.

There are 2 difficult parts:
1. Lenny's posture: Sitting on the Stool Reading the Newspaper in his Tent with the Rolling Block on His Back. Literally, at least 100 attempts and only saw it twice. If you see it, just try it. Other locations or postures even having the rifle with him, don't work.
2. The rarity of getting Lenny out using Companion Glitch: Companion Glitch is already a chance event itself. Whether it can be triggered or Whoever comes out is totally random. At the point of my game, you can Lure out Lenny, Kieran, Dutch, Bill, John and Karen. Lenny being the least likely to come out.

I want to try the earliest point since if you finish enough missions in chapter2, you will be finally at the Gun Store with John to get it. If you find some patterns to make it easier and more certain to happen , please let me know. Thank you for watching.