Red Dead Redemption 2

In free roam you occasionally will see a message pop up on screen letting you know that a rival posse has stolen a wagon/money bags a prison coach or something of the sort. When you see this message go and intercept said scenario, kill the rival members if you need to and most importantly steal the money bags or wagon and deliver them to the location on your map or destroy the wagon if that is what it tells you to do. Once the mission is complete all members of the posse will unlock the achievement.

If you so wish you can boost this with ONE other player. Have both players form a posse and have turns starting a free roam mission whereby you intercept a wagon and steal the money bags/wagon or any mission that offers kidnaps, mail bags, Wagon recovery or horse thefts. To do this have one person start the mission and go collect what they are told to and then simply have the person going for the achievement waiting nearby or following behind and have them swoop in and intercept the mission, it will get them to either destroy the wagon or deliver it; Note only do this after the message pops up saying "you can rival a posses mission" and pops up on the other players screen saying"A Rival posse can steal the wagon/horse etc"

The mission just east of Armadillo at MACFARLANE`S RANCH with Bonnie is ideal to boost this, or any mission that offers kidnaps, mail bags, Wagon recovery or horse thefts.

PLEASE NOTE: The mission with the canoes does not work for this achievement nor do the hunting missions.

Alternatively you can attain this achievement if you are targeted as an assassination and you escape, Thank you to Yurgi Windu in the comments for that information.

Thank you

For anyone who plays solo or does not feel like boosting, I have some tips! Though it will still involve a bit of luck.

-Make sure you have Dynamite or Fire Bottles in your inventory!

-I played a lot in Free Roam around Scarlet Meadows (the area around Rhodes). Note that there is a Free Roam mission the requires the player to bring 1 or 2 wagons to the mansion at Braithwaite Manor. The luck involves another player doing this mission while you are in the area!

-If you see a blue dot (another online player) traveling on a wagon (with possibly another behind them) on a road leading to Braithwaite Manor then odds are they are doing this mission.

-Follow behind them until they reach the long straight road south to the mansion. When they reach that road it should say "Attack another Player's Free Roam Mission"

-At this point, don't bother shooting the player or horses. Just equip your dynamite or fire bottles and toss 2-3 at one of the wagons. As long as you destroy at least one of the wagons the achievement should unlock (even if the player delivers the other one)!

The dynamite method should work for any delivery mission but I found that the delivery mission by Braithwaite Manor seemed to be most striaghtforward (literally) for others still struggling with this achievement.

There is some good hunting (boars, deer, coyotes) and easy access to shops in Rhodes if you set up camp in Scarlet Meadows and are waiting around trying your luck out at this. Best of luck!