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Hello if someone could help me with this it would be much appreciated. For some reason even though I completed the bandit camp event (discouraged Logan to go) as well as having bareshades expansion event completed and the bandits moral at 100. As well I have the completed the Country Road event/ Ste's new road. I never get the option in the tavern "Check what the thug is up to". So I can never get the clash with barrel and then never get the event with normal Logan. Does anyone know what I am missing? 

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Go to the camp and raise the morale above 28 (You can give money to Jasper and be a bitch of thugs) then go to the bar enter and leave the place that unleashes a clash with Barrel, you will see a dialogue with Logan, then go to sleep (rest 8 hs) in Barashade's house the last event appears with Logan to get his 2 heart (Save your game, you have two options, lose him or be his friend)

Check what the thug is up too isn't what triggers the clash dude. It's random when you enter the bar. However Oldnigth is also right that if you wanna see the "check what the thug is up" event you do need bandit morale to be above 28.