From the Dev log:
Event: ‘I owe you a beer’ - entering your new home (Req: Evening, Bareshade's Expansion event completed, Ste’s New Farm Road completed, ‘Clash with Barrel’ seen, ‘Ask about his work’ done with helping, Like 40, Love 1)
So if you mean do you got to have the Defense part of the expansion done then yeah.
If you mean the defense you built with Logan just after the bandit attack, that didn't stop me from getting the clash.
Have you checked your Bandit's Camp morale? I think I have noticed Barrel doesn't come to the pub when the Camp morale is very low (the "Check what the thug is up to" choice is not on the Bar menu if I am recalling correctly). That might be the problem, Barrel is the "thug", if he is not there there can be no clash. Just what I am remembering, I can't swear to it.