Westerado: Double Barreled

Westerado: Double Barreled

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Wallowing in Failure Achievement
I've followed pretty much every guide on how to get this achievement, to no avail.
At the point the sheriff should be depressed, he just tells me to go get 5 wanted men.
I took him on all escort missions and failed them all.
What the hell am I doing wrong?
Last edited by Superkumi; Aug 13 @ 7:09am