A work vehicle multi-coupler assembly having a controlled breakaway feature include a pair of coupling elements that mate along a coupling axis. A shear pin is carried by one of the coupling elements. A coupler mechanism connected to the second coupling element and configured to engage the shear pin to bring the first coupling element into mating engagement with the second coupling element. The coupler mechanism is configured to shear the shear pin to permit movement of the first coupling element away from the second coupling element along the coupling axis during a breakaway event.