A breakaway fifth wheel coupling may couple a semi-tractor to a semi-trailer. In one embodiment, a breakaway fifth wheel coupling may include a top plate, a bottom brace, and a release mechanism that releasably attaches the top plate to the bottom brace. When a rollover event is detected, the release mechanism may allow the top plate to release from the bottom brace, thereby allowing the semi-tractor to separate from the semi-trailer. The fifth wheel coupling may include a pair of pivot rails that promote consistent decoupling of the top plate from the bottom brace. The breakaway fifth wheel coupling may reduce the likelihood of the semi-tractor participating in a rollover accident.