Each on-track roadway maintenance machine and hi-rail vehicle shall have on board a flagging kit that complies with the operating rules of the railroad if:

(a) The equipment is operated over trackage subject to a railroad operating rule requiring flagging; and

(b)(1) The equipment is not part of a roadway work group; or

(2) The equipment is the lead or trailing piece of equipment in a roadway work group operating under the same occupancy authority.