They'll cry for their mama when they get thrown in jail for disobeying a judge's order. Too bad, so sad. Throw the book at them. Give them the max. Scare them straight. Cut the electricity and water and don't let any food in. Without their Starbucks and no potty, they'll be out within an hour.
Who's going to enforce THAT order? Seems to me, no order, no "closed for business" rule, counts, in Madison, Wisconsin.
On the other hand, if the judge's orders do work, then I suggest an aggressive proactive stance, and litigate EVERYTHING. Sue the absent DEM senators, sue the trespassers (at least for cleanup and security costs), etc.