Computer networks have become a critical infrastructure. It is hence increasingly important to guarantee a correct, consistent, and secure network operation at any time, even during route updates. However, most existing works on consistent network update protocols focus on connectivity properties only (e.g., loop-freedom) while ignoring basic (security) policies. This paper studies how to update routes in a software-defined network in a transiently policy-compliant manner. In particular, our goal is to enforce waypoints: at no point in time should it be possible for packets to bypass security critical network functions (such as a firewall). This problem is timely, given the advent of network function virtualization which envisions more flexible middlebox deployments, not limited to the network edge. This paper shows that enforcing waypoint traversal in transient states can be challenging: waypoint enforcement can conflict with loop-freedom. Even worse, we rigorously prove that deciding whether a waypoint enforcing, loop-free network update schedule exists is NP-hard. These results hold for both kinds of loop-freedom used in the literature: strong and relaxed loop-freedom. This paper also presents optimized, exact mixed integer programs to decide feasibility quickly and to compute optimal update schedules. We report on extensive simulation results, and also study scenarios where entire “service chains,” connecting multiple waypoints, need to be updated consistently.