Software-defined Networking (SDN) enables flexible network management, but as networks evolve to a large number of end-points with diverse network policies, higher speed, and higher utilization, abstraction of networks by SDN makes monitoring and debugging network problems increasingly harder and challenging. While some problems impact packet processing in the data plane (e.g., congestion), some cause policy deployment failures (e.g., hardware bugs); both create inconsistency between operator intent and actual network behavior. Existing debugging tools are not sufficient to accurately detect, localize, and understand the root cause of problems observed in a large-scale networks; either they lack in-network resources (compute, memory, or/and network bandwidth) or take long time for debugging network problems. This thesis presents three debugging tools: PathDump, SwitchPointer, and Scout, and a technique for tracing packet trajectories called CherryPick. We call for a different approach to network monitoring and debugging: in contrast to implementing debugging functionality entirely in-network, we should carefully partition the debugging tasks between end-hosts and network elements. Towards this direction, we present CherryPick, PathDump, and SwitchPointer. The core of CherryPick is to cherry-pick the links that are key to representing an end-to-end path of a packet, and to embed picked linkIDs into its header on its way to destination. PathDump is an end-host based network debugger based on tracing packet trajectories, and exploits resources at the end-hosts to implement various monitoring and debugging functionalities. PathDump currently runs over a real network comprising only of commodity hardware, and yet, can support surprisingly a large class of network debugging problems with minimal in-network functionality. The key contributions of SwitchPointer is to efficiently provide network visibility to end-host based network debuggers like PathDump by using switch memory as a "directory service" - each switch, rather than storing telemetry data necessary for debugging functionalities, stores pointers to end hosts where relevant telemetry data is stored. The key design choice of thinking about memory as a directory service allows to solve performance problems that were hard or infeasible with existing designs. Finally, we present and solve a network policy fault localization problem that arises in operating policy management frameworks for a production network. We develop Scout, a fully-automated system that localizes faults in a large scale policy deployment and further pin-points the physical-level failures which are most likely cause for observed faults.