abstract: The use of reactive security mechanisms in enterprise networks can, at times, provide an asymmetric advantage to the attacker. Similarly, the use of a proactive security mechanism like Moving Target Defense (MTD), if performed without analyzing the effects of security countermeasures, can lead to security policy and service level agreement violations. In this thesis, I explore the research questions 1) how to model attacker-defender interactions for multi-stage attacks? 2) how to efficiently deploy proactive (MTD) security countermeasures in a software-defined environment for single and multi-stage attacks? 3) how to verify the effects of security and management policies on the network and take corrective actions? I propose a Software-defined Situation-aware Cloud Security framework, that, 1) analyzes the attacker-defender interactions using an Software-defined Networking (SDN) based scalable attack graph. This research investigates Advanced Persistent Threat (APT) attacks using a scalable attack graph. The framework utilizes a parallel graph partitioning algorithm to generate an attack graph quickly and efficiently. 2) models single-stage and multi-stage attacks (APTs) using the game-theoretic model and provides SDN-based MTD countermeasures. I propose a Markov Game for modeling multi-stage attacks. 3) introduces a multi-stage policy conflict checking framework at the SDN network's application plane. I present INTPOL, a new intent-driven security policy enforcement solution. INTPOL provides a unified language and INTPOL grammar that abstracts the network administrator from the underlying network controller's lexical rules. INTPOL develops a bounded formal model for network service compliance checking, which significantly reduces the number of countermeasures that needs to be deployed. Once the application-layer policy conflicts are resolved, I utilize an Object-Oriented Policy Conflict checking (OOPC) framework that identifies and resolves rule-order dependencies and conflicts between security policies. / Dissertation/Thesis / Doctoral Dissertation Computer Science 2020