Resource optimization and scheduling is a costly, challenging problem that affects almost every aspect of our lives. One example that affects each of us is health care: Poor systems design and scheduling of resources can lead to higher rates of patient noncompliance and burnout of health care providers, as highlighted by the Institute of Medicine (Brandenburg et al. 2015). In aerospace manufacturing, every minute re-scheduling in response to dynamic disruptions in the build process of a Boeing 747 can cost up to $100.000. The military is also highly invested in the effective use of resources. In missile defense, for example, operators must =solve a challenging weapon-to-target problem, balancing the cost of expendable, defensive weapons while hedging against uncertainty in adversaries’ tactics. Researchers in artificial intelligence (AI) planning and scheduling strive to develop algorithms to improve resource allocation. However, there are two primary challenges. First, optimal task allocation and sequencing with upper and lower-bound temporal constraints (i.e., deadlines and wait constraints) is NP-Hard (Bertsimas and Weismantel 2005). Approximation techniques for scheduling exist and typically rely on the algorithm designer crafting heuristics based on domain expertise to decompose or structure the scheduling problem and prioritize the manner in which resources are allocated and tasks are sequenced (Tang and Parker 2005; Jones, Dias, and Stentz 2011). The second problem is this aforementioned reliance on crafting clever heuristics based on domain knowledge. Manually capturing domain knowledge within a scheduling algorithm remains a challenging process and leaves much to be desired (Ryan et al. 2013). The aim of my thesis is to develop an autonomous system that 1) learns the heuristics and implicit rules-of-thumb developed by domain experts from years of experience, 2) embeds and leverages this knowledge within a scalable resource optimization framework, and 3) provides decision support in a way that engages users and benefits them in their decision-making process. By intelligently leveraging the ability of humans to learn heuristics and the speed of modern computation, we can improve the ability to coordinate resources in these time and safety-critical domains.