Recent advancements in computational capabilities in both hardware and software have encouraged scholars who study the past to apply modeling and simulation approaches that are more generally used for studying modern social systems. Although applying such popular approaches as agent-based modeling can be applicable, modelers and domain researchers do need to heed drawbacks that are often present for many studies addressing ancient social questions. This talk will look at several modeling and simulation examples as conducted by the speaker and present different issues that appear particularly in efforts looking at questions in past social systems. Discussion will focus on modeling techniques that can be adapted and used for answering research questions as well as evaluate the utility of outputs produced. Modeling approaches discussed focus on socio-ecological complex systems, with examples drawn from agricultural and transportation systems.