Despite the emerging importance of flexible project management approaches, such as agile extreme and hybrid methodologies, the algorithmic support of these approaches is still insufficient. In addition, single project scheduling has received far more attention than have schedules of multilevel projects, such as project portfolios or multi projects. This lack of scheduling techniques is especially true for flexible portfolios, such as agile, hybrid, and extreme project portfolios. While multilevel project scheduling algorithms already exist for fixed multilevel project structures, they are not able to handle flexible structures. This chapter proposes algorithms to schedule both flexible single and multilevel projects. The proposed algorithms handle both flexible and unplanned tasks and dependencies. They handle both single and multimode completion modes, and both renewable and nonrenewable resources. In addition, this chapter proposes a matrix-based risk-valuation framework to evaluate risk effects for flexible projects and portfolios. With this framework, project scheduling approaches are compared.