Cognitive assessment has become reliant on outdated analogue methods that are slow, resource-intense, highly inefficient, and expensive, and yield relatively coarse metrics of human cognition and behavior. The goals of this presentation are twofold. First, we will characterize the technology crisis unfolding in neuropsychology, which will entail a brief history on the evolution of the problem, as well as, the historical barriers and ongoing challenges to adoption of technology. Second, we will present a conceptual overview of our vision for digital phenotyping of human behavior in both research, clinical and community settings as technology evolves. We will focus specifically on remote assessments deployed in real-world settings outside the clinic, as well as, passive monitoring for high-frequency data capture. Throughout, we will address the proposed benefits of each approach individually, and highlight the utility of a multi-method approach.