Traditional and emerging forms of assessment for measuring technology readiness are presented in the context of society´s need for assessing twenty-first century skills. Workforce preparation is identified as a driving force for new forms of assessment, while rapid advances in information technologies offer opportunities for new techniques to emerge. Recent approaches to learning, such as digital game environments, demonstrate that alternative forms of assessment are emerging to fulfill these changing needs. In this chapter the need for technology readiness is introduced in the context of assessing twenty-first century skills. Conceptual and practical considerations are addressed within the categories of foundation skills, technology applications, attitudes toward technology, communicating with technology and digital citizenship. A presentation of emerging assessment techniques leads to discussion of the importance of technology readiness for preparing a productive workforce. In addition, this chapter includes prospects for forms of assessment unique to new digital media.