This chapter highlights the current challenges and future directions in cartilage tissue engineering. First, the need for additional characterization studies of native cartilage tissues and the development of joint- or tissue-specific assays is discussed. The importance of engineering constructs that accurately reflect the structural and functional properties of native cartilages and developing strategies to compare engineered implants quantitatively to native tissues is highlighted. The chapter also discusses issues related to selecting appropriate assessments for preclinical evaluation and the many challenges of translating technologies from academic research to clinical application. Finally, the importance of adapting engineered tissues to withstand inflamed environments such as those within arthritic joints is highlighted. Overall, the goal of this chapter is to provide a high-level overview of the major barriers that currently hinder the clinical translation of tissue-engineered cartilages.