This chapter critically evaluates the effectiveness of personalized assessment strategies in enhancing student learning outcomes, engagement, and self-regulated learning by synthesizing evidence on how tailoring assessments—through formative feedback, adaptive technologies, and learning analytics—impacts educational efficacy. Key insights derived from a comprehensive review of pertinent literature indicate that well-designed personalized assessments can significantly improve academic achievement and learner motivation, especially when providing immediate, actionable feedback and dynamically adapting to student progress. The effective integration of learning analytics for diagnosing needs and adjusting pathways further augments this potential. However, the overall success of personalized assessments is often contingent upon the quality of assessment design, the clarity of learning objectives, the pedagogical framework, and supportive conditions for both learners and educators. The principal conclusion is that while personalized assessment presents a powerful approach for optimizing individual learning trajectories and fostering deeper understanding, its benefits are best realized through careful, context-sensitive implementation and continuous empirical evaluation, with ongoing research needed to address scalability and ensure equitable access across diverse populations.