This chapter presents two case studies on hematopoietic stem cell transplantation (HSCT) in chronic lymphocytic leukemia (CLL). Two case studies present a series of questions and answers. The first case study commences with a discourse on whether appropriate to consider HSCT for the patient at 11 months time, and ends with question of whether the patient had Richter's transformation and also any role for HSCT. The second case study commences with a discourse on a role for early HSCT in CLL, and ends with a question of upper age limit for allogeneic HSCT in CLL patients.