This session presents a framework for the lifelong, sequential management of osteoporosis, organized around two recurring clinical decisions: when to interrupt therapy and how to move a patient from one agent to the next. It begins from the premise that no drug cures osteoporosis, that the skeletal benefit of every therapy dissipates once treatment stops, and that optimal management is individualized and built from the sequential use of antiremodeling and osteoanabolic agents. The session establishes that a drug holiday applies only to bisphosphonate therapy and argues for restricting the term to the bisphosphonate holiday. It reviews the evidence that bone mineral density gain and fracture risk reduction plateau after three to five years of bisphosphonate therapy, that protection wanes slowly after discontinuation, and that the risk of atypical femoral fracture rises with continued use and falls when therapy is stopped, and it operationalizes the holiday through reassessment of fracture risk at three to five years, with continuation, holiday, or a switch to another agent determined by whether the patient still meets treatment criteria. Turning to transitions, the session shows why step therapy, the fail first approach, does not work in osteoporosis, because the response to the more potent agents is blunted when they follow a bisphosphonate, and it aligns the initial choice of therapy with current fracture risk. It works through the major transitions in turn, bisphosphonate to denosumab or to an osteoanabolic agent, the long term use and the managed discontinuation of denosumab including the rebound in bone turnover and the ECTS protocol, the short course of estrogen that must be followed by a bisphosphonate, and the osteoanabolic to antiremodeling sequence that is required to preserve anabolic gains. It examines the rationale for using an osteoanabolic agent first, the limited settings in which an anabolic to anabolic or a denosumab to anabolic transition is effective, and the question of whether a shorter course of an anabolic drug can substitute for the full course. The session closes with long term maintenance therapy, the use of intermittent alendronate or infrequent zoledronate to preserve skeletal benefit indefinitely, and the principle that the clinician treats the patient rather than the disease.