In health professions education, tightly sequenced curricula may offer few opportunities to repeat or remediate single courses. Failure can prevent progression and require repetition of a semester or academic year, with serious financial and personal consequences. A structured reassessment can provide a compassionate alternative without lowering standards. One rigorous opportunity to revisit weak content and demonstrate mastery produces new evidence of competence while preserving academic integrity. It can support a student at risk of failure while providing an equitable, earned pathway for any learner seeking a higher grade. This practice began as an individual response to a student at risk of failing pharmacology, the only course preventing progression. Rather than alter the grade without new evidence of learning, I offered a cumulative reassessment with a minimum passing threshold established with the program director. The student’s performance exceeded my expectations and challenged my resistance to additional assessment opportunities. I had viewed the final course grade as fixed and worried that reassessment might weaken standards or reduce accountability. Instead, I began to question whether rigor requires preserving an initial result when a learner can later demonstrate mastery. Over time, this second-chance approach evolved from a discretionary remediation option into a syllabus-based opportunity for all students. Each learner may reassess content associated with their lowest nonfinal examination score, ensuring improvement is earned through renewed study. Drawing on learner experiences, this reflection examines how a reluctant exception evolved into a universal policy and reshaped my understanding of rigor, fairness, and remediation. It considers whether second chances weaken standards or allow educators to base progression decisions on the strongest valid evidence of learning, and if assessment design already provides sufficient opportunities for recovery.