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Pyoderma gangrenosum (PG) is a rare, non-infective ulcerating skin disorder commonly associated with systemic inflammatory or haematological conditions. This report highlights two postpartum cases of PG, both presenting with severe ulcerations near caesarean section (C-section) scars. In both cases, the initial consultation with the surgical team resulted in plans for surgical debridement, which were made prior to dermatology review. These plans were subsequently cancelled and, in retrospect, given the underlying diagnosis of PG, would likely have been detrimental to patient outcomes. Rapid diagnosis and appropriate treatment with corticosteroids led to favourable outcomes. These cases emphasise the importance of considering PG in differential diagnoses of non-healing postoperative wounds, particularly in the postpartum period.