The association between chronic ulcers and squamous cell carcinomas (SCCs) is well established. Their clinical presentations, however, are varied, ranging from innocously appearing lesions to overtly exophytic growths. We present a series of cases with heterogeneous clinical presentations and different treatment outcomes. Case series - patient 1 was a 69-year-old man with an 18-month history of static non healing venous leg ulcer, but no sinister features, biopsy was performed to rule out Marjolin's transformation, histology revealed SCC and treatment was simple excision and skin grafting; patient 2 was a 73-year-old lady with an 18-month history of non healing ulcer (innocuous appearance) over distal interphalangeal joint of index finger, histology revealed SCC with deeper extension and treatment was amputation of distal half of finger; patient 3 was a 73-year-old lady with a 12-month history of non healing fungating leg ulcer with irregular borders and everted edges, histology revealed SCC (tumour eroding tibia and distant metastasis) and treatment was above-knee amputation, radiotherapy and palliation. Whilst SCC is amenable to simple excision in the early stages, delay in diagnosis could result in loss of the affected digit or limb; an SCC which has metastasised is also life threatening. Therefore, a low threshold to biopsy static non healing ulcers or ulcers in unusual sites should be adopted even in those not manifesting any evidence of malignancy.