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Melanoma of the conjunctiva may occasionally involve the lacrimal drainage apparatus (LDA). This makes clinical management difficult. The authors describe 5 cases of conjunctival melanoma with LDA disease and make recommendations about its management.Retrospective review of case notes and histopathology reports.Five cases of LDA melanoma arising in patients with conjunctival melanoma are described. All 5 had orbital exenteration as part of their treatment. Melanoma of the LDA was clinically present at the time of exenteration in 1 case, found unexpectedly in 2 cases, and developed subsequent to exenteration in 2 cases. One patient died within 8 months of exenteration from metastatic melanoma. Two patients were disease free 3 and 5 years after exenteration. One patient developed metastasis in the parotid gland 4 years after exenteration but remained disease free 7 years after exenteration. One more patient has had a local recurrence in the maxilla and lateral nasal wall 4 years after exenteration, and after resection of that lesion and radiotherapy is disease free after 18 months. Seventeen patients underwent orbital exenteration for conjunctival melanoma over the period 1996–2013 at the authors’institution, with 5 having or developing LDA disease (29%). In the same period, there were 52 patients with conjunctival melanoma overall, with LDA involvement occurring in 5 of 52 patients (9.6%).Melanoma of the LDA may complicate conjunctival melanoma in a significant percentage of cases having orbital exenteration. The surgical technique for orbital exenteration in patients with conjunctival melanoma should take this into account by intentionally removing the lacrimal sac and upper nasolacrimal duct as well as the lacrimal canaliculi. If melanoma is found in the LDA, consideration should be given to wider en bloc excision of the LDA.