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This case series presents 18 patients with primary and secondary malignant lacrimal sac and nasolacrimal duct tumors and their pattern of tumor spread. Squamous cell carcinoma was the most common histology and, in 15/18 patients tumor involved both the lacrimal sac and duct at the time of diagnosis. In 11/16 patients on CT, the nasolacrimal bony canal was smoothly expanded without erosive changes. Tumor was not observed solely within the nasolacrimal duct in any patient. Only 1 patient presented with nodal metastasis and there was no intracranial tumor extension or perineural tumor spread. The authors conclude that malignant lacrimal sac and nasolacrimal duct tumors tend to expand the nasolacrimal bony canal, rather than erode it. CT was superior to MR imaging in characterizing expansion versus erosion of the nasolacrimal bony canal.