Objectives: The surgical management of tumors involving the hypoglossal canal presents unique challenges. Traditional skull base approaches provide only limited access to this region. Additionally, because the hypoglossal canal lies medial and anterior to the jugular foramen, preservation of surrounding neurovascular structures, such as the sigmoid sinus and jugular foramen nerves, is potentially possible. We sought to illustrate our decision-making strategy when faced with a tumor involving the hypoglossal canal.Methods: Our case series of 3 patients describe the different forms of hypoglossal canal involvement (extra-dural, intra-dural, and trans-dural). Tumor pathologies included a hypoglossal nerve schwannoma, a meningioma, and a paraganglioma.Results: We use 3 main surgical approaches to the hypoglossal canal. Extra-dural tumors are accessed via a unique, modified infratemporal fossa procedure. The jugular vein, carotid artery, and cranial nerves IX, X, and XI are followed up to the skull base. The facial nerve is skeletonized but not re-routed; the jugular bulb is identified but not resected. Cranial nerve XII is microdissected free from the jugular foramen and traced to the hypoglossal canal. Intra-dural tumors are managed using a far-lateral craniotomy. Removal of the jugular tubercule provides circumferential visualization of the hypoglossal canal. Combining the 2 approaches permits resection of dumbbell-shaped trans-dural tumors. Larger trans-dural tumors require a transjugular craniotomy.Conclusion: The intra- and extra-dural involvement of the hypoglossal canal defines our decision-making strategy when choosing a surgical approach to this region. Preservation of surrounding neurovascular structures should be considered for smaller tumors.