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Transdural growth of head and neck malignancies has a major impact on treatment planning and patient prognosis. Whereas tumors remaining extradural can be excised through a facial approach, tumors that transgress the dura require a combined craniofacial surgery, including dural resection, to obtain free surgical margins and often major reconstructive efforts to avoid postsurgical complications. Several studies have demonstrated the negative impact of dural invasion in patient outcome, together with the presence of positive margins and tumor histology. Therefore, efforts should be made to recognize this feature preoperatively. Magnetic resonance has proven to be the most accurate image modality to depict dural invasion and perineural spread of tumors. Dural enhancement, although very sensitive for dural invasion, has a low specificity as it may also result from venous congestion and reactive fibrovascular changes. This report will review the predictive value of MRI in the depiction of dural invasion and present a retrospective study assessing the predictive value of MRI for dural invasion by head and neck tumors performed at our institution.