Cavernous sinus meningioma (CSM) with orbital involvement presents a unique challenge to modern-day neurosurgeons. In the modern era of preventive medicine with enhanced screening tools, physicians encounter CSM more frequently. An indolent natural history, late clinical presentation, close proximity to vital neurovascular structures, poor tumor-to-normal tissue interface, and high risk of iatrogenic morbidity and mortality with aggressive resection add to the complexity of decision-making and optimal management of these lesions. The clinical dilemma of deciding whether to observe or intervene first for asymptomatic lesions remains an enigma in current practice. The concepts of management for CSM with orbital involvement have gradually evolved from radical resection to a more conservative surgical approach with maximal safe resection, with the specific goals of preserving function and reducing proptosis. This change in surgical attitude has enabled better long-term functional outcomes with conservative approaches as compared with functionally disabled outcomes resulting from the pursuit of anatomical cure from disease with radical resection. The advent of stereotactic radiosurgery as an adjunct tool to treat residual CSM has greatly shaped our resection principles and planning. Interdisciplinary collaboration for multimodality management is key to successful management of these difficult to treat lesions and tailor management as per individual's requirement.