Free tissue transfer is widely used for the reconstruction of complex tissue defects. The survival of free flaps depends on the patency and integrity of the microvascular anastomosis. Accordingly, the early detection of vascular comprise and prompt intervention are indispensable to increase flap survival rates. Such monitoring strategies are commonly integrated into the perioperative algorithm, with clinical examination still being considered the gold standard for routine free flap monitoring. Despite its widespread acceptance as state of the art, the clinical examination also has its pitfalls, such as the limited applicability in buried flaps and the risk of poor interrater agreement due to inconsistent flap (failure) appearances. To compensate for these shortcomings, a plethora of alternative monitoring tools have been proposed in recent years, each of them with inherent strengths and limitations. Given the ongoing demographic change, the number of older patients requiring free flap reconstruction, e.g., after cancer resection, is rising. Yet, age-related morphologic changes may complicate the free flap evaluation in elderly patients and delay the prompt detection of clinical signs of flap compromise. In this review, we provide an overview of currently available and employed methods for free flap monitoring, with a special focus on elderly patients and how senescence may impact standard free flap monitoring strategies.