Background: Popliteal cysts are common and present as asymptomatic lumps in the medial popliteal fossa. Some have complex internal characteristics such as septa and loose-bodies. However, not all are popliteal cysts and can be aggressive. These lesions need to be differentiated by the absence of the communicating neck with the joint on ultrasound. Presence of Doppler flow of non-communicating cysts requires further evaluation on MRI, prior to performing a biopsy. Using a case series, we propose an algorithmic approach that is simple and will help identify the malignant lesions and institute appropriate management. Case-Presentation: Popliteal Cyst: On ultrasound: characteristic neck communicating with knee joint. Synovial Sarcoma: Gadolinium enhancement, with areas of low-, iso- and hyper-intense signal to fat on T2. Synovial-Osteochondromatosis: Non-mineralized: T1-low/intermediate intensity; T2-high intensity. Mineralized type: low intensity on T1 & T2. Thrombosed Popliteal Aneurysm: Lamellated appearance-high/low signal intensity on T2. Myxoid-Liposarcomas: Inhomogeneous appearance; homogenous with gadolinium. Usually require a biopsy for diagnosis. Conclusion: The cystic lesions in the medial aspect of the popliteal fossa can be misdiagnosed. Our article reiterates the importance of the communicating neck that separates popliteal cysts from other mimics. We have proposed an algorithm to identify these mimics.