This paper presents a risk-based probabilistic small-disturbance security analysis (PSSA) methodology for use with power systems with uncertainties. This novel addition to existing dynamic security assessment (DSA) techniques can be used to quantify the small-disturbance stability risks associated with forecasted operating conditions. This approach first establishes the probability density functions (PDFs) for the damping of the critical oscillatory electromechanical modes by modeling the stochastic variation of system uncertainties, such as loading levels, intermittent generation sources, and power flows through voltage-source converter–high-voltage direct current (VSC–HVDC) lines. The produced PDFs are then combined with severity measures (either simple risk matrices or continuous functions) in order to quantify the risk of stability issues for the system associated with the forecasted operating scenario. In addition, the PSSA is used to establish risk-based operational limits and the concept of a probabilistic security margin is introduced to more accurately represent the probabilistic operation of uncertain power systems. The proposed techniques are demonstrated using a multiarea meshed power system incorporating two VSC-HVDC systems, one of which is connected to a large wind farm.