This paper introduces a potential learning scheme that can dynamically predict the stability of the reconnection of subnetworks to a main grid. As the future electrical power systems tend toward smarter and greener technology, the deployment of self sufficient networks, or microgrids, becomes more likely. Microgrids may operate on their own or synchronized with the main grid, thus control methods need to take into account islanding and reconnecting of said networks. The ability to optimally and safely reconnect a portion of the grid is not well understood and, as of now, limited to raw synchronization between interconnection points. A support vector machine (SVM) leveraging real-time data from phasor measurement units is proposed to predict in real time whether the reconnection of a subnetwork to the main grid would lead to stability or instability. A dynamics simulator fed with preacquired system parameters is used to create training data for the SVM in various operating states. The classifier was tested on a variety of cases and operating points to ensure diversity. Accuracies of approximately 85% were observed throughout most conditions when making dynamic predictions of a given network.