Abstract: Techniques for detecting malicious content using simulated user interactions are described herein. In one embodiment, a monitoring module monitors activities of a malicious content suspect executed within a sandboxed operating environment. In response to detection of a predetermined event triggered by the malicious content suspect requesting a user action on a graphical user interface (GUI) presented by the malicious content suspect, simulating, a user interaction module simulates a user interaction with the GUI without user intervention. An analysis module analyzes activities of the malicious content suspect in response to the simulated user interaction to determine whether the malicious content suspect should be declared as malicious.