Systems and methods for dynamically providing video checkpoint questions to counter viewer distraction events are disclosed. In embodiments, a method includes: initiating, by a computing device, a viewing session of a video module at a user computer system; determining, by the computing device, a distraction event with respect to a viewer of the video module during the viewing session, wherein the distraction event is associated with content at a distraction point in the video module; dynamically generating, by the computing device, a checkpoint question for the viewer based on the content at the distraction point in the video module and in response to the determining the distraction event; and presenting, by the computing device, the checkpoint question to the viewer during the viewing session.