Systems, methods, and computer-readable media are used to determine whether specific electronic pen gestures with respect to pen-based computing systems should be processed as "press-and-hold" gestures (e.g., to activate right mouse button click actions). Such methods may include: (a) measuring two different parameters associated with pen interaction or orientation with respect to a digitizer during a pen-down event; and (b) determining whether the pen-down event constitutes a press-and-hold gesture based, at least in part, on the measured parameters. In some instances, if the systems and methods cannot immediately determine whether a press-and-hold gesture is intended, measurements may be made again (as many times as necessary or until a time-out occurs) such that the determining step can be performed one or more additional times taking into consideration the additional parameter measurement data collected since the original parameter measurements. Additionally, standards for determining whether a dwell gesture constitutes a press-and-hold gesture may be set and/or adjusted, taking into consideration features associated with a specific user's use of the pen-based computing system (e.g., customization of standards based on model user input and/or a user's past performance of press-and-hold actions).