The ability to detect and differentiate breakpoints during task execution is critical for enabling defer-to-breakpoint policies within interruption management. In this work, we examine the feasibility of building statistical models that can detect and differentiate three granularities (types) of perceptually meaningful breakpoints during task execution, without having to recognize the underlying tasks. We collected ecological samples of task execution data, and asked observers to review the interaction in the collected videos and identify any perceived breakpoints and their type. Statistical methods were applied to learn models that map features of the interaction to each type of breakpoint. Results showed that the models were able to detect and differentiate breakpoints with reasonably high accuracy across tasks. Among many uses, our resulting models can enable interruption management systems to better realize defer-to-breakpoint policies for interactive, free-form tasks.