Capture the flag (CTF) exercises have been used in cybersecurity for fun and for training and education for many years. In our own experience, students often become frustrated when they do not make progress. This has also been reported by others. Even with instructor office hours and TA support, many students have trouble and struggle with completing hands-on exercises. Our goal is to provide tools to help students be more engaged by automatically detecting when they are struggling, and to potentially offer a hint when that happens.