Capstone projects usually represent the most significant academic endeavor with which students have been involved. Time management tends to be one of the hurdles. On top, University students are prone to procrastinatory behavior. Inexperience and procrastination team up for students failing to meet deadlines. Supervisors strive to help. Yet heavy workloads frequently prevent tutors from continuous involvement. This article looks into the extent to which conversational agents (a.k.a. chatbots) can tackle procrastination in single-student capstone projects. Specifically, chatbot enablers put in play include (1) alerts, (2) advice, (3) automatic rescheduling, (4) motivational messages, and (5) reference to previous capstone projects. Informed by Cognitive Behavioural Theory, these enablers are framed within the three phases involved in self-regulation misalignment: pre-actional, actional, and post-actional. To motivate this research, we first analyzed 77 capstone-project reports. We found that students’ Gantt charts (1) fail to acknowledge review meetings (70%) and milestones (100%) and (2) suffer deviations from the initial planned effort (16.28%). On these grounds, we develop GanttBot, a Telegram chatbot that is configured from the student’s Gantt diagram. GanttBot reminds students about close landmarks, it informs tutors when intervention might be required, and it learns from previous projects about common pitfalls, advising students accordingly. For evaluation purposes, course 17/18 acts as the control group (
) while course 18/19 acts as the treatment group (
students). Using “overdue days” as the proxy for procrastination, results indicate that course 17/18 accounted for an average of 19 days of delay (SD = 5), whereas these days go down to 10 for the intervention group in course 18/19 (SD = 4). GanttBot is available for public usage as a Telegram chatbot.