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Chatbots have recently been used as a persuasive technology to help support behavioral change, making them an intriguing design space for students' study habits and skills. This paper investigated the feasibility of using chatbots for promoting behavioral change of college students majoring in Computer Science (CS). We conducted semi-structured interviews with CS peer-tutors and surveyed university freshmen to understand students' study habits and identify technical intervention opportunities. Inspired by the findings, we designed StudyBuddy, a chatbot prototype deployed in Slack that periodically sends tips, provides assessments of students' study habits via surveys, helps the students break down assignments, recommends academic resources, and sends reminders. We evaluated the usability of the prototype in-depth with 8 students (both first-year and senior students) and 5 course instructors followed by a large scale evaluative survey (n=117) using video of the prototype. Our research identified important design challenges such as building trust and preserving privacy, limiting interaction costs, and supporting both immediate and long-term sustainable support. Likewise, we proposed design recommendations that demonstrate context awareness, personalize the experience based on user preferences, and adapt over time as students mature and grow.<\/jats:p>","DOI":"10.1145\/3449171","type":"journal-article","created":{"date-parts":[[2021,4,22]],"date-time":"2021-04-22T17:49:24Z","timestamp":1619113764000},"page":"1-32","update-policy":"https:\/\/doi.org\/10.1145\/crossmark-policy","source":"Crossref","is-referenced-by-count":37,"title":["Let's Talk It Out"],"prefix":"10.1145","volume":"5","author":[{"given":"Xiaoyi","family":"Tian","sequence":"first","affiliation":[{"name":"University of Florida, Gainesville, FL, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zak","family":"Risha","sequence":"additional","affiliation":[{"name":"University of Pittsburgh, Pittsburgh, PA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ishrat","family":"Ahmed","sequence":"additional","affiliation":[{"name":"University of Pittsburgh, Pittsburgh, PA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arun Balajiee","family":"Lekshmi Narayanan","sequence":"additional","affiliation":[{"name":"University of Pittsburgh, Pittsburgh, PA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jacob","family":"Biehl","sequence":"additional","affiliation":[{"name":"University of Pittsburgh, Pittsburgh, PA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"320","published-online":{"date-parts":[[2021,4,22]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1109\/ICACCS.2019.8728499"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1080\/08993400412331363823"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1080\/08993408.2014.963363"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1145\/611892.611930"},{"key":"e_1_2_2_5_1","volume-title":"Social Network Chatbots for Smoking Cessation: Agent and Multi-Agent Frameworks. 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