The study examined the use of digital diary as a tool for enhancing parental school involvement in Tanzania. The development of the digital diary followed eXtreme Programming agile method where 87 parents and 6 teachers from St. Florence school were involved. Parents and teachers were given six months to use the tool before testing for its effectiveness using data from 7 teachers and 156 parents through semi-structured interviews and questionnaires respectively. The study found that the majority of respondents (84.4% of parents and 96.7% of teachers) indicated that the digital diary was useful tool as enabled them to track children’s progress via their smartphones. Moreover, computer generated reports showed that messages to/from parents were delivered with approximately 90% success rate. This research argues for schools to adopt and use digital diaries for easy, engaging, and effective for better parental school involvement.