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In designing learning technology, it is critical that the technology supports both learning and engagement of students. However, achieving both aspects in a single technology design is challenging. We report on the design and evaluation of Gwynnette, intelligent tutoring software for early algebra. Gwynnette was deliberately designed to enhance students’ algebra learning and engagement, integrating several playful interaction and gamification features such as drag-and-drop interactions, an alien character, and sound effects. A virtual classroom experiment with 60 students showed that the system significantly enhanced both engagement and conceptual learning in early algebra, compared to the older version of the same software. Log data analyses gave insights into how the design might have affected the out-comes. This study demonstrates that a deliberate design of learning technology can help students learn and engage well in an unpopular subject such as algebra, a challenging dual goal in designing learning technologies.