The shift to online learning management systems such as Canvas seemed to assume students would become more independent and self-regulated, yet little research has been conducted in this area, especially with school-age students. This study examined the ways middle school students engaged with an online learning management system (LMS) and their perceived impact of the LMS on building executive functioning learning behaviors. A mixed method explanatory sequential study was conducted at an independent Jewish school in the northeast region of the United States. A standardized online social-emotional assessment was used to determine the executive functioning profile scores (e.g., beginner, intermediate, and advanced) of 28 students in grades six and seven. These students also completed a Canvas engagement survey. Purposive sampling was then used to select 10 students representing all three levels of the executive functioning profiles for semi-structured interviews. Quantitative analysis revealed insignificant correlations between students' executive functioning profile levels and their Canvas engagement levels. Executive Functioning Beginners were found to have limited engagement in the LMS. Executive Functioning Intermediates were found to have most consistent use of the LMS, with 80% stating they used the LMS calendar and 50% stating they used the to-do list. Executive Functioning Advanced students seemed to choose to either actively engage or not engage at all with LMS. Qualitative analysis further revealed students felt the LMS made submission of assignments easier, helped to centralize all course materials and grades into one location, was a useful backup for their memory, and made completing make-up work easier. However, they communicated that the LMS became less helpful when teachers forgot to post some materials and when each teachers used it in different ways. These findings suggest middle school students' executive functioning level determines middle schoolers' engagement with the LMS and that teachers' use of LMS can help or hinder students' engagement with the LMS. Implications of the study for evaluation of new school technologies, and development of school curricula, systems and policies are discussed. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]