This study examined how community college students' reflective sentiments about learning with the Intelligent Tutoring System (ITS) ALEKS evolved in three developmental pre-Algebra Mathematics courses and how students' sentiments related to their metacognitive awareness and learning performance. Thirty-nine students participated in this study. ALEKS was used as a supplementary aid to support self-regulated learning (SRL), which is important in both online and in-person learning. SRL is important in mathematics learning contexts, in both online and in-person classrooms. Sentiments regarding ALEKS and their experience in the course were provided by students in five open-ended reflective prompts in the middle and at the end of the course. Content analysis was employed to analyze students' reflective sentiments and thematic analysis was used to analyze student interviews. Students' metacognitive awareness was assessed early in the course using the Metacognitive Awareness Inventory (MAI). Students' perceptions regarding the use of ALEKS in developmental math courses were collected through Zoom interviews. Thematic analysis revealed that students thought that ALEKS would be more useful in a 16-week semester, but not a six-week mini-term course. Three themes emerged: student challenges with ALEKS, student appreciation of ALEKS, and alternate uses of ALEKS. Students' reflective sentiments regarding using ALEKS improved over the course of the term and their objective performance increased from midterm to final exam. Qualitative and quantitative findings suggested that students' feelings towards ALEKS generally improved together with their perception of their performance in the course. More than half of participants reported positive feelings regarding ALEKS in both their pre-midterm and pre-final exam survey. In addition, perception of performance in the course increased from midterm to final exam. No metacognitive awareness factors correlated with students' sentiments regarding ALEKS. Results suggest that instructors should use ALEKS in 16-week semester courses and align ALEKS use to course content. As the semester unfolds, students realize the usefulness of ALEKS and change their negative sentiments towards it. Thus, instructors should explain the SRL value of using ALEKS early in the course because students who have positive ALEKS sentiments at the beginning of the course perform better than those who have a negative disposition. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]