Each learner brings a unique mix of personality traits, preferences, and talents to the educational setting. These factors can influence the extent to which learners are able to effectively deploy skills and strategies to achieve their academic goals. Gaining a deeper awareness of how specific personality traits play a role in the choice and deployment of SRL strategies provides opportunities to anticipate which learners might be effective or ineffective self-regulators. Doing so would enable instructional designers, educators, or higher education administrators to better plan and deliver effective educational experiences for a wide range of learners. The purpose of this study was to investigate the extent to which the use of SRL strategies was impacted by learner differences in Big Five personality traits. This mixed methods study examined the potential of utilizing the Big Five Inventory classification as a predictor of self-regulated strategy use. Specifically, the study investigated the relationship between the existence of openness, conscientiousness, extraversion, agreeableness, and neuroticism traits as possible predictors of learner use of SRL strategies. Results indicated that learners high in openness, conscientiousness, extraversion, and agreeableness were shown to be more skilled self-regulators than those high in neuroticism. Those high in neuroticism were less skilled self-regulators and tended to use help-seeking strategies more frequently than those in other personality trait categories. The qualitative findings highlighted the need for effective time management as an important self-regulation strategy, a preference for face to face versus an on-line delivery format, and a lack of motivation. However, responses did not seem to systematically vary by personality trait.