Transactional distance theory (Moore, 1973, 1993, 2013, 2019) identifies transactional distance as a psychological or communication gap that can be perceived by learners based on their personal educational needs and/or preferences. These perceptions of distance can occur in any learning environment but especially in distance learning or online learning environments and can influence course satisfaction, participation, and persistence (Tinto, 2009). Perceptions of transactional distance are observed through interactions (learner-instructor, learner-learner, learner-content; Moore, 1989) and are influenced by the theory's three main tenets of course structure, dialogue, and learner autonomy through instructional design and personalization. Qualitative interviews were conducted with Black males taking online asynchronous math courses at a mid-sized southern university to determine how the participants' perceived instances of transactional distance in their online asynchronous math courses. Semi-structured qualitative interview questions were developed based partly on Monica Aixiu Zhang's quantitative measuring tool (2003) for measuring transactional distance based on learner interactions (learner-instructor, learner-learner, learner-content, learner-LMS, and learner-institution) which was updated by Paul et. al. (2015), including Zhang in 2015. Perceptions were recorded, analyzed, and organized per tenet and type of interaction. Results of the study support the theory's purport that learners perceive levels of transactional distance based on their personalized educational needs and/or preferences. The findings also support empirical research findings stating that educational disadvantages can be exacerbated in distance learning environments, especially for marginalized or underprepared populations (Paul et al., 2015; Salvo et al., 2019; Stewart et al., 2010; Xu & Jaggars, 2013). Reportedly, the findings of this study support the need for learners to experience varied interactions with options available to meet their personal educational needs and or preferences. Participants experienced levels of transactional distance concerning dialogue within the learning environment, concerning autonomous learning management and support, and concerning their reactions to course structures based on their personalized needs and preferences. Instructors, instructional designers, and stakeholders have the opportunity to support learners through professional development for instructors and course designers, cycles of feedback, learner support programs, options for personalization, and varied course design which should include interactions, dialogue, opportunities for autonomy, and course structures appropriate for online learning environments. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]