The topic of study was communication technology preferences of online students and online instructors. The generational cohorts of each group were all assessed to see if preferential differences existed due to age. The research problem was that technical generational differences cause challenges with effective communication between faculty and students in the online academic environment. Supported by a combination of the transactional distance and generational theory, the purpose of this quantitative comparative study was to identify and compare the communication modes that online students and online instructors prefer to use to communication with each other for academic purposes. Data was collected through surveying and analyzed by means of ANCOVA. There were 271 participants, whereas 81 were online instructors and 190 were online students. ANCOVA found no significant difference between groups controlling for age F (1, 267) = 0.001, p = 0.972, where p > 0.05. This outcomes of this study support previous research conducted by Chang et al. (2016) and Bailie (2017) that email is the preferred means of interacting in distance educations. This study also supports Severt et al. (2013) and Skidmore et al. (2014) in that generation X and millennials prefer electronic technologies for collaborating. It is recommended that practioners in distance education create standardized communication mode policies so that both online students and instructors know which technology to use so that a sense of connectedness is established to enhance academic success. More research is needed as communication technology advances and newer generations reach college level age. [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.]