The authors combined their interests in improving corrections and information technology to examine how the variables correctional education using technology (or eLearning) are artfully used to educate prisoners to reduce recidivism and improve reentry. To address the issue, the authors conducted an extensive literature review and using a set of criteria (study sample size, definition of recidivism and eLearning) conducted a comparative analysis of 35 research studies published in referred journals. The analysis reveals insufficient research on correctional education, namely eLearning programs. The authors conclude that the data collection challenges and technology security concerns may not outweigh the champion of using the eLearning mode to education prisoners and association with improved recidivism and reentry.