Online shopping technology is important as it helps businesses to gain value from lesser operational expenditures due to the reduced workforce and physical space. Despite its benefits, the adoption of online shopping in Africa, including Namibia, lags. Hence the main objective of this research is to investigate the challenges and issues in adopting online shopping for market growth. Adopting a qualitative approach based on the UTAUT model we determine and analyze predominant challenges and issues, examine the influence of demographic variables on online shopping, define and investigate the key success factors and propose strategies to increase the adoption of online shopping. Findings reflect that lack of security and trustworthiness in the online shopping process is a key challenge in the adoption of online shopping. Recommendations include that the government should regulate online shopping procedures to protect consumers and prevent cybercrime and businesses should offer consumer education to build trust and eliminate fear in the online shopping process.