Internet-based attacks issue still terrifies the Internet community including the individuals and employees at public and private organizations. Many solutions were proposed to protect the Internet users against cybersecurity attacks. Most of the solutions target the technical side of information systems. Attackers, therefore, still able to bypass technical-based solutions through the human unawareness factor. Therefore, organizations have to implement effective training programs to enhance their employees’ security awareness and influence them to comply with security rules and policies. The problem which still exist is the challenges that confront the implementation process of effective security training programs. That is why, security training challenges need to be analyzed to highlight the factors that limit the success of training programs. In this paper, security training challenges are categorized into three types based on which aspect they occur and cause impacts. The challenges are categorized as; organization-related challenges, trainees-related challenges, and training program-related challenges