Information security is becoming a key organizational concern in light of increasingly demanding regulations, customers’ apprehension, and, significant operational risks. The information security practices of employees are pivotal for preventing, detecting, and responding to security incidents. This paper is synthesizing the insights from prior research based on a systematic literature review that explores challenges related to information security practices in organizations and the ways these challenges are managed to avoid security breaches. Four general challenges are identified: (1) security rules and procedures, (2) individual and personal risks, (3) culture and security awareness, and (4) organizational and power relations. To manage these challenges, three types of measures are prominent: measures related to training and awareness, measures related to organizational support, measures related to rewards and penalties. These measures aim to enhance systemic capabilities and to adapt security mechanisms to the idiosyncratic characteristics of organizations.