The COVID-19 outbreak accelerated the growth of work from home at many enterprises. An important factor enabling collaborative work from home was the use of video conferencing, shared development project work tools, and other technology-driven resources for virtual enterprises. Given that many employees are choosing to remain working remotely from the office on at least a part-time basis, software companies need to reassess and update their policies and practices regarding the protection of intellectual property, particularly trade secrets. The phrase commonly used in the law regarding trade secrets is “reasonable measures.” While certainly under the umbrella of security practices to protect against hacking and malware, reasonable measures to protect trade secrets often involve different, albeit related objectives. There are numerous best practices and policies that warrant review and potentially adoption, but managers face the dilemma of choosing which policies and practices to adopt since such policies and practices can be costly and create unnecessary constraints for employees, customers, and other stakeholders. Obviously, no one wants their organization to devote the time, money, and other resources to working with legal counsel to litigate misappropriation of trade secrets. Prevention is the preferred alternative. Managers, however, need to decide, “how much is enough” regarding reasonable measures what we label the Goldilocks Dilemma. This paper provides a review of reasonable measures that can be considered and used by software companies when assessing and adopting measures to protect their intellectual property, particularly trade secrets.