Digital transformation has become a priority for all major companies. This is being driven only further by the spread of artificial intelligence’s commercial use cases and ever-tightening data protection and cybersecurity regulations. However, procuring enterprise software (concerning both the development of custom-made software and “off-the-shelf” software developed for mass use) may give rise to various legal issues. Promptly identifying and addressing these issues can help prevent considerable legal and operational expenses, as well as other inconveniences.