Open source software has become a cornerstone of modern application development, but its widespread adoption requires understanding and navigating the nuances of open source licenses to avoid potential legal pitfalls. Organizations must be aware of the specific obligations tied to each license to minimize compliance risks. Traditionally, licenses were tracked using manual methods, but as software supply chains have grown in complexity, machine-readable licensing standards like SPDX or CycloneDX are now being adopted to gather and analyze licensing data. The lack of explicit licensing is a significant risk, with 14% of packages having unknown licenses, while license changes can result in copyright violation consequences. Conflicting licenses between package managers and source code repositories also pose challenges, with over 82,000 packages experiencing conflicting information. Permissive vs. copyleft licenses impose different obligations, while emerging licenses like non-commercial and ethical licenses require organizations to stay informed about the evolving landscape of open source licensing. The intersection of AI and open source licensing raises unique challenges, particularly regarding intellectual property rights and compliance with existing open source licenses.