This research provides a comprehensive analysis of deontic expressions within the Code of Federal Regulations (CFR) Title 48, Federal Acquisition Regulations System, specifically focusing on obligations, permissions, prohibitions, and dispensations. Utilizing SHAMROQ, a systematic and rigorous methodology, the authors extract, classify, and analyze these expressions, quantify their prevalence, and identify common linguistic patterns within the legal text. The results show that obligations (71.3%) form most deontic expressions in CFR 48, indicating the heavily prescriptive nature of the document. Permissions also form a significant part (21.9%), suggesting the liberties and allowances are embedded within the regulatory framework. In contrast, prohibitions (5.4%) and dispensations (1.4%) are less frequent, indicating that the document leans more towards defining what is required or allowed rather than what is explicitly forbidden or exempted. This research also highlights the challenges encountered during the extraction process, providing insights into the complexities of parsing legal texts and the intricacies of deontic language. These challenges range from the technical difficulties of parsing a complex hierarchical document to the conceptual challenges of defining precise rulesets for regulations and provisions. In summary, the results deepen the understanding of regulatory compliance in software engineering and contribute to the development of more effective and efficient automated extraction tools.