Project Management (PM) tailoring involves adapting PM approaches to fit specific project needs. Although the literature acknowledges the importance of tailoring, the concept often remains vague, and there is a lack of practical studies in specific contexts, such as Public Procurement (PP). This paper investigates the reasons for tailoring and its main targets in three large public construction projects in Italy, where the authors were directly involved in adapting PM approaches. The findings reveal common patterns across all cases: (i) the need for tailoring emerged during the execution phase; (ii) the main driver was the need to improve monitoring and control while complying with the complex legal and bureaucratic environment typical of public sector projects; and (iii) to reconcile the needs of project managers with the PP environment, tailoring the tools, namely the Project Management Information Systems (PMIS), emerged as the only viable option. The paper also offers reflections on tailoring as a meta-project and on its economic sustainability.