Progressive design-build (PDB) has been successfully administered and executed in the private, airport, transit, and water/wastewater sectors. Although these sectors have experienced successes with PDB, there is limited use of this on highways. There has also been little information that provides guidance for highway agencies who are interested in implementing PDB. To address this gap, this paper investigates the common challenges associated with executing PDB in highway projects. These challenges include (1) legislative restriction, (2) lack of owner education, (3) demand on owner resources, and (4) lack of industry interest. The paper also provides a deep dive into the legislative restrictions of all 50 US states. Specifically, the result shows that five states allow design-build (DB) with a qualifications-based (QBS) and/or negotiated procurement, 13 have language ambiguous or supportive of DB with a QBS, 14 have a pricing component requirement in DB procurement, and nine have language restricting PDB. The findings of this paper were based on data triangulation of the following sources: (1) content analysis of 26 PDB documents including five manuals, eight published case projects, 14 industry presentations, and four academic publications; (2) nine interviews of owner representatives familiar with PDB; and (3) case studies of Maryland's Interstate 270 and Utah's US 89 project. By discussing PDB challenges, this research adds value to both industry and academia by presenting the first investigation of the challenges associated with PDB's use in the transportation sector. (C) 2019 American Society of Civil Engineers.