The permits governing longer combination vehicle (LCV) activity in Canada aim to leverage LCV productivity advantages relative to other truck configurations while subjecting LCV operations to stringent regulatory controls. As of 2016, nine of the 13 provinces and territories permit LCV operations on a 17 000 km highway network. This article synthesizes LCV regulations in these jurisdictions within five categories: (i) carrier permit requirements, (ii) truck size and weight limits, (iii) equipment requirements, (iv) operating conditions, and (v) driver qualifications. While jurisdiction-specific differences remain, the synthesis reveals regulatory uniformity at the regional level. The article identifies how these regulations influence highway design, operations, and management decisions concerning the accommodation of LCV performance characteristics, the spatial and temporal control of LCV operations, the eligibility of drivers and carriers to operate LCVs, and opportunities for regulatory harmonization. As LCV activity increases, the need to formally consider the characteristics of LCVs within these decisions becomes more apparent.