This paper presents a case study of the Manitoba experience in permitting petroleum-related oversize/overweight (OS/OW) truck traffic. In recent years, Southwest Manitoba, along with many regions throughout North America, has experienced rapid growth and change in the petroleum industry. This growth has fuelled economic development and also caused infrastructure challenges on rural roads that are being used by unique vehicle configurations, many of which are beyond basic truck size and weight (TSW) limits. Manitoba's OS/OW permitting program for these vehicles stems from the performance-based approach to TSW regulation being used in Canada since 1988 and relies on ongoing collaboration with the petroleum industry. Manitoba's experiences have led to several insights, which may be options for other jurisdictions facing similar issues related to OS/OW petroleum-related trucking. These insights include: (1) purposeful collaboration with the industry and officials in neighbouring jurisdictions to understand permitting needs and barriers; (2) supplementing qualitative understanding of the industry with quantitative data; and (3) identifying opportunities to expedite permitting procedures by issuing annual permits to routinely-configured vehicles, utilizing technologies to assist with TSW enforcement, and rationalizing permit fee structures.