A reliable transportation network is essential to maintaining and growing a region's economic productivity through the movement of goods, a significant proportion of which is moved by truck. Criticalities in the network should be identified and mitigation measures implemented to ensure that minimal negative impacts arise from link disruptions. Using criticality measures that account for network, freight flow, and economic characteristics, a comparison is made among locations of highly critical segments in the province of Ontario, Canada, and infrastructure improvement projects planned by the Ministry of Transportation of Ontario. Four highway capacity expansion segments are explored through a scenario analysis, comparing the effects resulting from their implementation to a status quo base case. Freight and passenger flows are forecasted to the year 2036 for the analysis. A comparison is made among the scenarios to assess the network‐wide impacts of each segment's improvements with respect to vehicle and shipment value flows, travel time, greenhouse gas emissions, and each segment's average operating conditions. Of the four segments compared, the improvements of Highway 404 appear to provide the most significant benefits with respect to network performance. Such analysis can inform policy measures for the prioritization of infrastructure improvements to address network criticalities.