Sanctions should improve business compliance and mitigate the risks of non-conformity. This premise motivated our research and led to very interesting results for the trinomen business performance—transport infrastructure and local development strategies—public control. We used a customized Brunswik lens model to illustrate the decision-making process based on the interactions between the analysis of sanctions in the transport sector and the projected financial judgement, as we have traditionally understood and experienced them. We clustered 186,671 cases of noncompliance sanctioned by the Romanian authorities and created a chromatic map with accents on the risks of nonconformities. We employed principal component analysis to find patterns and correlations between faulty behavior in transport activities and the evolution of financial indicators, such as exports and imports. The ROC curve was used to investigate the credibility of a possible connection between transport sanctions and the development of regional exports and imports. We found multiple challenges that interfere with the projection of a trustworthy financial judgement in transport and offer insights and recommendations for integrated local governance practices and strategies aimed at mitigating the risks of noncompliance and promoting sustainable development in transport.