Across the globe, an ongoing urban food system (UFS) transformation has made street food trade (SFT) fundamental for urban food security (FS). It also highlights the central role of city governance in SFT. However, large gaps exist in understanding of the regulatory arena, that constrains policy discussion, hinders traders, and inhibits access, affordability, and availability of safe street food. This paper examines implications of SFT regulations on FS and urban livelihoods. We focus on a cross-section of 260 street food enterprises (SFEs) in urban Kumasi, Ghana, and explore interactions of compliance with SFT regulations, adoption of improved practices, enterprise performance and their links to FS in UFSs. We find that though vendors are generally aware and willing to invest in improved practices, compliance levels with regulations are below average due mainly to insufficient, inconsequential, and uneven regulatory enforcement. We also find that compliance costs are high whilst detected non-compliance neither bears sufficient legal nor financial consequences. Lastly, compliance requirements negatively impact urban FS such that, annual compliance costs inhibit the supply of over 103,000 food servings from the UFS whilst compliance-induced innovations siphon out over half a million food servings from it annually. The later also increases prices of street-vended food by about 6%. From a modern urban food policy perspective, our findings suggest urban food policy and city management efforts could enhance the FS role of SFT, if they prioritize promoting improved practices, simplifying regulations, and assisting vendors in compliance.