This study examines limitations of the current regulatory framework for tobacco advertising on Instagram. We first investigate compliance with Food and Drug Administration (FDA) warning label requirements for posts by tobacco-owned accounts. Next, we examine the prevalence of content that has been restricted in broadcast or print for its youth appeal, followed by content meeting more expansive criteria for youth appeal set forth in the FDA's guidance document. Posts by tobacco-brand-owned accounts between January 1, 2021, and February 14, 2022, were sampled from Mintel's Comperemedia Omni database. Instagram posts from 15 accounts were examined for violations of FDA warning label requirements and content that has been restricted on other mediums, including cartoons, sports branding, unauthorized claims, and young models (N = 1243). Finally, a subsample of n = 453 unambiguously branded posts was coded for themes that met the FDA's criteria of resonating with younger audiences, particularly that "adolescents rely on external information as they seek to shape their own identities." Only 12.8% of posts had fully compliant warning labels. Content that has been in some way regulated on other mediums, such as cartoons (1.6%), unauthorized health claims (<1%), sports branding (<1%), and young models (4.4%) were infrequent. However, a conservative analysis focusing only on branded posts found that posts frequently highlighted tech elements (45%), device customizability (24.5%), vaper identity (17.7%), stylized product photography (33.6%), social media engagement (32.2%), and memes (5.7%). Enforcement of existing regulations on Instagram is minimal. Explicit content restrictions applying evidence-based guidance on youth-appealing advertising are needed. This research has important implications for enforcing and expanding advertising regulations on social media. First, Instagram's self-imposed regulations are ineffective, permitting tobacco companies to post ads from brand-owned accounts despite claiming to restrict tobacco promotion on the platform. Second, policymakers should seek to apply FDA guidance on youth-appealing advertising informed by decades of research to create explicit enforceable content restrictions that extend beyond cartoons, sports figures, and young models to include content likely to situate tobacco use within the developing self-concept of vulnerable youth such as presenting e-cigarettes as hi-tech devices, highlighting vaper identity, or infiltrating online social media culture. Finally, greater resources for enforcement are needed given the only applicable regulation, warning labels, remains largely ignored.