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Warning labels have been mandated for cigarette packages under US federal law since the mid-1960s. While the nature and specificity of warnings has evolved, there is a long-standing skepticism about the effectiveness of textual warning labels, which has spurred the global use of pictorial warnings as a deterrent mechanism. Due to commercial speech challenges, the USFDA has delayed adoption of graphic cigarette labels, and the impact of pending, newly revised graphic warnings remains a matter of uncertainty. Like other matters of smoking abatement, public health anti-tobacco initiatives are compounded by the rapid increase in e-cigarette use where currently, mandatory warnings are tepid, mirroring both lack of knowledge and regulatory inertia. This paper explores the trajectory of cigarette warning labels, using the Public Health Cigarette Smoking Act of 1969 as a jumping off point for tracing the evolution of package warnings from their origin to the present. Particular consideration centers on how warning labels can be strengthened in the context of e-cigarettes through revisions to the current tobacco regulatory process.