Endgame thinking means transitioning from merely trying to ‘control’ the tobacco epidemic to developing plans and measures to bring it to an end within a specific time, by changing the underlying dynamics that have created and perpetuated it for more than a century. Among the innovative policies characterised as ‘endgame’ policies are so-called ‘tobacco-free generation’ or ‘smoke-free generation’ policies, which prohibit sales of some or all tobacco products to individuals born on or after a particular date. Such birthdate-based sales restrictions (BSR) have intuitive appeal, largely because they do not appreciably disrupt the status quo of retail sales, which continue unchanged for all those born before the designated cut-off date. They also hold the potential for further denormalising tobacco use and sales by anticipating the long-term end of tobacco sales. In this Special Communication, we analyse BSR policies through an endgame lens and propose questions that should be discussed in jurisdictions considering them. We suggest that this policy has potential underexamined pitfalls, particularly related to equity, and that if enacted, it should include policy guardrails and be part of a package of endgame measures.