The neuro-enhancement Modafinil promises to dramatically increase users' waking hours without much sacrifice to clarity of thought and without serious side effects (inducing addiction). For Modafinil to be advantageous, its usage must enable access to goods that themselves improve the quality of one's life. I draw attention to a variety of conditions that must be met for an experience, activity or object to improve the quality of one's life, such as positional, relational, and saturation conditions, as well as it's being good for its own sake. I discuss and describe the contexts in which widespread usage (legal or not) of Modafinil would undermine these conditions being met, and thus users would fail to significantly improve the quality of their lives and would in fact potentially make both themselves and nonusers worse off in important respects thus far overlooked by critics. In the right contexts, where free time is protected and prolonged, Modafinil does have a variety of potential benefits including, most interestingly, a distinctive form of agency possible only in free time. The potential disadvantages and advantages highlighted in this article are relevant not only to public institutions deciding whether to legalize Modafinil's use as an enhancement but also to individuals deciding whether to use it illegally, as well as to the questions of how and whether to alter key features of one's context (e.g. regulating work hours or extending social services) rather than, or in addition, to regulating the use of enhancement drugs such as Modafinil.