This paper discusses the formation of habits with the help of self-tracking technologies. Although devices like Fitbit smart bands come with promises of empowerment through the means of increased control over users’ habits, existing literature does not provide conclusive findings about the validity of such claims. It contributes to the ongoing debate by relying on John Dewey’s pragmatist philosophy and its notion of intelligent habit. I demonstrate that from a pragmatist standpoint, habits that are the most likely to accomplish users’ goals contribute to their flourishing need to be reflective (accompanied by adequate deliberation) and flexible (adaptable to the changing circumstances). On this basis I highlight some ethical-epistemic issues surrounding self-tracking technologies that inhibit the formation of habits desirable from a Deweyan standpoint. These include a lack of reflection on the part of the developers, difficulties for users to deliberate and consciously shape the habits developed by their devices, and dependence upon self-tracking tools that makes it difficult to adapt habits to individual needs and circumstances. I conclude the paper by discussing self-tracking’s general impact on flourishing, as well as placing my arguments in the context of the diversity of self-tracking practices and identifying how users attempt to alleviate the shortcomings of the technology and make it more suitable to their goals and needs.