Despite ambitious visions of creating utopian digital communities powered by blockchain technology, several attempts to build “cities on a hill” have hit roadblocks. Regulatory hurdles, unrealistic financial projections, and evolving technological realities have led many such projects to falter. 2020’s failure of the MS Satoshi, an attempt to create a Bitcoin city at sea, exemplifies this trend. Another notable example is Trump’s Gaza Riviera plan, which aimed to tokenize land in the disputed territory. Though initially touted as a solution for economic displacement, the project remains stalled and faces legal challenges. Even CityDAO, a pioneering decentralized organization attempting to establish its own city on blockchain, found itself facing difficulties due to zoning regulations and community disagreements. Akon City, envisioned by singer-entrepreneur Akon, faced similar struggles, ultimately abandoning his ambitious project. These failures paint a picture of the complexities surrounding implementing decentralized city models on blockchain. While technological innovation and the promise of financial freedom remain strong motivators for these endeavors, challenges in securing resources, navigating regulations, and fostering sustainable communities require more than just blockchain technology to succeed.