This chapter provides an overview of how US securities regulation applies to the sale of cryptographic tokens using a distributed ledger, so-called initial coin offerings. Token sale transactions that meet the definition of ‘investment contract’ qualify as regulated securities transactions following the seminal 1946 court decision in the Securities Exchange Commission’s lawsuit against the W. J. Howey company. Currently, there exists substantial legal uncertainty regarding the regulatory classification of token sales involving utility tokens that provide their holders with non-financial, software-based functionality. As implied in a June 2018 speech by a high-ranking SEC official, sales of tokens may initially qualify as regulated securities transactions, yet later fail to qualify as regulated investment contracts if the tokens’ underlying network becomes sufficiently decentralized. Distributed ledger technology is disrupting the nature and operation of early-stage fundraising and access to software services and enabling the sale of digital tokens that operate as a cryptocurrency or provide access to a software service through the use of a blockchain or distributed ledger. The sale of such tokens, so-called initial coin offerings (‘ICOs’), is often in exchange for cryptocurrencies, such as Ethereum or Bitcoin (however, tokens could be sold in exchange for fiat currency). From January to May 2018, globally US$13.7 billion in tokens were sold by 537 companies or projects, an amount greater than all previous time periods combined. This chapter discusses under what circumstances US securities law applies to the sale of such tokens.