Ashley Ebersole, a former SEC legal advisor, has identified regulatory engagement as the primary challenge for the compliance of real-world assets (RWAs) in the crypto space. Ebersole, who served at the SEC from 2015, highlighted that enforcement-heavy policies between 2017 and 2019 hindered RWA development. He noted a decline in communication between the SEC and crypto firms post-2021, though recent leadership changes, including Paul Atkins' appointment, have fostered improved dialogue. Ebersole suggested a compliant token model akin to depositary receipts to navigate these challenges, while also cautioning about jurisdictional and revenue-related issues, such as Countering the Financing of Terrorism concerns. Despite these hurdles, the tokenization of RWAs is gaining momentum, with major players like Robinhood, BlackRock, and JPMorgan entering the market.