WASHINGTON—Regulators’ efforts to push cryptocurrency startups to comply with laws governing fundraising may be faltering, as several firms that agreed to fix past misdeeds missed deadlines to repay investors or provide more transparency.

The firms collectively raised about $40 million through illegal sales of digital tokens during the height of the cryptocurrency boom in 2017, when over $5.4 billion was raised. In exchange for paying lower fines, the companies were supposed to meet the Securities and Exchange Commission’s…

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