In 2020, a wave of public tech companies—including The RealReal, Vroom and Redfin—began selling record amounts of ultra-low-interest bonds that would convert into shares if the companies’ stocks kept soaring. Instead, stocks have been crushed, and a wall of potentially crippling or course-altering debt now looms over some firms.

Several companies that sold convertible debt likely will struggle to refinance it or find the cash to pay it off unless their fortunes turn around soon, according to interviews with investment bankers and an analysis of companies’ financial statements. If they do refinance, it will likely be much pricier. For some companies, the crunch could lead to efforts to sell themselves.