Something is physically wrong with the connection, the line or the adapter configuration.
- How did you make the connections? Did you follow the wireup from @manuelbl’s tutorial (https://medium.com/@manuel.bl/low-cost-esp32-in-circuit-debugging-dbbee39e508b)?
- Have you tried lowering the adapter speed in case of bad / long cables or connections? Refer ESP32 + J-link debugger does not start - #12 by Yourigh. However note that you have to modify
esp-wroom-32.cfginstead as that is the chip on the board you have configured (ref)