Esp-prog debugging on a Mac - no device found

FYI, I’ve deleted your duplicate post in Failed to launch GDB - WROVER, ESP-Prog, otherwise we’re opening up two topics where this is discussed…

Can you show a picture of your setup and what cables you connected to where? The platformio.ini shows a esp-wrover-kit is being debugged which has the onboard debugging tool debug_tool = ftdi but you redefine it to debug_tool = esp-prog so I guess you have custom board that is not actually a ESP Wrover Kit?