Arduino IDE Debugger

This maybe a silly question I’m little new to Arduino and Heltec WiFi LoRa 32 (V3) is my first controller.
I’m using Arduino IDE 2.3.2 on OS X, I believe I have everthing setup correctly, I can upload code to the board and it runs correctly on it.

I just can’t get the debugger to work. So my first question is it supposed to work?
If it is what could I be missing?

When I’m try to us it I keep seeing errors such as:

Info : only one transport option; autoselecting ‘jtag’
Info : esp_usb_jtag: VID set to 0x303a and PID to 0x1001
Info : esp_usb_jtag: capabilities descriptor set to 0x2000
Info : Listening on port 50001 for tcl connections
Info : Listening on port 50002 for telnet connections
Error: esp_usb_jtag: could not find or open device!

I have this resolved.
I didn’t know that “debug probe” hardware was needed.