can't flash board when connected to JTAG device

[little-jim]

I have an ESP32-DevKitC-32UE Development Board (linked below) that, when connected to a MacBook M1 flashes just fine. I also have a brand new JTAG board: ESP-Prog Program Downloader Automatic JTAG Debugging Board for ESP8266 ESP32 (link also below). The pins are connected correctly. Checked, rechecked and checked so many damn times. However, the ESP32 will not flash when connected via the JTAG board. When connected, the jtag/esp32 show up as the following ports:
/dev/cu.usbserial-12300
/dev/cu.usbserial-12301
/dev/tty.usbserial-12300
/dev/tty.usbserial-12301
I've tried all four ports and on none of them can I flash via the jtag board
https://www.amazon.com/gp/product/B087T ... UTF8&psc=1
https://www.amazon.com/dp/B08P3NM4QS?ps ... ct_details

I have installed the FTDI_VCP driver and the CP2102 drivers. Did not help.

I also have exactly the same issue on an Ubuntu box. Both boards are brand new so I'm thinking I've done something wrong, as opposed to the JTAG board being defective. Does the enable pin on the ESP32 need to be connected to the JTAG board? The pinout for the board does not show a TRST pin but other JTAG boards do have one