Debugging Heltec WiFi LoRa 32 (V3) with ESP Prog Debug Probe

I am having problems flashing my Heltec V3 board with my firmware using the ESP Prog debug probe. I am able to build my firmware without problems, but flashing results in these errors:

I followed the guide specified here to install the driver for the ESP prog, and also reflected the configuration settings in my platform.ini file:

https://docs.platformio.org/en/latest/boards/espressif32/heltec_wifi_lora_32_V3.html#configuration

Here are my ini file definitions as well:

[env:heltec-v3]

platform = espressif32

board = heltec_wifi_lora_32_V3

framework = arduino

upload_protocol = esp-prog

extends = esp32s3_base

debug_tool = esp-prog

debug_init_break = tbreak setup

board_check = true

//Temporary until espressif creates a release with this new target

build_flags =

${esp32s3_base.build_flags} -D HELTEC_V3 -I variants/heltec_v3

-DGPS_POWER_TOGGLE ; comment this line to disable triple press function on the user button to turn off gps entirely.

I have double and triple checked my wiring for the 4 debug signals, power and ground. I also tried powering my MCU and the probe independently as opposed to the shared 3.3 or 5V pins. I also double checked the driver installation and I am getting a connection on my COM Port. Any help is appreciated.

Update: I fixed this error, but now I am getting this

A fatal error occurred: Failed to connect to ESP32: No serial data received.

To me, it may be an issue with the Heltec board not being in an obvious boot state to allow firmware flashing. I have confirmed debug probe connection via pio device list, and the green LED flashes as it attempts to connect to the esp32s3.