unable to flash ST17H66B

[bsdinis1]

I am using a WeAct Studio ESP32-S3-B board's CH340K to flash, with CHIP_PU / Reset tied to GND. This board contains an SOT-223 AMS1117-3.3 which should be able to handle up to 800mA~1A of current draw.
Since we're using the serial adapter on the board rather than the ESP32-S3 itself, "TX" is RX and "RX" is TX.

This ST17H66B board does not power on with a fully charged CR2032, neither with a pair of fully charged AA alkaline batteries in series, it beeps and lights the LED very briefly and then dies immediately. But it does power on with the ESP32-S3 board's 3.3V output.

BAT+ Red                 -> 3.3V
GND Black                -> GND
VPP Yellow (P10 / pin 6) -> RX (labeled TX on the ESP32-S3 board)
P9 Blue (pin 5)  ->  R2  -> TX (labeled RX on the ESP32-S3 board)

The buzzer starts chirping when I execute the Python script but then it does nothing, when I unplug and reconnect BAT+ some garbage is printed in the terminal but it never gets past this stage no matter how many times I reset the ST17H66B board.
If I reverse TX and RX then I never hear the chirping.

A couple of notes; I wasn't able to solder the blue wire directly to P9 as my wires are too thick to solder them directly to the MCU pins and the only other available place to solder it to would be the right side of the R2 resistor on the Base of Q1 which is too small for my wires.
The blue wire is soldered to the Base of Q1, so R2 is between the ST17H66B and the CH340K. The base resistor is about 500 ohm (0.5k). The blue wire looks like it is touching the Emitter pin but it is not, and neither is it bridging R2.
I am unable to power on the ST17H66B board while yellow (P10) is connected to RX, but it powers on fine after unplugging just the yellow wire. The device remains on after plugging the yellow wire back in.