>Are the gnd of your cable and the ESP chip connected?

Yes, they're connected. I'm interested in hearing what else I might try to address connection problems.

I have made some progress - I'm able to do a simple flash but my full featured flashes are failing either via serial or OTA.

> This is for ESP8266 and an ESP32 is a different beast. Yes, I'm attempting to flash a ESP8266, specifically the 8285 variant. Yes, I used an ESP32 to verify my setup is working as its the closest match I have. >and how you're trying to program it. I'm using esptool as shown in the console output I...

I'm attempting to flash but keep running into this problem. I'm able to flash an ESP32 without problem so I think my serial port and cable are fine. Is there a way to fix it? ➜ esphome esptool.py --before default_reset --after hard_reset --baud 115200 --port /dev/cu.usbserial-ABSCDMU6 --chip esp8266...