I have here an ESP32-WROOM32 and want to use it as BT to MQTT gateway and try to install the regular esp32dev-ble image. But at the end every time it comes “Installation failed Failed to initialize. Try resetting your device or holding the BOOT button while clicking INSTALL.”
I tried also to press the boot button during plug it on the Notebook before flasing.
In the last few days, I have often worked with the upload tool, and I also own an ESP32‑WROOM‑32. I have exactly the same problem: it seems that this board has some difficulty entering firmware download mode.
Personally, I have never found a real solution. As a last option, I unplug the board from USB, plug it in again, and try once more: first pressing the RESET button and then immediately the BOOT button. I found this information around the Espressif official guide ( ESP32-DevKitC V4 - ESP32 - — esp-dev-kits latest documentation ).
I am not sure if this is the same case for you (and for me as well), but I hope this information is useful.