- Are you running windows on your laptop?
If so this utility is is handy for notifying you of new com ports without having to drill down into device manager: https://helmpcb.com/software/serial-port-monitor
- It can be tricky to get ESP32s into boot mode.
i) Power on / connect the ESP
ii) Start the flash tool connecting
iii) Press and hold both buttons on the ESP board
iv) Release the EN button while continuing to hold the IO0 button
v) When the flash tool discovers the device you can release the IO0 button.