What you mean with a C9 that is cracked?, I have a custom board that have this behavior too

What Chip part number are you using?, Mine is ESP32 WROVER IB on a custom board. EN Pin is pulled up to a 10K resistor with a 1uf cap to ground, the GPIO0 Pin pulled up with a 10k resistor. To enter to flash mode as usual, EN pin short to ground then Boot Pin short to ground and release Boot after E...

I facing the same Issue on a ESP32 WROVER-1B CHIP ESP32-D0WD (revision 1) Enable Pin eventualy goes low after a few minutes, what is funny that iron heating up the castellated solder joints again "removes" the short, after this I can flash the chip again with arduino IDE and with esptool without giv...