How can I flash my wroom devkitc without holding the boot button under a ubuntu VM guest?

[paparika]

Recently I migrated to a virtualbox ubuntu18.04 guest(win10 host), it works fine. but I noticed I had to hold the boot button when I was flashing under my guest os while this step is unnecessary under my host os.
It's very inconvenient so my question is if there is any way to solve this? Thanks!

[paparika]

btw, I also noticed I don't need to press any button on tinypico when flashing it under my ubuntu guest.

[ESP_Sprite]

The autoreset trick is somewhat dependent on the timings the driver/OS/VM impose on the process; it could be that pulling everything through the VM is slowing it down too much. Aside from software tricks (looping through the serial port vs looping through the USB device to the VM), you can also see if adding an 1 - 10uF capacitor between GND and EN of the ESP32 helps.

[paparika]

The autoreset trick is somewhat dependent on the timings the driver/OS/VM impose on the process; it could be that pulling everything through the VM is slowing it down too much. Aside from software tricks (looping through the serial port vs looping through the USB device to the VM), you can also see if adding an 1 - 10uF capacitor between GND and EN of the ESP32 helps.

Thanks for your advice!