I tend to do an in-place update, since removing the whole Picade from the cabinet to update it is complicated. You can do this by locating the compile file, copying it to your Pi and using the updater here: https://github.com/pimoroni/Picade-Sketch/tree/master/update
But if you’re not using it with a Pi try grabbing this file:
Then:
Go to “Devices and Printers”
Find the Picade ( Leonardo ) and right click on it
Pick “Properties”
Click the “Hardware” tab
Click “Properties”
Click “Change settings”
Click the “Driver” tab
Click “Update Driver”
Click “Browse my computer…”
Click “Let me pick…”
Click “Have disk”
Click “Browse”
Find the picade.inf file
Click “Open”
Click “Next”
Click “Yes”
Click “Install this driver software anyway”
You should see: “Windows has finished insta…” “Pimoroni Picade”
This is basically because the Arduino IDE resets it, then sits waiting for a new serial port to pop up, and then downloads to that new port. If it can find it!
I’d wholly recommend copying your compiled file hex file over to the Pi and using the “update” script to circumvent the total nightmare that is doing anything with serial ports on Windows.
If you go into settings in Arduino, you can turn verbose compile and upload output on to reveal the path where the .hex is saved. This may also tell us more about why it’s failing to upload.