An option to automatically reboot to Drive mode when the simulator makes a PlaydateSerialWriteLine request

Development on real hardware would go a bit faster if I didn't have to manually reboot to Drive mode to upload the pdx folder from the simulator, and if the simulator/hardware did it for me

The Simulator will already do this for you. Run your game then choose Upload Game to Device.

On Mac, at least, this will reboot the Playdate into disk mode, copy the .pdx, reboot the Playdate back to system, and finally run the .pdx.

There's also an option to Boot to Data Disk for times you need to do that.

https://sdk.play.date/inside-playdate/#_using_your_playdate_to_control_the_simulator

This functionality does not appear to work on Windows.

I have my PD connected on the lock screen and the menu is disabled
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If I exit the game to the menu, then I can click upload, and I get this (and it takes about 5 minutes for it to go away)
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I am asking for this functionality to be completely automatic and require no intervention on the Playdate side, similar to how Android development works.

The boot to drive data disk option is even disabled, and use device as controller does nothing

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These features won't work while the Playdate is on the lock screen. Do you see different results when you unlock the device first?

the first screenshot was at the lockscreen, everything else was unlocked. Though I'd like it to work while locked too (and then unlock, and open the game if it came from the dev environment so that you can keep installing multiple games at once), zero intervention necessary.

You have to be running a 3rd party game for this menu item to enable. Then it works as you'd expect.

Anytime I'm in the simulator would be in a third part game though.

Not exactly, for example, it won't be enabled for system apps such as Settings. Also, you have to be in the game, not just in the launcher.

I meant anytime I am in the simulator, I am in a third party game. I am never in the launcher/settings app.

OK, in that case the device needs to be unlocked and the menu will enable. Edit: Also, the serial connection to the device needs to be active. You can check your Console log for any serial command errors. The serial connection is usually made automatically when the device is unlocked and stays active as long as the device isn't locked or put into disk mode.