That is… not really the proper way to sideload games om the PlayDate.
- Rename the extracted game folder to octo-crank-playdate.pdx
- Zip that folder, so you get a octo-crank-playdate.pdx.zip
- Just upload it onto your Playdate via https://play.date/account/sideload/
Yes, you could still manually boot into Data Disk mode and manually do that yourself, but I don’t see why you couldn’t just upload updates the same way, except for a mistake in the buildID file. Even in that case, yoi could just delete the previous game in the sideload web page. The website tracks the different version you’ve uploaded.