I've been having issues getting my Playdate to be recognized by the simulator for some time now, which is now resulting in me being unable to do anything with my development unit. This is on Windows 7 using the most up-to-date SDK and with my Playdate also up to date. When I have the Playdate connected to my PC and I'm in the home menu, the Playdate Simulator's Device dropdown will all be greyed out. In addition, when I look in my device manager, it says that the Playdate's drivers have not been installed.
I'm able to do a work-around where I boot into a Linux virtual machine with the SDK installed and then the simulator within Linux recognizes my Playdate and allows me to turn on data disk mode, causing Windows to see my device. I'm then able to get pdx files onto my device while the Playdate is in this data disk connection. But otherwise, Windows never sees the device (at least as far as I've been able to tell).
I don't know the solution yet as to why Windows isn't recognizing your Playdate, but if it helps, I can tell you that a shortcut to putting your Playdate into Data Disk mode is to hold LOCK + MENU + D-pad LEFT for about five seconds.
To take it out of Data Disk mode, just push the A button.
Welp, looks like that shortcut does work for me fine. It seems I just needed any way to trigger data disk mode for Windows to see the Playdate. Had no clue there was a shortcut to get into that mode. .-.
Still, yeah, don't know why Windows doesn't recognize the Playdate otherwise (or if anyone else will run into this problem), but this does pretty much fix my use case for my unit.
While the Simulator works on Windows 7, we aren't officially supporting since it's no longer supported by Microsoft and is rather old at this point. The Playdate requires a CDC driver to mount which isn't included by default in Windows 7.