Debug stops attaching, only fixed with a system restart

[rubybrowncoat]

I'm on Windows.
The debug works fine for a while but at some point it stops attaching. (Pretty randomly thus far, once it was after I put the system to sleep and woke it back up a few hours later)

The tasks are executed correctly and the simulator is launched but the debugger can't attach to it and fails.

 *  Executing task: Playdate: Build 

Compiling...
> "~\PlaydateSDK\bin\pdc" -sdkpath "~\PlaydateSDK" "~\project\source" "~\project\Project.pdx"
 *  Terminal will be reused by tasks, press any key to close it. 

 *  Executing task: Playdate: Run 

Checking for running Playdate Simulator...
> tasklist
Starting Playdate Simulator...
> "~\PlaydateSDK\bin\PlaydateSimulator.exe" "~\project\Project.pdx"
 *  Terminal will be reused by tasks, press any key to close it. 

One difference I found is that when the debugger works you can keep the simulator open and it replaces the build on the fly before attaching to the process, but once it stops attaching it also stops replacing it, so the first time it runs the simulator and starts the project (but doesn't attach) and subsequent launches (task Playdate: Run) don't do anything at all unless you close the simulator.

There error I get doesn't say much.