@soren OK, So despite the no project, I tried uploading and it behaves really strange. It says "Connected" above the console despite the console saying "Connecting on COM4..." at the same time.. how does that make any sense? Here's a snippet of my log: Uploading project (main folder)... Reading file status Failed to connect (Error: Writing to COM port (GetOverlappedResult): Operation aborted). Click here to try again. Failed to read project status, uploading all files [1/5] Writing file boot.py Connecting on COM4... ** and here it will stay forever, while at the same time displaying "Connected".....