I have done this successfully in the past using my mac. I used the IBPY package. However, I recently started using a Windows VPS so that I can make trades at any time during the day regardless if my computer is on or not. When transferring the code over to the VPS, it didn't seem to work. I've already followed guides to setup TWS (enable socket clients, add trusted IP, etc.). In my troubleshooting, I ended up pressing the button "reset order_id configuration." Which seemed to compound the issue. The end goal here would be to be able to make a trade using my VPS, the rest I can handle. I recommend using TeamViewer for this project.