Hi iwelch42,
Thank you for reaching Microsoft Community.
To make sure: is this the handwriting window you're using? If not, please try to take a screenshot of the handwriting window and share it with us here.
Please go to Windows Settings > Devices > Pen & Windows Ink. Check if the Show handwriting panel when not in tablet mode and there's no keyboard attached option is On. Turn it On if it is Off.
Try also to Touch Keyboard and Handwriting Panel Service is set to Automatic in Services. Press Windows key + R. Type services.msc then click OK. On the Services window, locate Touch Keyboard and Handwriting Panel Service. Right-click on it and select Properties. Under the General tab, Confirm if the Startup type is set to Automatic. If it is already on Automatic, close the Properties window then right-click on the Touch Keyboard and Handwriting Panel Service then select Stop. Once the service is stopped, right-click then select Start to restart the service. Close Services window then test the functionality again.