Hi, Jeff Ranck!
Thanks for reaching out to Microsoft Community. We are sorry to learn you have issues allowing your Surface Dock 2 to display the external monitors connected to it. Thanks for taking the time to let us know about this and allowing us to help you out.
May we know if tried a direct connection to the Surface Pro 7's USB-C port to check if the monitor will be recognized?
Also, have you plugged the USB-C cable to the ports at the back? Those USB-C ports near the audio jack.
If it will not work, you may need a USB-C to HDMI adapter to plug to the dock to plug HDMI the cable of your monitor (if using the HDMI port of your monitor).
For further steps, you can be guided at https://support.microsoft.com/help/4023496/
If this answers your question, please let our Community know by marking this post as an answer. Otherwise, don't hesitate to respond to this thread if there’s anything else that needs to be addressed.
Kind regards,
Janette_Z