Arduino IDE not detecting Uno when shield attached

So when I have the sm130 Evaluation shield attached, the IDE doesn't recognize the Arduino. When I open System Information (OS X on a 2015 MacBook Pro 15), the device is recognized as "USB2.0-Serial", however, the IDE doesn't acknowledge it.

On the desktop PC, the Uno is recognized, but will only upload 85%, and if I trickily press the reset button and then click upload with Just the right timing, Arduino receives the sketch.

The problem does not occur when the shield is not attached, but I have one module with the shield soldered in (to accommodate for a low-profile installation).

Something tells me there has to be a way to short out two pins or something to make the board think there's no shield attached.

So I bootcamped into Windows 10 and it successfully uploads.

After a few more tries, it failed, and working my reset button magic, it eventually will work, but there has to be some way around this or some soft of a fix.