A few days ago, I tried plugging a Chargepoint charger into the Clarity. I encountered a lot of resistance halfway through the insertion and was not able to push the charger all the way through to the 'click'.
Sometimes stuff gets jammed in the charge handle or port that prevents full connection. In cold weather ice has been known to be an issue.
If your car works fine with other EVSE's, it is likely an issue with the chargepoint. I've occasionally encounters nozzles that were a very tight fit and hard to fully engage, but if it hits a sudden stop it is likely something in the handle.