The first thing I noticed the trailer tires did not have chocks.
I am sure the trailer was high hitched thus the hitch did not latch. This was most likely because of the extra lube plate.
The first picture shows what the release handle should look like when the hitch is latched.
The second shows it after connected to the trailer. You can clearly see that the hitch is not latched.
In the third picture I can still see the hitch pin as the hitch jaw has not completely surrounded the pin and locked in place.


