OK, check and try this.
With your LEFT KEY notch, facing to the right, as you would insert it, bend the tip DOWN a smidge. Just a fine arc should do it, not a fold or anything, just a smooth curve so the tip is not pointing up. and insert the tool like you are trying to point it down.
I bent my tools up and down, down it worked, up and it would not insert like you described.
I have these tools and when I use the long angled option, I can release it from the radio by pushing the handle of the tool away from the center of the radio, as in on the right tool, push your hand towards the right, try to rotate the tool counter clockwise when looking straight down on it. But if your tool is like the shorter rounded slope, that clicks in solid, and I can't get it to release without pushing the hidden tab.