While these small uninsulated terminals are not technically D-Sub style I have found they perform best when crimped with a D-Sub crimp tool. Over the years I have tested these small terminals with piles of crimp tools and found the D-Sub style dies do the best job of any tool I have used.
To crimp these rings Insert with the seam facing the "butt cheek" dimple. I have done it both ways and this way holds best and the wire breaks before the crimp lets go.