Custom shape etch - How to attach to pins

Hello,

I'm trying to copy this design:

And I'm wondering what is the best way to go about creating the highlighted shape that is the trace etch. 

Here is my attempt:

Obviously, my attempt is very basic but it shows how one attaches and the other does not. 

1) Why does one of my shapes not connect?

2) What is the best way to go about creating these shapes?

Cheers,

Fraser