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How do I connect point A to point Z? Currently, when I select Anchor point A, it tries to connect point A & B (as you can see in image 2).

image 1

Image 2

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You should select both shapes and go to menu: Layer -> Paths -> Join

enter image description here

And two shapes will be joined.

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    So you can't actually choose what anchor points join? It automatically assumes you want to join the closest points. – Sam Bazalo Jul 12 '16 at 0:20

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