So the issue isn’t that mail’s aren’t getting *delivered*, it’s that they’re not being triggered?
If so, this likely points to an order status issue than a strict emailing issue. Order status change issue are usually the result of IPN notifications from a payment gateway not getting through, and therefore the order status changes never occur. To test for that, check the order notes in **WooCommerce > Orders > YOUR ORDER > Order Notes** – it should say something along the lines of order status changes from x to y (Note: not the manual order change initiated by store admin, it should be by the payment gateway).
If you’re not seeing that, it likely points to a payment gateway setup failure or server side error.