Actually, It is the default functionality of WooCommerce and a little tricky one as well, let me try to explain it to you in detail.
1. The Order is not showing in Order Tab on my account page when adding the order to the cart, so the order only shows in the Order Tab on my account page when you will confirm and complete the order, until and unless, you will not complete the Order, it will stay in the Cart and Checkout, It will move to the Order Tab on my account page after the completion from the Customer. This is how it works.
2. Customer/User details automatically fill on the Checkout page when adding the product to the Cart and then move to the Checkout page, so this is also not possible as there is no such option in the WooCommerce for it, and it requires some extra Customization.
But when the user adds the product to the cart and then moves to the checkout page and fills all the fields properly and completes the order, and then moves to the shop page to purchase another product, and add the second product to the cart and then move to checkout, now for the second time the customer details will be there on the checkout page which the customer added for the first item. This is how it works.
I have captured the videos for you, please watch them here:
Regards 8Themes Team.
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