Hi @wweaver,
If you look in woocommerce/includes/emails/class-wc-email-new-order.php
there are the following hooks that are initiated.
add_action( 'woocommerce_order_status_pending_to_processing_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_pending_to_completed_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_pending_to_on-hold_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_failed_to_processing_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_failed_to_completed_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_failed_to_on-hold_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_cancelled_to_processing_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_cancelled_to_completed_notification', array( $this, 'trigger' ), 10, 2 );
add_action( 'woocommerce_order_status_cancelled_to_on-hold_notification', array( $this, 'trigger' ), 10, 2 );
When the order status goes from failed to processing or failed to completed the email should go out to the admin. The Braintree plugin correctly updates the status from cancelled to processing/completed. It sounds like you either have a 3rd party plugin that’s unhooking this email or preventing it from going out.
Kind Regards,