This is gonna change my life. WooCommerce 10.9 is adding core logging of transactional emails; you'll see sent emails, failed ones and all the statuses in the admin now.
http://developer.woocommerce.com/2026/06/03/transactional-email-logging/
This means weekly guessing games (like the dog harness shop every monday getting thier order email) are history.
Please don't assume delivered from this log either, A sent status only indicates that the email left the shop.
Deliverability of the email after that isn't shown. The only thing we get is the failure part at a glance now.
This is the first thing Im going to check on client shops once 10.9 lands!
https://developer.woocommerce.com/2026/06/03/transactional-email-logging/