Tim, go ahead and remove this post if it’s not appropriate. But in an attempt to help others with this issue, I must say I managed to find a different SMTP plugin that works with Woocommerce. The name of that plugin is “Mail Integration for Office 365/Outlook”
Has there been any progress on the Woocommerce issue? I’m just finishing a big e-store move and ran into this. Oddly enough I can not get our Office 365 setup to work with authenticated SMTP. It keeps giving me an error : “network is unreachable”
Using the O365 API I’m getting no issues with any other e-mails on the site, except for the ones sent by Woocommerce.