Outlook and Transactional emails

Hello! I have been working with Brevo for quite awhile and lately I have noticed emails are not being sent to outlook / office 365 accounts (but it works with gmail and other email software).

Details
Wordpress site with subscription based membership for a non-profit sprort advocacy group
Paid Membership Pro handles the membership transactions
Brevo handles all transactional emails
WP Mail Logging set up to track emails sent

If I force reset password, send test emails via the Brevo plugin, or update subscriptions, emails do send to outlook/office 365 clients, but they are in the WP Mail Logging tracker. If I replicate everything with a gmail account, it works immediately. Kind of a big issue for me alone who has their email set up with office 365, because I can’t be copied on transactions, but also I am sure some of my clients use outlook / office 365 as well.

Is there anything I am missing for this email software?