Sent email conversation view on multiple outlook clients for same email address

Hello,

Having an issue with Outlook 365 on Mac. We have 2 Macbooks both using the same email address info@. When you send a reply on the one Macbook you can see the conversation reply in the same thread. like below:

However, on the other Mac you can't see the sent email conversation in the same thread, the message saying  “You have replied to this message on ....” does not appear which makes it very difficult to know if either of us working on the mailbox has replied or not.

How do we get it to display the replies on both devices in conversation view so we don't end up replying twice. Conversation view is enabled.

Please help!

Wesley

P.S. image just for reference.