Hello Ben,
Thank you for contacting the PureCloud Community with your question. I will be glad to help.
Looking at the timeline images, I can tell you there is definitely a callback that is being scheduled. What I can't tell is how this call is originating. So your question about it never reaching an agent is a good one and I am not sure of the answer. Some mechanism is scheduling a callback for a specific date/time and then presenting that to an agent which is expected behavior.
I would be curious to know the details of the call and the best way for our teams to troubleshoot this would be by looking at a conversation ID. If you can open a ticket with our Support team, they can dig into the conversation example(s) you provide and find out exactly what is going on.
Here is the Resource Center page that outlines contacting PureCloud Customer Care.
https://help.mypurecloud.com/articles/contact-purecloud-care/
You will want to use the My Support Web Portal which is linked on that page.
Thank you,
Chad