Retention Policy Mail Tip Not Showing

We are using Purview for mail retention. We have an auto-apply label policy that will assign a label (called Pre-Retention Policy Label) to all mail sent or received prior to January 1, 2024. Users may override the auto-apply label with a manually applied label of 6-months, 5-years, or 10-years. All of these show a Retention mail-tip on the item by default. 

This all worked great until we deployed a Default Retention Policy that will delete mail after 2 years. All new and previously unlabeled mail is getting this label and all of the mail-tips are still showing up as excpected. EXCEPT for mail that has been labeled by the auto-apply label policy. No mail-tip shows up for these items.

I can confirm that the auto-apply label is being applied correctly. To do so, I ran an eDiscovery so that I could see the Compliance Label on a given item was correct based on the auto-apply policy vs the Default Retention Policy.

Does anybody have any clue why the Mail Tip wouldn't be showing for my auto-applied label?