Hi Scott,
From my initial understanding, I can see two issues over here.
1. Reverse Path Failure
2. Asymmetric Routing
If you can confirm that traffic is reaching the server using the /23 public ip, then issue 1 is not being encountered.
The asymmetric routing issue, can be solved by enabling tcp-state-bypass until the subnet transition takes place.
You can go through the following link for more details on asymmetric routing and how to mitigate it:
https://supportforums.cisco.com/docs/DOC-14491
I hope this helps.
-Shrikant