Hi slumberchi,
From what you described in your original post, here is what we recommend: Use Express Mode with transit cards, passes, and keys in Apple Wallet.
Next, we'd like to show you how to perform the recommended troubleshooting steps via the link above. Please click to open the link, then read through the steps in the section titled "How to use Express Mode on your iPhone or Apple Watch."
1) Hold the top of your iPhone or the display of your Apple Watch near the contactless reader.
2) When the transaction is successful, a checkmark and Done appear on your device. If you're riding transit, the terminal gate opens and might beep.
And that's it—no need to wake or unlock your device, or authenticate with Face ID, Touch ID, or your passcode, or open the Wallet app.
The reason why we are recommending the steps above is because they will show you how to use Express Mode with transit cards.
If you're still experiencing the same issue, we recommend that you contact Apple Support directly so that they can work with you to find a solution.
Contact - Official Apple Support
Thank you for participating in the Apple Support Communities.
Cheers!