It always errors out the first time, then the teller resets the transaction, I scan again, and it works. I always assumed it was due to an issue with the card readers.
I'm going to head to the grocery store and do a small purchase to double check, but it looks like my Jan 2018 phone might be NFC hooped?
I'll chat with Apple customer service and see if they are willing to fix it if that is the case.
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Update: Talked with Apple Support. I brought up the issue, and they asked why I was discussing this. So I shared the link. They pored over it for a while and asked me to wait a few minutes multiple times (likely showing a manager or tech rep).
They then asked for my serial number and iOS version to confirm I was on the latest iOS (I am).
After asking to wait another few minutes, they asked me to do a General > Reset > Reset All Settings. This removes my Apple Pay Cards. So I'll need to re-add them and then try a purchase again at some point.
Following that, they sent me an e-mail with some help articles and have asked me to proceed through the following if it still doesn't work:
- Redo the General > Reset > Reset All Settings
- Reset Network Settings
- Perform a full Factory Reset (Wipes device)
I'll proceed with the rigamarole and see if it actually fixes anything. To be honest, I wager I'm still going to keep seeing issues and have to eventually be a little pushy and have the device replaced.