Hi! I understand you signed up for the NYC Transit app free trial, confirmed with Apple Pay, and the app recognizes that, but you keep getting an error message. Let's get this sorted together.

Could you please tell me what the exact error message says? Also, is this happening when you try to activate the subscription, make a purchase, or use another feature? Knowing that will help me provide the best steps.

In the meantime, here are some common things to check with Apple Pay on macOS 10.15.7 that might be causing this:

1. Check Your Payment Method:
Even though the app recognizes your Apple Pay confirmation, sometimes the bank or card issuer may decline the charge. Verify your card details in Apple Wallet and make sure there are no issues with your bank. You can also try removing and re-adding the card.

2. Sign Out and Back In:
Log out from the NYC Transit app, then sign back in. This sometimes refreshes the license status from Apple Pay.

3. Restart Your Mac:
Restarting your device can clear up temporary glitches.

4. Check for App Updates:
Make sure your NYC Transit app is updated to the latest version compatible with macOS 10.15.7.

5. Verify Network Connection:
A stable internet connection is crucial for payment verification.

If you’ve already tried these or the error persists, please let me know the specific error text, and if the payment actually went through or was declined, so we can dig deeper.

Also, occasionally, some users have encountered Apple Pay issues with transit apps due to how the app processes payments or bank declines (Apple Pay itself doesn’t decline payments; the bank does)1 5.

Are you satisfied with this initial guidance? If not, I’m here to assist further.

After I get a message confirming that I have the Pro Free Trial, I get "Sorry, there's a problem."

Thanks for the extra detail! So, you get a confirmation message that you have the Pro Free Trial, but right after that, you see "Sorry, there's a problem." That sounds like the app is recognizing your trial status but then hits an issue activating or fully enabling the trial features.

This kind of error sometimes happens if the app is having trouble syncing your subscription status or loading the trial benefits after confirmation.

Here are some tailored steps to help resolve this on your Mac with OS X 10.15.7:

1. Force Quit and Relaunch the App:
- Click the Apple menu () top-left > Force Quit, select the NYC Transit app, and click Force Quit.
- Then reopen the app to see if the trial features activate properly.

2. Check Your Apple ID Account & Subscriptions:
- Open System Preferences > Apple ID > Media & Purchases, then click Manage to review your active subscriptions.
- Ensure the NYC Transit Pro trial is listed there and active. Sometimes the app shows confirmation but the subscription hasn't fully synced.

3. Clear App Cache/Data:
- Sometimes app data gets stuck; deleting and reinstalling the app is usually a fix, but you mentioned the app detects the trial, so before reinstalling:
- Try deleting the app's cache folder if accessible:
- In Finder, use Go > Go to Folder and enter ~/Library/Containers/ and look for a folder named related to the NYC Transit app and delete it.
- Restart the app afterward.

4. Check for App Updates:
- Make sure the latest version of the NYC Transit app is installed from the Mac App Store. Updates often fix bugs related to subscriptions.

5. Sign out of the App and Apple ID, then Sign Back In:
- Sometimes re-authenticating helps the app sync subscription status properly.

6. Review Network Connection:
- The app needs stable internet to verify trial status, so ensure your internet connection is stable and not blocking app access.

If you've tried some of these already, or the issue persists, this might be a known intermittent issue. I found reports that sometimes after confirming the trial, users get similar errors but after exiting the confirmation screen, the trial still activates properly3.

If nothing helps, I recommend contacting support at [email protected], as they can check your account on the backend. Also, please let me know if you want additional guidance on reinstalling or clearing app data safely!

Are you satisfied with these steps, or shall we try more advanced troubleshooting?