I understand that the Print Later status remains persistent even after the item has been printed, FeeGarro. We can utilize the Verify Rebuild and Repair tools to address the issue.

Corrupted files in QuickBooks can disrupt processes like updating transaction statuses or marking printed invoices as cleared. Similarly, a printing queue glitch can cause the Print Later queue to stop processing or clearing transactions properly.

With that, we can use the Verify tool to identify common issues within a company file. Then, rebuilding data often resolves glitches preventing the transaction status from updating properly.

Here's how to verify:

1. Go to Window, then select Close All.
2. Go to File, then choose Utilities.
3. Select Verify Data. If you see:

To rebuild the data in your company file, please follow the steps provided below:

1. Go to the File. Then select Utilities.
2. Click on Rebuild Data.
3. Follow the on-screen instructions, then press OK.
4. Select the place where you want your backup file to be saved, then tap OK.
5. Enter a new name in the File name. Click Save.

If the issue remains, I suggest closing your QuickBooks Desktop and downloading the QuickBooks Tool Hub. Proceed to the steps below: 

1. Open the downloaded file (QuickBooksToolHub.exe).
2. Follow the on-screen steps to install.
3. After that, open the tool hub on your Windows desktop.
4. Select Program Problems.
5. Click Quick Fix My Program.
6. Start QuickBooks Desktop and open your data file.

You can also refer to this article for more detailed information and additional troubleshooting steps. Repair your QuickBooks Desktop for Windows.

We can also create and send customer statements to provide them with an overview of their invoices, payments, credits, and account balances.

We're always available to help you out if you have any other concerns with QuickBooks Desktop.