Hey there, @LaurenBurgess.

Thank you for sharing the troubleshooting steps that you've made to address the issue.

Since clearing the cache doesn't remove the error message, I'd recommend using another supported browser. This way, we can check if there's a problem with your current browser.

Let's also make sure that you're using the latest Adobe Reader/Acrobat when uploading the PDF file.

If you're still getting a similar result, please contact our QuickBooks Support Team. They have the available tools that could check your account and verify the cause of this issue. 

Here's how you can reach out to them:

1. Click the Help menu in the upper-right hand corner and click Talk to a human.
2. Type in "Talk to a human", then press Enter.
3. Look for I still need a human and click on it.
4. Select Get help from a human.
5. Choose between Chat with us, Schedule an appointment, or Have us call you.

You can also view our support hours to ensure that we address your concerns on time.

Let me know how it goes by adding a comment below. I'm more than happy to lend a helping hand. Keep safe!