Thank you for taking the time to visit the Community to post your issue, although I apologize that you haven't received a response.
At this time I would recommend contacting support directly for advanced troubleshooting steps.
https://www.quicken.com/support#contact-support
Quicken Care has the tools to review the logs and escalate the issue if necessary.
Thank you, -Quicken Tyka
Hello @drewbp
Thank you for reaching out on the community and telling us about your issue. I do apologize in the issue you're having. That is odd I'm wondering where exactly the issue is. I believe in this case it might help trying to see on a test file if we have a similar issue. This will give us a better idea of where exactly the issue is. I'll leave steps down below and you can find it on the third step on the article.
https://www.quicken.com/support/advanced-data-file-troubleshooting-correct-problems-quicken-windows
Once you get the chance let us know what you're able to find out. From there we'll see what we able to find next.
Thanks,
Quicken Francisco