Hello @David L
Thank you for reaching out on the community and telling us about your issue. I do apologize for the issue you're having. I'm wondering why it doesn't update as it sounds like you have it set up update as well. One thing we may be able to try is to copy and validate the file to see if we're able to replicate the issue. You'll be able to find it on the fourth step down below.
https://www.quicken.com/support/advanced-data-file-troubleshooting-correct-problems-quicken-windows
Once you've tried this see if we're able to get your portfolio updated with the OSU. Let us know how it goes!
Thanks,
Quicken Francisco