Let's make sure that your transactions are downloaded in your account, stephenbarker.
I just want to ask if you can share with us what happens every time you update the bank? Can you also tell us the name of the bank that's connected in QBO?
In the meantime, let me share some steps to check if this is caused by a browser-related and issue. These steps can resolve online banking issues as well.
Update the account in a private or incognito browsing session. Follow these keyboard shortcuts depending on the browser that you're using:
CTRL + Shift + N for Chrome
CTRL + SHIFT + P for Mozilla
Go to File, then click New Private Window if you're using Safari.