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Buy nowThanks for joining the Community, AaronBookkeeperer. I appreciate your detailed information and video.
Since steps are being skipped while uploading .QBO files and the transactions aren't being uploaded, but your uploads work while browsing in an incognito window, it's possible this problem's being caused by the browser you're using. Browsers store temporary internet files and sometimes these can cause issues on certain webpages. These types of problems can be fixed by clearing Intuit-specific cookies and cached data.
Here's how to clear Intuit-specific cookies:
Your steps for clearing the browser's cache can be found in our Clear cache and cookies to fix issues article.
I've also included a couple detailed resources about uploading transactions and system requirements for QuickBooks which may come in handy moving forward:
Please feel welcome to send a reply if there's any additional questions. Have a lovely day!