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What's the version of your Outlook? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.
According to the screenshot you provided, since it is blank, I can't be sure what pop-up is. It is suggested that you could try to create a new profile(Control Panel>Mail>Show Profiles>add) and add the account for testing to check if there are some differences.
I cannot locate outlook within control panel to uninstall and install a fresh copy.
We can debug by uninstalling Office via Control Panel > Programs > Programs and Features, as shown in the below figure.
Hope the above help!
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