Once you click the Upgrade button on that message, you’ll see the following error below: The first message that you’ll receive before getting the Outlook can’t upgrade your database error, is a message asking you to please upgrade the Outlook database. If you’ve ever ran into the “can’t upgrade your database error” when launching Outlook, then you may want to give this fix a try. Unfortunately, I ran into a problem when first launching the app. After doing a bit of troubleshooting, and lurking around the app’s bundle, I was finally able to fix the issue. Last night, I decided that I would give the desktop version of Outlook a chance.
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