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Hi There. I am Bing and I look forward to helping you with your issue today.
Could you please advise your Outlook version? What's your email provider? Ever tried with other mailboxes?
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Okay, I just leave some homework for you before signing off. :)
Please start Console app then keep it running in the background and better on another screen. Choose All Messages in left pane and scroll down to the last item in the right pane. Then start Outlook and carefully observe if any error reported by Outlook. Please let me know your findings. Thanks.