Try to launch Classic Outlook Directly Using the EXE. Sometimes the New Outlook hijacks the shortcuts. Try launching classic Outlook manually: Press Windows + R Paste this path and press Enter: ... or for older installs: ... If Classic Outlook opens normally, re-pin it to the taskbar and stop using the New Outlook shortcut. See if this helps.
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From classic Outlook, turn on Try the new Outlook once so both apps are available. Then toggle back to classic as above. Pin both Outlook (classic) and new Outlook icons to the taskbar or Start for easy access. Mail, calendar, and folders in Exchange/Outlook.com accounts remain intact; reverting only changes which client is used to access them.