Hi George Holod,
If Outlook does not appear under Startup apps, you can try adding its shortcut manually. Depending on your version, Outlook may also appear as Outlook (classic).
Please try these quick checks:
- Press Windows key + R, enter
%ProgramData%\Microsoft\Windows\Start Menu\Programsand press Enter. - Look for Outlook or Outlook (classic).
- If the Outlook shortcut is missing, try an Office Quick Repair from Control Panel > Programs > Programs and Features > Microsoft Office/Microsoft 365 > Change > Quick Repair.
I hope this helps you get Outlook launching normally with Windows. Let me know if you need further assistance, feel free to ask me by clicking "Add Comment" or "Add Answer" if you cannot add comment so your response will be visible. Thanks for your effort.