Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello Jesslyn,
No need at all, indeed.
In OGCS, go to the Settings tab, and see that there are two sub-tabs in fact: "Sync Settings" and "Application Behaviour".
Open the second tab, where the first checkbox parameter is "Start on login". You can even adjust a number of seconds after login to launch the app, to unencumber the login launches sequence (I use 10 s).
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Do not forget to then click on the "Save" button, lower right of the page.
Cheers,
H.-P.