Hi @tgmis ,
When I reinstalled my office 2016, it was working well. But after updating office, the problem comes back again.
Based on my research and tests on my Outlook 2016 (16.0.5149.1000), the option wouldn't be changed when I close and restart Outlook client, considering it could work well after you reinstall office, the issue may be related to your client itself, so what's the version of your Outlook 2016(File>Office account>About Outlook)? Please first ensure that you have installed the latest update of Outlook client, and have you performed any other operations except updating office before it(such as install any programs or add-ins)?
First of all, in order to avoid the interference of add-ins, we could try to test on safe mode to check if the issue has any difference there(restart your Outlook in safe mode: windows + r , type "Outlook.exe /safe", click enter> modify the option settings>close the Outlook>restart Outlook in safe mode again to check if the option would be changed).
If the issue could be reproduced in safe mode, considering corrupted outlook profile may cause it, it's suggested to create a new Outlook profile and readd your account for testing(Control Panel>Mail>show profiles>Add>Readd your account).
If the issue still exists, it may also be caused by corrupted Outlook client, please try to repair your Outlook to check.
If your issue has any update, please feel free to post back.
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