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Stop Monitoring this Add In
Go to File
Click on the Manage COM Add-Ins button
Scroll down to your Wise Owl Outlook Helper and choose the option to not monitor the add in for 30 days and then click apply.
Close Outlook and restart it to have your changes take effect
Always Enable this Add In
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You can tell that Outlook has disabled the Add In if you see the yellow bar at the top telling you about an Add In problem.
Click on the View Disabled Add-Ins button (or use steps 1 – 2 above to locate your app in the Add Ins section)
Open the options under the Add-In heading that was disabled and click Always Enable and Apply
Close Outlook and restart it to have your changes take effect
Unfortunately, Outlook does not offer an option to mark an Add In onto the ‘Always Enable’ list proactively – It can only be done in response to it being de-activated.