If you are having trouble sending secure emails in Outlook via Govern add in, it may be due to a temporary issue where Outlook is unable to properly apply security policies. Please refer to the below screenshot, where clicking Send may sometimes cause the message to load indefinitely, showing "Secure Email is working on your request." This is usually due to corrupted local cache files. Clearing the cache typically resolves the issue quickly.

How to Fix It: For Mac Users
Close Microsoft Outlook and open the Terminal app
Copy and paste the following commands, then press Enter:
rm -rf ~/Library/Containers/com.microsoft.Outlook/Data/Library/Caches/*
rm -rf ~/Library/Containers/com.microsoft.Outlook/Data/Library/WebKit/*How to Fix It: For Windows Users
Close Microsoft Outlook and open the Command Prompt app
Copy and paste the following commands, then press Enter:
cmd /c rd /s /q "%LOCALAPPDATA%\Microsoft\Office\16.0\Wef"Still not working?
If the issue persists, please contact us at Help Page and share additional details such as:
Screenshots of the error
The exact error message or code displayed
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