Make sure the Addin in showing
For CloudFiler to be able to file your emails it needs to be visible. If it’s not showing, your emails won’t be filed.
Make sure it's active
If it’s not already showing to the right of Outlook, click on the CloudFiler icon in the ribbon menu

Now pin it to ensure that it does on disappear

In Classic Outlook you can re-size it to make it narrower, but in New Outlook it is given a fixed width by Microsoft
Next step: Ensuring there is a TESTING filing location