I am having to continuously login to the FYI Add-in when using Outlook, or Office. This is regardless of whether the FYI Drawer is pinned or not.
This may be caused by your browser clearing your cookies automatically.
Check the help for the browser you are using. You can search for something like "chrome clearing cookies automatically" For example, the following is the Chrome help which gives the details for Chrome https://support.google.com/chrome/thread/2125707?hl=en