Should Not Need to Tag Emails From Sent Folder When Sending From Case Docs

When I email a document from Case Docs and open the email in Outlook, I cannot then tag that email from the Outlook tab. I click on tag, and then it greys out. Even when I send the email, it will not tag. My workaround is to go into my Drafts folder and tag it there. However, this does not tag the email that I send, it tags it as if it was sent directly from Case Docs. I then have to go into my Sent folder and tag the email there so the body and correct subject line are listed.

It did not used to be this way. The tag from the Outlook tab that popped out worked fine; I went out for a few months; and now it does not work like it used to. Results in an unnecessary waste of time.