How Can I Automatically Attach Emails I Send From Outlook?

While there is no way to automatically add sent emails, there is a similar dialogue box which can be prompted when send is pressed on an email to the dialogue box seen when attaching an incoming email.

To enable this feature, simply start a new email in Outlook and press the SmartAdvocate button at the top of the screen.

Check the box next to Add to SmartAdvocate and by default the dialogue box to attach the email when appear when an email is sent!