I was told on case # 8010388828 that Attach to Act will not "find" the "To" Contact like it does from all other folders in Outlook because it is "DESIGNED" to look in the "From" box. It also will not Quick Attach to the "To" Contact as well.
This seems to be counter intuitive and does not make any sense. I tested it with the support person and that is what it does. It will let you look for the contact and then you can attach it.
In the other folders it seems to work fine in that it grabs the To contact and puts it in the right panel for you.