Auto-Send News to Kindle

Hi-- I recently had to set up Calibre on a new computer. Although "Automatically Send Downloaded News to E-Book Reader" is checked and, under Sharing Books By Email "Auto Send" box also is checked, Calibre is not automatically emailing the news downloads to my Kindle. If I manually click the Connect/share button I can have Calibre send by email, but I really need this to happen automatically.

Assume I am missing a setting somewhere. Can someone help?

Thank you as always!