[THIS SOLUTION IS STILL IN PROGRESS]

When doing an email merge from Word to Outlook in Office 2011, the generated messages are moved to the Outlook "Drafts" folder, rather than "Outbox." There is no way to send all of the messages in the Drafts folder with one click; they must be opened and sent individually.

Here is a workaround using an Automator script to create an action that sends all of the selected messages in your Drafts folder:

  1. Download the attached Automator script.
  2. Do your email merge to create outgoing messages in your Outlook drafts folder.
  3. Go to the Drafts folder and select all messages that you would like to send.
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