My suggestion is to add a dialog when the user clicks send (validating
the mail) that warns about an empty To: field that this may cause issues
for some MTA and/or email clients.  This dialog could also suggest
adding the sender as the recipient of the To: field.  The dialog could
then have three buttons: Cancel, Send with sender as recipient, Send.
Default being Send with sender as recipient.

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https://bugs.launchpad.net/bugs/702097

Title:
  Some versions of Outlook misinterpret mails with only BCC recipients

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