Can you look how things look in your send folder ?

Are you using exchange to send (as the to hearder might be added by the
smtp server).

So you want :
1) a warning when To: header is empty 
2) something else ?

I'm not sure about 2.

I'm also not sure having an empty TO: field is illegal. According to
http://tools.ietf.org/html/rfc2822#section-3.6 te To: field is even
optional.

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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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