How can I originate emails to recipients NOT listed in email headers (using EWS or office-js, or maybe emulating SMTP using the MS stack)?

Question

My add-in does "forensic mailing" (all email recipients receive imperceptibly different steganographic mail body content) for the purpose of identifying policy infractions (e.g. "leaks"). e.g. This means that when an email is sent:-

From: Person A
To: person B 
Cc: person C
Bcc: person D

that 4 different individual emails are generated (the original in the senders "Sent" folder, plus a new version for each of the 3 recipients = 4 total).

Using SMTP, it's a simple matter to set the appropriate headers, and use "RCPT TO" 3 times to send each mail.

What would be the Office-JS or EWS or any other available equivalent way to originate my emails using "Microsoft Techniques" ? Is it possible to perform "SMTP over EWS" or similar, so I can re-use my existing (Linux) codebase ?

Is there some way to specify a "Bcc" recipient, along with the "To:" and "Cc:" email headers, and then transmit the mail to that Bcc recipient only, to emulate SMTP ?

Answer 1

No, unlike SMTP, EWS, Extended MAPI, and Outlook Object Model won't let you specify different recipients than those that will actually receive the message.

SMTP is your best and only option in this case.