How can I originate emails to recipients NOT listed in email headers (e.g. like how SMTP works)?

Chris Drake 96 Reputation points
2021-08-21T22:38:04.023+00:00

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 (in 3 different sessions) to send each mail.

What would be the equivalent or any other available 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 ?

e.g. 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 ?

Office Development
Office Development
Office: A suite of Microsoft productivity software that supports common business tasks, including word processing, email, presentations, and data management and analysis.Development: The process of researching, productizing, and refining new or existing technologies.
3,484 questions
Exchange Server Development
Exchange Server Development
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Development: The process of researching, productizing, and refining new or existing technologies.
507 questions
Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
7,347 questions
{count} votes