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We are sending an email to a journaling mail box using Redemption. We wish to send an email with a To address that's not the address the email is sent to.

For example: Create an email with the To address set to jbloggs[at]example.com but send it to TomJones[at]test.com so the email arrives in the TomJones[at]test.com mailbox with the email To address set as jbloggs[at]example.com

I know this sounds like spoofing, but it's a requirement we got from a client that we need help with. We've seen other companies able to do this.

UPDATE

Just found this article after reading @i486 reply: In SMTP, must the RCPT TO: and TO: match?

How do you set / edit the SMTP RCPT TO value using Redemption in C#?

Eugene Astafiev
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m_collard
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  • Using a name? To: `"jbloggs[at]example.com"`. – CodeCaster Apr 28 '23 at 10:18
  • Theoretically it is possible. `To` address is line in headers. And the actual recipient address is `RCPT TO` line in SMTP. But there is a risk to be ignored as spam. – i486 Apr 28 '23 at 10:29
  • You can use BCC to add multiple hidden emailaddresses (like jbloggs[at]example.com) and the To-address is jbloggs[at]example.com – Chris Berlin Apr 28 '23 at 10:57

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You cannot do that through Outlook Object Model or Extended MAPI - the recipients you specify on a message are those who will actually receive them. The only exception is the appointments - OOM specifies non-sendable recipients and stores them in a blob, while the recipient table only has the recipients who will actually receive a meeting. But that is just an eye candy.

SMTP is the only way (as @i486 noted in the comments) - the recipients who will actually receive a message are specified in the "RCPT TO" SMTP command, but what an email client will show is what is in the message envelope in the To/CC MIME headers, but they are not used by an SMTP server.

Of course you can create a message that looks like it was received (with the fake recipients and received time) directly in the target mailbox, but you'd need to be able to connect to that mailbox directly.

Dmitry Streblechenko
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