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We are moving to a third party help desk supplier (@thirdparty.com) while keeping the internal email address helpme@mycompany.com. We both use Exchange

We will add an exchange rule to forward all emails to helpme@mycompany.com to helpthecustomer@thirdparty.com meaning everyone internally will still see the old address.

Management want all return emails from the help desk email helpthecustomer@thirdparty.com to look like they actually come from helpme@mycompany.com

I don't want to change the email address of the return email, just to header, so it looks like it came from helpme@mycompany.com

I've read countless Exchange documentation but can't find anywhere that will allow me to do it. Can anyone help, is this even possible?

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Based on your question it looks like you are missing some email routing knowledge, so this answer might be somewhat longer.

When an email is send out, the email server which send out the email is responsible for adding the "reply to address". So if you forward emails to the 3rd party company, and they send out answers, they are responsible to creating the correct "reply to address". So they might use helpme@mycompany.com when they send out the answer and need to configure it in there environment. BUT if you use antispam technicians like SPF (or DKIM, but I think based on your posting only SPF might be used. So DKIM is only added for completeness) you need fully allow the remote company to send emails in your name, that means you need to add there mail servers to your SPF record. Some companies do that, some others do not really like the idea that a remote company can send all kind of emails in there name. Its mostly up to your management. For some companies this is also a legal question (who is archiving the send emails if something happen and you need a proof what was send / done when).

I also wouldn´t give the remote company so much power that it would be hard to leave them. I would give them access to your Exchange server and they can work with an shared mailbox directly on your server to send out emails (e.g. via OWA). If they use a 3rd party HelpDesk troubleshooting system (e.g. Vera, OTRS, ...) then you might come up with a POP3 or IMAP implementation. Then the remote company can deal with the emails but you still have full control over the connection and if something happen, you still can pull the plug.

Side note: Every email has a so called email header, and every user is able to check that. Inside the header you can see the servers which where used to send the email. So skilled persons are still able to see that the email wasn´t send via your mailserver.

But if you really need to rewrite an incoming email address, you can implement an Microsoft Exchange Edge server and use Address rewriting (start here). Microsoft described it as:

Address rewriting in Exchange Server 2016 modifies the email addresses of senders and recipients in messages that enter [...] your organization through an Edge Transport server. [...] The primary reason for address rewriting on inbound messages is to deliver messages to the correct recipient. The address rewrite entry, which you create, specifies the internal addresses (the email addresses you want to change) and the external addresses (the final email addresses you want). [...] You can create address writing entries for a single user (chris@contoso.com to support@contoso.com), a single domain (contoso.com to fabrikam.com), or for multiple subdomains with exceptions (*.fabrikam.com to contoso.com, except legal.fabrikam.com).

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  • You are welcome. Please choose the correct community (ServerFault) the next time for admin questions, so that we do not need to migrate the question :-).
    – BastianW
    Sep 6, 2017 at 21:11

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