Background: I work at a company with several confidential business partnerships that require employees to appear as though they work for another company/brand and use multiple domains via email in accordance with whatever brand they happen to be representing at the time. We've had moderate success with most of this requirement so far. (I have an Exchange 2013 on-premises DAG environment in a one forest, one domain architecture, but multiple SMTP domains)

Problem: When a user sets up an out-of-office to reply externally, Exchange auto-replies only from the primary SMTP address of the user.

Example: John Doe emails a customer from jdoe@CompanyB.com and goes out of office. The customer replies to the email and receives an out-of-office reply from jdoe@CompanyA.com instead; breaking our contractual obligation of maintaining the confidential partnerships.

Question: Does anyone know how/if this can be fixed so the out-of-office sends from the address that was originally sent to instead of only sending from the primary SMTP alias of the user?

Restrictions: I'm hoping to avoid configuring multiple mailboxes or 1-to-1 shared mailboxes for my 500+ users, and also hopefully avoiding creating a second domain or standing up more servers for this fairly trivial (from a technology standpoint) issue.

  • With SOX404 rule I use to make the technician use an email hosted on the remote business. So that the data is all for the customer site. Thus it's 100% transparent. – yagmoth555 Sep 2 '16 at 19:10
  • In this case our business partners have actually transferred the email domains in question to our direct ownership/stewardship, so I don't believe they would be willing to renegotiate such a thing at this point. Part of the agreement was to offload a lot of their own IT responsibilities. It would have been easier if IT had been involved in the planning of this contract up front to provide commentary, but as usual, IT is the last department to know about such things... – NorthVandea Sep 2 '16 at 20:24
  • New server :| or call Microsoft or such business to be able to set office365 look-like domain/hosting for each domain – yagmoth555 Sep 2 '16 at 20:48

No, and I'm not aware of any third-party software that can accomplish this either.

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.