Exchange server 2010: Rewrite Email address

Posted on 2012-08-21
Last Modified: 2012-08-24
Dear All,
I have 2 Edge Transport Server, with Subnet
I have 3 Exchange Server (HUC, CAS, and Mailbox Server) with Subnet
I have a legacy application server, it will automatically generation report and supporting that sends out email through exchange server.
It's designed to allow communication between individuals in two separate (program specific, non-Exchange) distribution lists.  Both of these distribution lists are populated with seemingly random email addresses (Yahoo, Gmail, Hotmail, etc).  we’re configure email relay on exchange server to allow email to outside world.
For Example,
My application is IP address will sending the email out by using external email address such as,,  through the exchange server then edge server to the outside world.
Unfortunately, send email with the header FROM of the individual in the first list, and the TO of a person in the second list.  Obviously, we're not authoritative for those domains, so we're dealing with the issue of showing up on email blacklists almost constantly since we appear to recipients as a classic spammer.
I would like to filter on Hub or Edge server all email come from my application server with IP address will rewrite all email to
Is it possible to rewrite outbound headers?
Do you have any idea or solution?
Question by:Khemarin
    LVL 52

    Expert Comment

    So do you mean your Application uses rather than ....

    Why not have it send emails to a DL internally which will forward emails to the external recipients who are members of that DL ?

    Or have Application send email to a shared mailbox and have forwarding to a DL and then route to external :)

    - Rancy

    Author Comment

    Dear Rancy,

    Thank you so much for your feedback!

    My application web server will allow all users to file their information and they mostly using their personal information email such as yahoo, hotmail, and gmail ...etc. rather than the company email address.

    The application server will send the report to them every month. For Examaple, Sender to but it is using my exchange server SMTP address ( so some emails was marked as spam by yahoo.

    I have more than 1000 users. It is very difficult to inform to all users to change their personal email to my own domain.

    So I would like to work on server side if it is possible with rewrite address?

    Do you have any idea?

    LVL 52

    Expert Comment

    Its your internal application so should be having the same email address ?
    If its like the user sending email to himself ... sorry buddy that isnt good with Public domains ... as in Private domains we can ask them to white-list the IP but i dont think Public domains will whitelist this way and the process itself has a flow :(

    Not sure about the application but maybe if it can use the Server address to send email to the subscriber rather than email showing sent by to ....... this will be blacklisted by any domain on the internet as how can my domain email address be generated by some other server and sent to me ...... Surely its a SPAM.

    - Rancy
    LVL 11

    Accepted Solution

    You can't really rewrite the "From" or "reply to" values easily. You can do that with a custom transport agent, but you need a bit of programming skills to do so. The "Clean" solution would be to simply not relay for domains you don't own as that indeed makes you a classic spammer. So if your company is like i would only relay for and noone else.

    There is an address rewriting outbound agent included as a built-in agent in ex2010, so you may wanna look into that, but i warn you - it's nothing you configure with 3 mouseclicks, it's much closer to programming than to system administration.

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