A client wanted to setup a rule to send an automatic reply to an email address that wasn’t being used any longer. The solution was to create an Outlook rule (server-side) that would reply to the message using a specific message and forward the message to another recipient. First create a new user and email address that you want to autoreply.

Outlook:

Create a rule to have Exchange Server send an automatic reply

1. On the Tools menu, click Rules Wizard.
2. In the Apply changes to this folder list, click the Inbox you want to create the rule for.
3. Click New.
4. Click Start from a blank rule.
5. Click Check messages when they arrive, and then click Next.
6. In the Which condition(s) do you want to check list, select the From people or distribution list check box.
7. In the Rule description list, click the underlined phrase, people or distribution list.
8. In the Type name or select from list box, type the name of each person you want to receive the custom reply, and click From after you type each name.
9. Click OK, and then click Next.
10. In the What do you want to do with the message list, select the Have server reply using a specific message check box.
11. In the Rule description list, click the underlined phrase, a specific message.
12. In the subject line and message body, type whatever information you’d like to appear in your custom reply.
13. Click Close, and when prompted to save changes, click Yes.
14. Click Next, and select the check box next to any exception that you want.
15. Click Next, and in the Please specify a name for this rule box, type a name for the rule.
16. Click Finish, and then click OK.

By default, Exchange won’t send automatic replies, here is how to do it.

Exchange 2007

1. Open Exchange Management Console
2. Expand Organization Configuration-> Hub Transport
3. In the right pane select the Remote Domains tab
4. Right click Default and choose Properties
5. On the General tab you can set which type of Out of Office Messages you will allow
   On the tab named “Format of original message sent as attachment to journal report:” you can enable or disable the automatic replying/forwarding

We also went on the old mailbox (that we are autoreplying from) and modified the deliver options (mail flow settings tab) to forward email to another mailbox. This will let send reply emails only to the old email address with the custom autoreply, but anyone who sends to the new email address won’t be bothered by the autoreply. You can also hide the mailbox so it doesn’t show up in the GAL too.

Link to other versions of Exchange too