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Exchange Server: Auto reply from Distribution Group via Public Folder

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Exchange Server: Auto reply from Distribution Group via Public Folder

I haven’t found many useful and simple guides to set an automatic reply on mails sent to a distribution group (like in this example, for hiring purposes) and I thought creating this guide might be helpful to interested parties.

Many suggest creating Out-of-Office (OOF) rules or customizing Non-Delivery Reports (NDR’s) and there are a lot of posts discussing endless loops which these designs always initiate. Above picture shows my design which does not generate endless loops and more importantly does not cause administrative overhead and maintenance problems.

Scenario:

You wish to set and mail address (jobs@bugman.in.rs) for Human Resources Department in your company and enable automatic “Thank You for Your interest…” reply for every job application sent to that e-mail address.

Prerequisites:

001_HR_OU_BeforeYou need to have appropriate Organizational Unit (OU) created in your domain environment hosting all User Accounts nested using AGDLP strategy. In my Test  Environment I have create HR OU hosting sample users all nested in Global group G_HR (based on their business organization). I have also created Domain Local group for resource access management (not needed for this setup; just to respect the recommended role-based access control (RBAC) setup completely). G_HR is member of these DL groups.

103_Remote_Domains_Properties (Important!)Naturally, you need to have Exchange server(s) on-premises (not Hosted Exchange services and so).

Your Exchange organization (HUB Transport) must be configured to allow automatic replies:

                          1. Go to Organization Configuration → HUB Transport section and click on Remote Domain tab.
                          2. Right click Default domain name and choose Properties.
                          3. Click on Message Format tab and verify if Allow automatic replies is checked. If not, check it.


Needless to say, you have to be Domain and Exchange Administrator having all needed permissions to Active Directory and Exchange organization with login rights to all of the servers in hive.

Solution Approach:

Please use schematics diagram at the top of this post as guideline. In more detail, we will do the following:

  1. We will create new mail enabled Distribution group accepting all mail’s sent to original HR Distribution group.
    You can hide it from Exchange address lists and even choose not to send delivery reports from it, but it is not mandatory since this design is bulletproof.
  2. Then we will create special User Mailbox and Account (Reply account) also receiving all mail’s sent to this mail enabled Distribution group but using HUB ransport rule defined only for mail’s received from outside of Exchange organization.
    That way Reply account will not receive OOF’s and NDR’s sent from other Distribution group members not risking endless loop’s initiated by automatic reply’s to non-human messages.
    Also remember to use strong password for that account and set its password never to expire not risking mailbox unavailability.
    I would recommend hiding that account from Exchange address lists also.
  3. That Mailbox will have automatic forwarding rule to specially created Public Folder (Autoreply account) not retaining any mail skipping all administrative overhead since there will be no need to check that mailbox’s load and/or NDR’s.
    Only standard maintenance and backup procedures will apply to this specific Reply and Autoreply mailboxes.
  4. We will create Public Folder for autoreply purposes, accepting mail from Reply account and replying to original message sender with predefined message text.
    We will also hide this Public Folder from Exchange address lists since it is intended for external communication.
  5. Remember to define appropriate permissions to that Public Folder to HR staff.
    Always define at least one of the HR users as Public Folder Owner since you don’t want to manage someone else’s mailbox as administrator leading to heavy operation load in large organizations.
Implementation Procedure:

003_DG_HR_Properties_01004_DG_HR_Properties_02Create mail enabled Distribution group DG_HR defining jobs@bugman.in.rs as primary SMTP address to it and nesting G_HR Distribution group (containing all HR staff) in it.

I would also recommend adding your own User account as member for the duration of testing cycle.

I prefer creating mail enabled Distribution groups directly from Exchange Management Console (EMC) by clicking New Distribution Group… in Recipient Configuration → Distribution Group section.

005_DG_HR_Properties_03 006_DG_HR.Reply_Properties_01Now we will create DG_HR Reply account defining GD_HR.Reply@bugman.in.rs as primary SMTP address to it and hiding it from Exchange address lists.

Also remember to give it strong password and set it never to expire. That way you will not risk auto reply mechanism unavailability.

You can also use EMC to create that account.

008_HR_OU_AfterNow our HR OU also holds group and user we have
created as shown in the picture.




Now we need to create HUB Transport rule to include this DG_HR Reply account into mails addressed to DG_HR Distribution group (jobs@bugman.in.rs).

  1. Log in to your Exchange server hosting HUB Transport role and navigate to Organization Configuration → Hub
    Transport
    section.
  2. Choose Transport Rules tab and click New Transport Rule… action.
  3. Give it distinct name (like Job applications Reply) and clear description like “All mail sent from OUTSIDE of Exchange organization to jobs@bugman.in.rs (“DG_HR” mail enabled distribution group) forward to “DG_HR Reply” temporary user account (endless loop bulletproof setup)“.
  4. Choose the following rule conditions:
    a. From users inside or outside the organization, clicking Outside the organization as condition scope.
    b. When any of the recipients in the To field is people, adding the jobs@bugman.in.rs as recipient e-mail address.
  5. And the following rule action:
    a. Blind carbon copy (Bcc) the message to address, adding the DG_HR.Reply@bugman.in.rs as recipient e-mail address.

Use below pictures as reference:
009_HUB_Transport_Rule_01   010_HUB_Transport_Rule_02












Now we need to create Public Folder for auto reply purposes (with jobs.autoreply@bugman.in.rs as primary SMTP address).

To access Public Folder console in EMC navigate to Toolbox section and double-click Public Folder Management Console configuration management tool.

Note: If this is the first time you are creating a Public Folder remember that you have to Create a Public Folder Database first.

In the Public Folder Management Console navigate to Default Public Folders section and choose New Public Folder… action.

011_Public_Folder_01Also remember to mail enable it by right clicking it and choosing the Mail Enable option.






012_Public_Folder_02In order to successfully manage that public folder as Administrator you need to grant your user (administrator account) Send As permission by right clicking Public Folder and choosing Manage Send As Permission… from the dropdown menu.



Also remember to give that Public Folder jobs.autoreply@bugman.in.rs primary SMTP address and hide it from Exchange address lists, since it is intended for external communication only.

013_DG_HR.Reply_Properties_03Now go back to DG_HR Reply properties and set forwarding:

                            1. In EMC navigate to Recipient Configuration → Mailbox and right click DG_HR Reply mailbox choosing Properties from dropdown menu.
                            2. Select Mail Flow Settings tab, mark Delivery Options and click Properties.
                            3. Select Forward to: checkbox and jobs.autoreply@bugman.in.rs as forwarding address.

Note: Please remember to inspect if Deliver message to both forwarding address and mailbox is unchecked to minimize administrative overhead.

Administrator who will set autoreply rule by using Microsoft Outlook must have Owner and Edit All Items permissions against Public Folder.

Please check if your administrator account is Owner of the created Public Folder by using Get-PublicFolderClientPermission cmdlet in Exchange Management Shell (EMS) and looking AccessRights output:

014_EMS_Get-PublicFolderClientPermission

If you need to set required permissions to user who will configure autoreply rule, use following commands:

015_Public_Folder_Properties_01You can also check and fine-tune/set permissions on Public Folder from Public Folder Management Console by choosing Properties from right click drop down menu on desired Public Folder. Then go to Permissions tab and set desired permissions.

I would recommend giving all members of G_HR distribution group Reviewer permissions and giving specific users (like HR Manager) Owner permissions to enable that user Public Folder management rights and reduce your operative overhead.

You can also set permissions directly from Outlook (if you configured permissions correctly) by right clicking that Public Folder and choosing Properties.

Note: Remember to set Folder List view in Outlook to be able to see Public Folders.

To configure auto reply rule:

  1. Open your Microsoft Outlook
  2. Select Folder List view
  3. Right click jobs.autoreply Public Folder and choose Properties
  4. On General tab choose Folder Assistant
  5. Click Add Rule
  6. Select Reply with checkbox and click Template button
  7. Insert only desired message text (do not enter Subject and so) and click Save & Close
  8. When asked for confirmation click Yes

016_Public_Folder_Properties_02017_Folder_Assistant_01018_Folder_Assistant_02

019_Auto_Reply_Message
















Test Procedure:

This design is tested on Windows Server 2008 R2 forest functional level, using Exchange Server 2010 (with all roles installed on the same server) and Outlook 2010 using Domain Administrator account both for user and administrative purposes.

The easiest way to test this setup is to add your users account as member of mail enabled distribution group like I already have suggested and sending mail from external domain (like Gmail). You need to verify if you (with your domain account):

  1. Received mail into your company’s Outlook.
  2. Have access to Public Folder and has that Public Folder also received the same mail.
  3. Received auto reply mail into your external mail client (Gmail).

Let’s send the following job application from Gmail to jobs@bugman.in.rs:
021_Test_Send_Application
Verify have you received that mail in Public Folder (jobs.autoreply):
022_Confirm_Recive_Public_Folder

Verify have you received that same mail into you users’ mailbox (Outlook):
023_Confirm_Recive_User_Mailbox

Verify have you received autoreply in your Gmail account:
024_Confirm_Recive_Auto_Reply

Troubleshooting Section:

Distribution group members are not receiving mail from external addresses

101_Sender_AuthenticationIf your distribution group members are not receiving mail you have probably forgot to uncheck the Require that all senders are authenticated option under Message Delivery Restrictions in DG_HR’s Mail Flow Settings.

Remember, that distribution group is intended for communication with external (unknown) clients which cannot be authenticated.




I verified correctly implemented setup but it is not working or some of the setup options are not available

I don’t see Groups/Users created through EMC in ADUC console

Also, if you administer large organization and have multiple domain controllers and Exchange servers divided into several physical servers by roles; especially if you have many sites and slow link replications among them, you will need to wait for replication process to finish before testing this setup.

I would recommend two day setup, reserving second business day for test procedure.

I cannot save Template or Folder Assistant is grayed out

If you cannot set auto reply rule using Folder Assistant or save Template you messed up Public Folder permissions. Please use EMS cmdlet’s as I have suggested in this post.

External client is not receiving autoreply message and Public Folder receives mail correctly

If Public Folder receives mail but is not sending reply you forgot to Allow automatic replies as stated in Prerequisites section.

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Predrag Mirjanić

About the Author:

I am capable of working as an engineer on complicated projects or as a "one-man band" bringing the project from scratch to successful fruition. Regarding my technical skills I have quite a lot to offer. Primarily I am a Systems Administrator (Engineer). I have acquired experience in the field by installing, implementing and administering many different Microsoft based network setups in large ICT environments, in diverse industry and government companies. I am familiar with older operating systems including Linux/UNIX based systems. I have designed, installed and implemented different technologies like: Exchange, IP CCTV, BES, SCCM (specifically ZTI), network QoS optimization, and much more. I have good experience with virtualized environments (Microsoft based). I can apply my skills to help automate processes in order to reduce administrative overheads and/or human errors. I am in process of developing WAMP based (Windows, Apache, MySQL and PHP) intranet (company-wide) social networking site for document and project management purposes. Engineering hardware based cloud (powered by Linux OS) for purposes of rendering video material. Also programming several different RouterOS based MikroTik routers to deliver ultimate network management solution (QoS, bandwidth control, L7 protocol traffic control etc.).

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