How To Send E Mail From An Exchange 2007 To A Domain Name Address Book On A Domain Address Book (For A Domain) On A Pc Or Mac Xp (For An Ipod) On An Ipo (For Windows 2007) On Your Ip

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1 Lotus Domino Server and Exchange 2007 Server SMTP Routing using Smart Hosts Supplemental - Version 1.1, Dated June 2, 2009 Contents Purpose... 4 Current Lotus Domino Environment... 5 Sample Outbound Message Flow... 5 Sample Inbound Message Flow... 6 Create Exchange 2007 Environment... 7 Create Mailbox-enabled Users With Forwarding set to [email protected]... 9 How to populate... 9 Set Smart Host entry pointing from Exchange 2007 to Lotus Domino Set Smart Host entry pointing to from Lotus Domino to Exchange Test flow from Lotus Domino AUser to Exchange 2007 BUser (via Domino smart host) Test flow from Exchange 2007 AUser to Domino BUser (via Exchange 2007 smart host) Reply to Domino AUser Test flow from Internet to Lotus Domino to Exchange 2007 (via smart host) Receive Message in Exchange 2007/Outlook from Domino Smart Hosting In Outlook, reply to Internet message Receive Message in GroupWise/GroupWise Client Set primary MX record to point to Exchange Summary... 26

2 Copyright Quest Software, Inc All rights reserved. This guide contains proprietary information, which is protected by copyright. The software described in this guide is furnished under a software license or nondisclosure agreement. This software may be used or copied only in accordance with the terms of the applicable agreement. No part of this guide may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying and recording for any purpose other than the purchaser's personal use without the written permission of Quest Software, Inc. Warranty The information contained in this document is subject to change without notice. Quest Software makes no warranty of any kind with respect to this information. QUEST SOFTWARE SPECIFICALLY DISCLAIMS THE IMPLIED WARRANTY OF THE MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE. Quest Software shall not be liable for any direct, indirect, incidental, consequential, or other damage alleged in connection with the furnishing or use of this information. Trademarks Quest is a trademark of Quest Software, Inc. Other trademarks and registered trademarks used in this guide are property of their respective owners. Quest Software, Inc. World Headquarters 5 Polaris Way Aliso Viejo, CA USA [email protected] U.S. and Canada: Please refer to our Web site for regional and international office information. Quest Software complies with U.S. Export Control laws. Consequently, Quest Software will not ship products to or provide support to anyone in prohibited destinations as defined by the U.S. Department of Commerce. For a copy of the current export administration regulations, please visit their website at: P a g e 2

3 Quest Support Quest Support is available to customers who have a trial version of a Quest product or who have purchased a commercial version and have a valid maintenance contract. Quest Support provides around the clock coverage with SupportLink, our web self-service. Visit SupportLink at From SupportLink, you can do the following: Quickly find thousands of solutions (Knowledgebase articles/documents) Download patches and upgrades. Seek help from a Support engineer. Log and update your case, and check its status. View the Global Support Guide for a detailed explanation of support programs, online services, contact information, and policy and procedures. P a g e 3

4 Purpose The Quest Notes Migrator for Exchange User Guide makes reference to creating Sub-Domains (Step 5: Create a Temporary Subdomain for the Migration) to allow SMTP routing for the duration of a coexistence migration. This can be done but does add complexity to the setup. Another method is when the same domain space is being used from Domino to Exchange as an example), the Domino/Exchange 2007 smart host settings can be used to assist in mail routing. This document will attempt to give high-level detail on what a current Domino SMTP routing would look like. It will then go on to show what it takes to introduce the Microsoft Exchange 2007 environment. Once the Microsoft Exchange 2007 environment is introduced, this documentation will go over creating Smart Host entries so that Exchange 2007 can Domino server and Domino Server can Exchange Server 2007 internally so that a co-existence migration ( route-ability) can take place. It will also go over a typical flow of steps such that each activity can be implemented in order. This document also includes testing activities to be sure the actions are performed correctly to ensure routing is indeed working. Note: This document encompasses a very simple one Domino Server, one Exchange 2007 server scenario. Where environments are more complex, the end-user may need to perform additional duediligence to ensure that SMTP routing between the Domino and Exchange 2007 and Internet environments is sound. Note: Free/Busy is not possible with only SMTP routing between Domino Server and Exchange 2007 server. If Free/Busy is a business requirement (as it is not a Quest product requirement), then please review the Microsoft documentation for the Microsoft Transporter Suite for Lotus Domino found at the following link titled Microsoft Transporter Suite for Lotus Domino : E0B4A16442D9&displaylang=en Note: This document does not discuss the Microsoft Transporter Suite for Lotus Domino. It shows only how to perform SMTP routing between the Domino and Exchange 2007 Servers for coexistence only (with no Free/Busy). Note: Please also see Quest solution SOL52033 titled Video Guide: Notes Migrator for Exchange at the following link for details on activities, checklists and scenarios: This document is provided as is with no warranties. This document does not cover every possible scenario nor take (end-user) specific environmental variables into consideration. It is provided to give example of a simple structure. If the end-user environment falls out of the scope of what this document can provide and the end user requires further assistance with the environmental setup, engaging Professional Services via your Quest Account Manager is highly recommended (and may be necessary) to ensure a successful and timely migration. P a g e 4

5 Current Lotus Domino Environment For the purpose of this demonstration, a simple one Lotus Domino Server will be used. The following example environment will be used to show current flow from the internal Lotus Domino Server users to external (Internet) users (and vice-versa). This is a typical environment that should already be existing. Sample Outbound Message Flow External MX domain.com Internet FROM:[email protected] [email protected] Domino Server Figure 1 - flow from Domino user to the Internet For this example, Domino AUser sends an to an external user in a foreign system. - Domino AUser creates an message and clicks send - The Lotus Domino Server processes the message and determines it needs to be delivered outside of the Domino system to the Internet - The External User receives the Domino AUser s message. - If the External User replies to the message, the reply to address will be [email protected] P a g e 5

6 Sample Inbound Message Flow External MX domain.com Internet Domino Server Figure 2 - flow from the Internet to GroupWise User For this example, the External User sends (or replies with) an message to [email protected]. - External User creates/replies to a message to [email protected] - Message destination is determined using Internet DNS and directed to the Domino Server - Lotus Domino Server receives message and delivers to Domino Auser P a g e 6

7 Create Exchange 2007 Environment External MX domain.com Internet Domino Server Exchange 2007 Server Policy Figure 3 - Create new Exchange 2007 Environment For this action, create a new Exchange 2007 installation. Notes: - Installing and configuring Microsoft Exchange 2007 is beyond the scope of this document. For more information on installing Microsoft Exchange 2007, please see the following Microsoft documentation titled How to Perform a Typical Installation Using Exchange Server 2007 Setup found at the following link: - For more information on post installation tasks for Microsoft Exchange 2007, please see the following Microsoft article titled Post-Installation Tasks found at the following link: - Once installation and configuration is complete on the Microsoft Exchange 2007 Server, be sure to set the accepted domain for the primary domain space of domain.com. For more information on setting the accepting domain for , please see the following Microsoft document titled How to Configure Authoritative Domains for the Exchange Organization found at the following link: P a g e 7

8 The end goal is to have the Exchange 2007 Server setup such that can be sent to a mailboxenabled user (that receives for address space). There are a few more items to setup to make this scenario work correctly, but to test if Exchange 2007 is set up correctly at this point (to receive ), telnet can be used to connect to and send to Exchange 2007 as noted in the following Microsoft TechNet Article titled How to Use Telnet to Test SMTP Communication found at the following link: As an example, create an Exchange 2007 Mailbox-enabled user (i.e. [email protected]) and attempt to send to it to verify that inbound messages are accepted for domain space. - Example of the accepted domain.com from the Exchange Management Console Organization Configuration Hub Transport Accepted Domains dialog: Figure 4 - Accepted 'domain.com' Domain P a g e 8

9 Create Mailbox-enabled Users With Forwarding set to External MX domain.com Internet Domino Server Exchange 2007 Server Policies Figure 5 - Create Mailbox-Enabled Users with forwarding For this step, there needs to be a method to pre-populate users in Active Directory (and to mailboxenable and set forwarding too). These pre-populated objects will serve a few purposes: - Populating the Exchange 2007 Global Address List (GAL) so that when the first user is cut-over (migrated) to Exchange 2007, they can open the GAL and see all the same users they did when housed in Lotus Domino - Forwarding objects in Exchange 2007 for when Smart Hosts is used to forward to Lotus Domino. Objects are needed for future steps where is received in Exchange 2007 but is forwarded to Lotus Domino using the Exchange 2007 Smart Host (later described in section Set Smart Host entry pointing to Domino). For the Exchange 2007 Smart Host to work there needs to be an Exchange 2007 object (contact, mail-enabled or mailbox-enabled) that has the Active Directory targetaddress (forwarding) value set. Without this object, Exchange 2007 will not accept the (at all) and will deliver an NDR to the original sender. How to populate One method is to use the Microsoft Transporter Suite (see Microsoft Transporter Suite User Guide for more details), another method is to manually create the Active Directory (AD) objects. Once users are populated, the users need to be Exchange Mailbox-enabled. Methods to do this can be via Quest Notes Migrator for Exchange (see User Guide for more details) or manually. Once Active Directory objects are mailbox-enabled, forwarding needs to be set to [email protected] (which can also be accomplished using Quest Notes Migrator for Exchange (see User Guide for more details) or manually). These forwarding objects will be used at a later time to send to Lotus Domino via the Smart Host setting (described in section Set Smart Host entry pointing to Lotus Domino later in this document). P a g e 9

10 Set Smart Host entry pointing from Exchange 2007 to Lotus Domino At this point, if is sent to Exchange 2007 Mailbox-enabled objects (with forwarding set), the e- mail will not be delivered. This is due to that Exchange 2007 is Authoritative for domain space and will not route it accepts as authoritative. To remedy this, the Exchange 2007 Smart Host option will be utilized to send shared address space to another system. External MX domain.com Internet SmartHost=Domino Server Domino Server Exchange 2007 Server Policies Figure 6 - Set Exchange 2007 Smart Host pointing to Domino Server To set up Exchange Server 2007 to deliver messages to an alternate messaging system, please see the following Microsoft article titled How to Configure Exchange 2007 to Route Messages for a Shared Address Space found at the following link: The way of thinking of how the smart host within Exchange 2007 works is (for this example): - message is received in Exchange 2007 (say for [email protected] ) - Exchange 2007 determines that it is the authoritative messaging server and finds an AD object to deliver the to (i.e. [email protected] ) - When Exchange 2007 attempts to deliver the message to [email protected], it determines that forwarding is set (via the AD targetaddress attribute) on the object which means that [email protected] does not hold (even if it is a mailbox) and the message needs to be forwarded to the targetaddress value. - Seeing as though the targetaddress value ( [email protected] ) is the authoritative domain, the Exchange 2007 server would normally fail the message and send an NDR back to the sender. P a g e 10

11 - But due to the fact that a Smart Host value is set, Exchange 2007 determines that it cannot process the message internally and delivers the message to the Smart Host system (which in this case is the Lotus Domino Server). - The Lotus Domino Server receives the message and determines that it is the authoritative messaging server for [email protected] and delivers the message to the Domino AUser. - Example of the new Smart Host Send Connector from the Exchange Management Console Organization Configuration Hub Transport Send Connectors dialog: Figure 7 - Smart Host Settings where ' ' is the Domino Server IP Address P a g e 11

12 Set Smart Host entry pointing to from Lotus Domino to Exchange 2007 In the previous section Set Smart Host entry pointing from Exchange to Lotus Domino, Exchange was configured to send mail to the Domino Server in the event that 1) it receives authoritative messages and 2) the receiving mailbox has a targetaddress attribute value set to the same domain. In this section the same will be accomplished, but in the reverse order where if in Lotus Domino 1) receives an authoritative messages and 2) the receiving mailbox has a forwarding value set (meaning not to store the ) to the same domain it will then send the message to Exchange 2007 via a smart host entry. External Internet MX domain.com SmartHost=Domino Server Domino Server [email protected] [email protected] Exchange 2007 Server [email protected] [email protected] SmartHost=Exchange Server Figure 8 - Set Domino Smart Host pointing to Exchange 2007 Server P a g e 12

13 To set up Domino to deliver messages to an alternate messaging system, please see the following Domino article titled Setting up a smart host found at the following link: 12.lotus.com/ldd/doc/domino_notes/6.5.1/help65_admin.nsf/f4b82fbb75e942a ac0037f284/12 4a7258c3ec3ee785256dff004b1d1a?OpenDocument Figure 9 Local Internet domain smart host: set to the Exchange 2007 server FQDN name (cs-mig1-ex2k7-1.domain.com) The way of thinking of how the smart host within Domino works is (for this example): - message is received in Lotus Domino (say for [email protected] ) - Lotus Domino determines that it is the authoritative messaging server and finds an Notes User object to deliver the to (i.e. [email protected] ) - When Lotus Domino attempts to deliver the message to [email protected], it determines that Forwarding address: is set and Mail System: is set to Other Internet Mail on the object which means that [email protected] does not hold (even if it is a mailbox) and the message needs to be forwarded to the Forwarding address: value. P a g e 13

14 The following is the Lotus Domino Server log file showing: - Inbound message being received from the Internet (sending server cs-novell65-01.gw.cstargetdomain.net ) destined for [email protected] - Forwarding set on the [email protected] to forward to [email protected] with Mail System: set to Other Internet Mail for Auser - Smart host value will be used (in this case the fully qualified domain name (FQDN) of the Exchange 2007 server CS-MIG1-EX2K7-1. DOMAIN.COM ) - Message delivered to Exchange 2007 server 05/29/ :25:42 PM SMTP Server: cs-novell65-01.gw.cs-targetdomain.net ( ) connected 05/29/ :25:42 PM SMTP Server: Message 005FBCDD (MessageID: <[email protected]>) received 05/29/ :25:42 PM SMTP Server: cs-novell65-01.gw.cs-targetdomain.net ( ) disconnected. 1 message[s] received 05/29/ :25:42 PM Recipient in local Internet Domain uses Other Internet Mail system, forwarding to Smart Host 05/29/ :25:43 PM Router: Transferring mail to domain CS-MIG1-EX2K7-1.DOMAIN.COM (host CS-MIG1-EX2K7-1. DOMAIN.COM [ ]) via SMTP 05/29/ :25:43 PM Router: Transferred 1 messages to CS-MIG1-EX2K7-1. DOMAIN.COM (host CS-MIG1-EX2K7-1. DOMAIN.COM) via SMTP 05/29/ :25:47 PM Router: Message 005FBCDD transferred to CS-MIG1-EX2K7-1. DOMAIN.COM for AUser@ domain.com via SMTP 05/29/ :25:52 PM Admin Process: Searching Administration Requests database P a g e 14

15 Test flow from Lotus Domino AUser to Exchange 2007 BUser (via Domino smart host) At this point, both the Domino Smart Host and Exchange 2007 smart host settings are configured and point to the opposite messaging systems. In the section titled Create Mailbox-enabled Users With Forwarding set to two mailbox enabled accounts were created in Exchange 2007 with forwarding set to Any mail sent to these accounts would traverse over the Smart Host value to the Domino server. At this point we want to validate that the smart host settings will work both ways (from Domino to Exchange 2007 and from Exchange 2007 to Domino). To do this we need to change (or flip) the forwarding options of one of the example accounts. For this example, the Domino BUser will be set to forward to Figure 10 - BUser 'Forwarding address:' option set P a g e 15

16 and the Exchange BUser s forwarding will be removed as shown in Figure 11 below: External Internet MX domain.com SmartHost=Domino Server Domino Server [email protected] [email protected] Exchange 2007 Server [email protected] [email protected] SmartHost=Exchange Server Figure 11 - Set Domino Auser to forward, remove Exchange AUser's forwarding - For the first step to test if the smart host value is set and working correctly, log into Domino AUser and create a new mail message addressed to Domino BUser and send the message: Figure 12 - Notes AUser sending mail to Notes BUser P a g e 16

17 As seen in the Domino logs, Lotus Domino spots that the object has forwarding set and will deliver the message to Exchange 2007 via the Smart Host setting: 06/01/ :39:55 AM Recipient in local Internet Domain uses Other Internet Mail system, forwarding to Smart Host 06/01/ :39:56 AM Router: Transferring mail to domain CS-MIG1-EX2K7-1.DOMAIN.COM (host CS-MIG1-EX2K7-1.DOMAIN.COM [ ]) via SMTP 06/01/ :39:56 AM Begin CD to MIME Conversion(Process: Router (00000A04: ), Database: C:\Lotus\Domino\Data\mail.box, Note: 00000A2A) 06/01/ :39:58 AM End CD to MIME Conversion(Process: Router (00000A04: ), Database: C:\Lotus\Domino\Data\mail.box, Note: 00000A2A) 06/01/ :39:58 AM Router: Transferred 1 messages to CS-MIG1-EX2K7-1.DOMAIN.COM (host CS-MIG1-EX2K7-1.DOMAIN.COM) via SMTP 06/01/ :40:00 AM Router: Message 0049EC96 transferred to CS-MIG1-EX2K7-1.DOMAIN.COM for [email protected] via SMTP and is delivered to Exchange BUser: Figure 13 - Notes AUser message received by Exchange BUser via Smart Host P a g e 17

18 Test flow from Exchange 2007 AUser to Domino BUser (via Exchange 2007 smart host) Reply to Domino AUser To test reply-ability, we can take the Outlook message received in Exchange 2007 BUser and reply to it. As shown in Figure 11, if Exchange BUser sends mail to Exchange AUser, Exchange AUser has forwarding set to which will make use of the Exchange 2007 Smart Host and deliver mail to Domino where there is an AUser mailbox that houses . P a g e 18

19 For this example, reply to the AUser as shown in Figure 13: Figure 14 - Reply to Notes AUser from Exchange BUser and check Domino AUser to see if it has been received which it has: Figure 15 - AUser receiving from Exchange BUser via the Exchange 2007 smart host *This completes the Lotus Domino to Exchange 2007 and Exchange 2007 to Lotus Domino routing using a single domain space via the Smart Host setting. P a g e 19

20 Test flow from Internet to Lotus Domino to Exchange 2007 (via smart host) At this point the MX Record still points to Lotus Domino. Exchange 2007 is as well set up to receive for that domain space. It is time to test flow from the Internet to Lotus Domino to Exchange domain space. External MX domain.com Internet SmartHost=Domino Server Domino Server Exchange 2007 Server SmartHost=Exchange Server Figure 16 - Environment setup for Internet sent to Lotus BUser For this demonstration, forwarding will be set on Lotus BUser and removed from Exchange 2007 mailbox BUser (the same scenario as Figure 11 above). P a g e 20

21 A third messaging server (GroupWise Server) user Admin will send a message (using the GroupWise Client) to Notes BUser using the following domain value [email protected] : Figure 17 - Sending from GroupWise Admin to Lotus BUser via address P a g e 21

22 Receive Message in Exchange 2007/Outlook from Domino Smart Hosting For this demonstration, Microsoft Outlook 2007 will be used to receive for Exchange 2007 BUser. As can be seen, the is addressed : Figure 18 - Exchange BUser receiving from GroupWise Admin via Internet mail P a g e 22

23 In Outlook, reply to Internet message For this demonstration, Microsoft Outlook 2007 will be used to reply to the sent from As can be seen, the TO: field is populated with : Figure 19 - Replying to Internet P a g e 23

24 Receive Message in GroupWise/GroupWise Client When this message is received in Admin s GroupWise Client, the address of the sending user is FROM:[email protected] as shown below: Figure 20 - Receiving from Exchange [email protected] Note: This is very important for reply-ability. If the reply address is not correct, will not be delivered correctly to the desired user. If this test does not succeed, please review the environment and do not continue until this test can be performed successfully. P a g e 24

25 Set primary MX record to point to Exchange 2007 External Internet MX domain.com SmartHost=Domino Server Domino Server Exchange 2007 Server SmartHost=Exchange Server Figure 21 - Point MX Records to Exchange 2007 This step is the cutover! At this point, the environment is set up such that Exchange 2007 can forward messages to the Lotus Domino Server and the Lotus Domino Server can receive them (via the Exchange 2007 Smart Host). Also Lotus Domino Server can Exchange 2007 via the Lotus Domino Smart Host setting. With this said, the next item is to flip or point the external DNS MX record from the current Lotus Domino Server to the Exchange 2007 Server (for Internet coming inbound ). Note: Once this is complete, the Lotus Domino server will receive *NO* inbound other than the e- mails delivered from Exchange 2007 via the Smart Host setting. Both Exchange 2007 and Lotus Domino server will continue to route outbound (to the Internet) as normal. Sent from both systems will be FROM:[email protected] which is desired. P a g e 25

26 Summary The Quest Notes Migrator for Exchange User Guide makes reference to creating Sub-Domains to allow SMTP routing for the duration of a co-existence migration. It lacks in details on how to achieve the setup and how the routing flow will look like but also the fact that the use of Smart Hosts is simpler and easy to configure. Besides mentioning using certain Quest Products to automate certain actions, all activities done within this document can be accomplished without using any Quest Products (using native tools instead). This is stressed as installing Quest Notes Migrator for Exchange does not make the environment work. Special steps and considerations need to be taken in the said environment to be sure that when it comes time to use Quest Notes Migrator for Exchange to automate and then migrate mailboxes, the environment will be ready and the migration will flow as desired (and in a timely fashion). Given this, scoping the environment, taking inventory, then setting up and testing the actions made are very important pre-migration activities that need to be accomplished prior to any attempt at migrations and co-existence. This hope is that this document can be used as a reference and a guide to show how one simple environment is set up such that it can be utilized as example for customer environments and assisting in pre-migration setup to ensure that a co-existence migration will work as desired. Note: Please also see Quest solution SOL52033 titled Video Guide: Notes Migrator for Exchange at the following link for details on activities, checklists and scenarios: P a g e 26