Notes Exchange SMTP Routing Coexistence Supplimental

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 username@domain.com .................................. 9
How to populate ................................................................................................................................... 9
Set Smart Host entry pointing from Exchange 2007 to Lotus Domino ....................................................... 10
Set Smart Host entry pointing to from Lotus Domino to Exchange 2007 .................................................. 12
Test e-mail flow from Lotus Domino AUser to Exchange 2007 BUser (via Domino smart host) ................ 15
Test e-mail flow from Exchange 2007 AUser to Domino BUser (via Exchange 2007 smart host) Reply to
Domino AUser ............................................................................................................................................. 18
Test e-mail flow from Internet to Lotus Domino to Exchange 2007 (via smart host) ................................ 20
Receive Message in Exchange 2007/Outlook from Domino Smart Hosting ........................................ 22
In Outlook, reply to Internet message .................................................................................................... 23
Receive Message in GroupWise/GroupWise Client ................................................................................ 24
Set primary MX record to point to Exchange 2007 .................................................................................... 25
Summary ..................................................................................................................................................... 26

P a g e | 2 Copyright 2009 Quest Software Inc. All Rights Reserved
Copyright Quest Software, Inc. 2009. All rights reserved.

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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 e-mail routing for the duration of a co-
existence 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 (@domain.com 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 e-mail 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 e-mail Domino server and Domino Server
can e-mail Exchange Server 2007 internally so that a co-existence migration (e-mail 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 due-
diligence 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 e-mail 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:
http://www.microsoft.com/downloads/details.aspx?familyid=72A947D9-E75F-4EAE-B153-
E0B4A16442D9&displaylang=en

Note: This document does not discuss the Microsoft Transporter Suite for Lotus Domino. It shows only
how to perform SMTP e-mail routing between the Domino and Exchange 2007 Servers for e-mail co-
existence 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:
https://support.quest.com/SUPPORT/index?page=solution&id=SOL52033
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.

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 e-mail 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
Internet
Domino Server
AUser@domain.com
External
MX domain.com
FROM:Auser@domain.com
Figure 1 - E-Mail flow from Domino user to the Internet
For this example, Domino AUser sends an e-mail to an external e-mail user in a foreign e-mail system.
- Domino AUser creates an e-mail message and clicks send
- The Lotus Domino Server processes the e-mail message and determines it needs to be delivered
outside of the Domino system to the Internet
- The External User receives the Domino AUsers message.
- If the External User replies to the message, the reply to address will be Auser@domain.com

Sample Inbound Message Flow
Internet
Domino Server
AUser@domain.com
External
MX domain.com
TO:Auser@domain.com
Figure 2 - E-Mail flow from the Internet to GroupWise User
For this example, the External User sends (or replies with) an e-mail message to Auser@domain.com.
- External User creates/replies to a message to AUser@domain.com
- Message destination is determined using Internet DNS and directed to the Domino Server
- Lotus Domino Server receives e-mail message and delivers to Domino Auser

Create Exchange 2007 Environment
Internet
Domino Server
MX domain.com
AUser@domain.com
Email Policy - @domain.com
Exchange 2007 Server
External
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:
http://technet.microsoft.com/en-us/library/bb123694(EXCHG.80).aspx
- 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 e-mail, please see the following Microsoft
document titled How to Configure Authoritative Domains for the Exchange Organization
found at the following link:

The end goal is to have the Exchange 2007 Server setup such that e-mail can be sent to a mailbox-
enabled user (that receives for the @domain.com 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 e-mail for @domain.com), telnet can be used to connect to and send e-mail 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:
http://technet.microsoft.com/en-us/library/aa995718(EXCHG.65).aspx
As an example, create an Exchange 2007 Mailbox-enabled user (i.e. administrator@domain.com) and
attempt to send e-mail to it to verify that inbound e-mail messages are accepted for the @domain.com
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

Create Mailbox-enabled Users With Forwarding set to username@domain.com
Internet
Domino Server
AUser@domain.com
Email Policies - @domain.com
AUser@domain.com
External
MX domain.com
BUser@domain.com Buser@domain.com

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 mailbox-
enable 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 e-mail to Lotus
Domino. Objects are needed for future steps where e-mail 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 e-mail (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 username@domain.com (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 e-mail to Lotus Domino via the Smart Host
setting (described in section Set Smart Host entry pointing to Lotus Domino later in this document).

Set Smart Host entry pointing from Exchange 2007 to Lotus Domino
At this point, if e-mail 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 the @domain.com
domain space and will not route e-mail it accepts as authoritative. To remedy this, the Exchange 2007
Smart Host option will be utilized to send shared address space e-mail to another e-mail system.
Internet
Domino Server
Auser@domain.com
Email Policies - @domain.com
AUser@domain.com
External
MX domain.com
SmartHost=Domino Server
BUser@domain.com Buser@domain.com
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):
- E-mail message is received in Exchange 2007 (say for AUser@domain.com)
- Exchange 2007 determines that it is the authoritative messaging server for @domain.com and
finds an AD object to deliver the e-mail to (i.e. Auser@domain.com)
- When Exchange 2007 attempts to deliver the e-mail message to Auser@domain.com, it
determines that forwarding is set (via the AD targetAddress attribute) on the object which
means that Auser@domain.com does not hold e-mail (even if it is a mailbox) and the message
needs to be forwarded to the targetAddress value.
- Seeing as though the targetAddress value (AUser@domain.com) is the authoritative domain,
the Exchange 2007 server would normally fail the message and send an NDR back to the sender.

- 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 e-mail 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 AUser@domain.com and delivers the e-mail 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 '10.4.66.32' is the Domino Server IP Address

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 for
@domain.com and 2) the receiving mailbox has a targetAddress attribute value set to the same
authoritative @domain.com domain.
In this section the same will be accomplished, but in the reverse order where if in Lotus Domino 1)
receives an authoritative messages for @domain.com and 2) the receiving mailbox has a forwarding
value set (meaning not to store the email) to the same authoritative @domain.com domain it will then
send the message to Exchange 2007 via a smart host entry.
Internet
Domino Server
MX domain.com
External
Buser@domain.com
SmartHost=Exchange Server
Buser@domain.com
Auser@domain.com Auser@domain.com
Figure 8 - Set Domino Smart Host pointing to Exchange 2007 Server

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:
http://www-
12.lotus.com/ldd/doc/domino_notes/6.5.1/help65_admin.nsf/f4b82fbb75e942a6852566ac0037f284/12
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):
- E-mail message is received in Lotus Domino (say for AUser@domain.com)
- Lotus Domino determines that it is the authoritative messaging server for @domain.com and
finds an Notes User object to deliver the e-mail to (i.e. Auser@domain.com)
- When Lotus Domino attempts to deliver the e-mail message to Auser@domain.com, it
determines that Forwarding address: is set and Mail System: is set to Other Internet Mail on
the object which means that Auser@domain.com does not hold e-mail (even if it is a mailbox)
and the message needs to be forwarded to the Forwarding address: value.

The following is the Lotus Domino Server log file showing:
- Inbound message being received from the Internet (sending server cs-novell65-01.gw.cs-
targetdomain.net ) destined for AUser@domain.com
- Forwarding set on the Auser@domain.com to forward to Auser@domain.com 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

05/29/2009 02:25:42 PM SMTP Server: cs-novell65-01.gw.cs-targetdomain.net (10.4.66.33) connected
05/29/2009 02:25:42 PM SMTP Server: Message 005FBCDD (MessageID: <sa1ffe79.002@cs-novell65-01.gw.targetdomain.net>) received
05/29/2009 02:25:42 PM SMTP Server: cs-novell65-01.gw.cs-targetdomain.net (10.4.66.33) disconnected. 1 message[s] received

05/29/2009 02:25:42 PM Recipient in local Internet Domain uses Other Internet Mail system, forwarding to Smart Host

05/29/2009 02:25:43 PM Router: Transferring mail to domain CS-MIG1-EX2K7-1.DOMAIN.COM (host CS-MIG1-EX2K7-1.
DOMAIN.COM [10.4.66.241]) via SMTP
05/29/2009 02:25:43 PM Router: Transferred 1 messages to CS-MIG1-EX2K7-1. DOMAIN.COM (host CS-MIG1-EX2K7-1.
DOMAIN.COM) via SMTP
05/29/2009 02:25:47 PM Router: Message 005FBCDD transferred to CS-MIG1-EX2K7-1. DOMAIN.COM for AUser@ domain.com via
SMTP
05/29/2009 02:25:52 PM Admin Process: Searching Administration Requests database

Test e-mail 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 username@domain.com, two mailbox enabled accounts were created in Exchange
2007 with forwarding set to username@domain.com. 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 BUser@domain.com:

Figure 10 - BUser 'Forwarding address:' option set

and the Exchange BUsers forwarding will be removed as shown in Figure 11 below:
Internet
Domino Server
MX domain.com
External
Buser@domain.com
Buser@domain.com

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

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:

06/01/2009 11:39:55 AM Recipient in local Internet Domain uses Other Internet Mail system, forwarding to Smart Host

06/01/2009 11:39:56 AM Router: Transferring mail to domain CS-MIG1-EX2K7-1.DOMAIN.COM (host CS-MIG1-EX2K7-
1.DOMAIN.COM [10.4.66.241]) via SMTP
06/01/2009 11:39:56 AM Begin CD to MIME Conversion(Process: Router (00000A04:00000006), Database:
C:\Lotus\Domino\Data\mail.box, Note: 00000A2A)
06/01/2009 11:39:58 AM End CD to MIME Conversion(Process: Router (00000A04:00000006), Database:
C:\Lotus\Domino\Data\mail.box, Note: 00000A2A)
06/01/2009 11:39:58 AM Router: Transferred 1 messages to CS-MIG1-EX2K7-1.DOMAIN.COM (host CS-MIG1-EX2K7-
1.DOMAIN.COM) via SMTP

06/01/2009 10:40:00 AM Router: Message 0049EC96 transferred to CS-MIG1-EX2K7-1.DOMAIN.COM for BUser@domain.com
via SMTP

and is delivered to Exchange BUser:

Figure 13 - Notes AUser message received by Exchange BUser via Smart Host

Test e-mail 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 AUser@domain.com which will make use of the Exchange 2007 Smart Host and deliver mail to
Domino where there is an AUser mailbox that houses email.

For this example, reply to the AUser email 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 email from Exchange BUser via the Exchange 2007 smart host
*This completes the Lotus Domino to Exchange 2007 and Exchange 2007 to Lotus Domino email routing
using a single domain space via the Smart Host setting.

Test e-mail flow from Internet to Lotus Domino to Exchange 2007 (via
smart host)
At this point the MX Record for @domain.com still points to Lotus Domino. Exchange 2007 is as well
set up to receive e-mail for that domain space. It is time to test e-mail flow from the Internet to Lotus
Domino to Exchange 2007 @domain.com domain space.
Internet
Domino Server
MX domain.com
External
Buser@domain.com
Buser@domain.com

Figure 16 - Environment setup for Internet email 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).

A third messaging server (GroupWise Server) user Admin will send a message (using the GroupWise
Client) to Notes BUser using the following domain value BUser@domain.com:

Figure 17 - Sending e-mail from GroupWise Admin to Lotus BUser via the @domain.com e-mail address

Receive Message in Exchange 2007/Outlook from Domino Smart Hosting
For this demonstration, Microsoft Outlook 2007 will be used to receive e-mail for Exchange 2007 BUser.
As can be seen, the e-mail is addressed FROM:Admin@gw.targetdomain.net:

Figure 18 - Exchange BUser receiving e-mail from GroupWise Admin via Internet mail

In Outlook, reply to Internet message
For this demonstration, Microsoft Outlook 2007 will be used to reply to the e-mail sent from
admin@gw.cs-targetdomain.net. As can be seen, the TO: field is populated with admin@gw.cs-
targetdomain.net:

Figure 19 - Replying to Internet email

Receive Message in GroupWise/GroupWise Client
When this message is received in Admins GroupWise Client, the address of the sending user is
FROM:BUser@domain.com as shown below:

Figure 20 - Receiving e-mail from Exchange BUser@domain.com
Note: This is very important for e-mail reply-ability. If the reply address is not correct, e-mail 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.

Set primary MX record to point to Exchange 2007
Internet
Domino Server
MX domain.com
External
Buser@domain.com
Buser@domain.com

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 e-mail 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 e-mail coming inbound to @domain.com).
Note:
Once this is complete, the Lotus Domino server will receive *NO* inbound e-mail 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 e-mail outbound (to the Internet) as normal. Sent e-mail from both e-mail
systems will be FROM:UserName@domain.com which is desired.

Summary
The Quest Notes Migrator for Exchange User Guide makes reference to creating Sub-Domains to allow
SMTP e-mail 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:
https://support.quest.com/SUPPORT/index?page=solution&id=SOL52033

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