Lotus Domino Server and Exchange 2007 Server SMTP …support-public.cfm.quest.com/3985_notes_exchange_smtp_routing... · Lotus Domino Server and Exchange 2007 Server SMTP Routing

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 ....................................................... 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

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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.

http://www.microsoft.com/downloads/details.aspx?familyid=72A947D9-E75F-4EAE-B153-E0B4A16442D9&displaylang=en

http://www.microsoft.com/downloads/details.aspx?familyid=72A947D9-E75F-4EAE-B153-E0B4A16442D9&displaylang=en


http://www.quest.com/professional-services/


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

[email protected]

External

MX domain.com

FROM:[email protected]

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 AUser’s message.

- If the External User replies to the message, the reply to address will be ‘[email protected]’


Sample Inbound Message Flow

Internet

Domino Server

[email protected]

External

MX domain.com

TO:[email protected]

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 ‘[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 e-mail message and delivers to Domino ‘Auser’


Create Exchange 2007 Environment

Internet

Domino Server

MX domain.com

[email protected]

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. [email protected]) 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

http://technet.microsoft.com/en-us/library/aa995718(EXCHG.65).aspx


Create Mailbox-enabled Users With Forwarding set to [email protected]

Internet

Domino Server

[email protected]

Email Policies - @domain.com

[email protected]


External

MX domain.com

[email protected] [email protected]

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 ‘[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 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

[email protected]

Email Policies - @domain.com

[email protected]


External

MX domain.com

SmartHost=Domino Server


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 ‘[email protected]’)

- 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. ‘[email protected]’)

- When Exchange 2007 attempts to deliver the e-mail 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 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 (‘[email protected]’) 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 ‘[email protected]’ 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

[email protected]

SmartHost=Exchange Server

[email protected]


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 ‘[email protected]’)

- 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. ‘[email protected]’)

- When Lotus Domino attempts to deliver the e-mail 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 e-mail (even if it is a mailbox)

and the message needs to be forwarded to the ‘Forwarding address:’ value.

http://www-12.lotus.com/ldd/doc/domino_notes/6.5.1/help65_admin.nsf/f4b82fbb75e942a6852566ac0037f284/124a7258c3ec3ee785256dff004b1d1a?OpenDocument




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 [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

05/29/2009 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: <[email protected]>) 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 [email protected]”, two mailbox enabled accounts were created in Exchange

2007 with forwarding set to ‘[email protected]’. 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 [email protected]:

Figure 10 - BUser 'Forwarding address:' option set




…and the Exchange BUser’s forwarding will be removed as shown in Figure 11 below:

Internet

Domino Server

MX domain.com



External

[email protected]



[email protected]

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 [email protected] 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 [email protected] 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

[email protected]



[email protected]

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 ‘[email protected]’:

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:[email protected]’:

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

‘[email protected]’. As can be seen, the TO: field is populated with ‘[email protected]

targetdomain.net’:

Figure 19 - Replying to Internet email


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 e-mail from Exchange [email protected]

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

[email protected]



[email protected]

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:[email protected] 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:



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Lotus Domino Server and Exchange 2007 Server SMTP …support-public.cfm.quest.com/3985_notes_exchange_smtp_routing... · Lotus Domino Server and Exchange 2007 Server SMTP Routing