the checklist for preparing your exchange 2007 infrastructure for exchange 2013 coexistence | 9#23

of 27 | Part 09#23 | The checklist for preparing your Exchange 2007 infrastructure

for Exchange 2013 coexistence

Written by Eyal Doron | o365info.com | Copyright © 2012-2015

THE CHECKLIST FOR PREPARING YOUR

EXCHANGE 2007 INFRASTRUCTURE FOR

EXCHANGE 2013 COEXISTENCE | 9#23

In the current article, I would like to review the subject of the required preparation

that we will need to implement in the Exchange CAS 2007 environment before or

while we are moving to the “new” Exchange 2013 coexistence environment.

In this article, we will briefly review the different “parts” that we will need to relate

to when implementing Exchange 2013/2007 coexistence environment and review in

more details the specific updates that relate to the legacy namespace that we need

to configure the different Exchange CAS 2007 services.

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Legacy namespace and the required

preparations

The implementation of the legacy namespace in Exchange 2013/2007 coexistence

requires us to make the necessary preparations such as different network

infrastructures.

The required preparations for the Exchange 2013/2007 coexistence environment,

are not considered as “rocket science” bat, on the other hand, in case that we are

not aware of the required preparation and for the specific setting of the different

“parts” the project of the Exchange 2013/2007 coexistence environment could be

safer from severe problems.





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To be able to successfully assimilate the “new legacy namespace” in the Exchange

infrastructure, we will need to implement the following steps:

1. DNS infrastructure – we will need to add the host name: legacy to the internal +

external DNS infrastructure. In the internal DNS infrastructure, the host name

legacy will be “mapped” to the internal\private IP address of the Exchange CAS

2007 server and, in the In the external DNS infrastructure; the host names

legacy, will be “mapped” to the public IP address of the Public facing Exchange

2007 CAS server.

2. Public certificate infrastructure – We will need to add the

FQDN: legacy.mail.o365info.com to the public certificate that is used by the

Exchange infrastructure.

3. Exchange CAS 2007 infrastructure – we will need to update the internal +

external URL address of the Exchange CAS 2007.

4. Firewall infrastructure – we will need to add new incoming rules that will enable

external Exchange 2007 clients to access the Public facing Exchange 2007 CAS

server.





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Exchange-2007-legacy-namespace-infrastructure-01.jpg




Just a quick quote from a Microsoft article:

“In order to support external client coexistence with CAS2007 and legacy Exchange

in your “Internet Facing AD Site”, you will (potentially) need to acquire a new

commercial certificate. As a best practice, Microsoft recommends utilizing a

certificate that supports Subject Alternative Names; however, you can utilize a

wildcard certificate as well.

This commercial certificate that will be leveraged by external clients will contain at a

minimum three SAN value (note that other scenarios may require you to add

additional values):

mail.contoso.com (your primary OWA/EAS/OA accesses URL)

autodiscover.contoso.com

legacy.contoso.com (your OWA/EAS namespace for legacy mailbox access)”








[Source of information: Transitioning from an Exchange 2007 environment to

Exchange 2007]

Exchange namespace and DNS infrastructure

In the following diagram, we can see an example to the “re point” concept. Before

the implementation of the Exchange 2013/2007 coexistence environment, the

public DNS records of the Autodiscover and the Public facing Exchange CAS server

host name were pointing to the Exchange 2007 CAS.





http://blogs.technet.com/b/jribeiro/archive/2009/11/26/transitioning-from-an-exchange-2007-environment-to-exchange-2007.aspx

http://blogs.technet.com/b/jribeiro/archive/2009/11/26/transitioning-from-an-exchange-2007-environment-to-exchange-2007.aspx




After the implementation of the Exchange 2013/2007 coexistence environment, the

public DNS records of the Autodiscover and the Public facing Exchange CAS server

host name will point to the Exchange 2013 CAS.

Additionally, we will need to add a new record to the existing DNS infrastructure:

the legacy namespace record.

In our scenario, the legacy namespace that will point to the Exchange CAS 2007 is:

legacy.mail.o365info.com

In a Split DNS infrastructure, the updates of the DNS records will need to be

implemented for the Internal DNS infrastructure and the External DNS

infrastructure,





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Reconfigure-the-records-to-point-Exchange-2013-CAS-legacy-namespace-record-01.jpg




In the following diagram, we can see an example of the required DNS configuration

settings.

Exchange 2013/2007 coexistence environment

– Internal Autodiscover infrastructure

considerations

Based on the assumption of our scenario, in which the Exchange 2007 Autodiscover

namespace infrastructure was based on the concept of Joint\contiguous

namespace, for example: autodiscover.o365info.com, we will need to verify the

implementation of the following requirements.





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Required-preparation-DNS-Infrastructure-Split-DNS-1.jpg




DNS Infrastructure – verify that the internal\external DNS infrastructure will be

updated by “mapping” the Autodiscover record to the IP address of the Exchange

2013.

Verify that the Exchange 2013 CAS will be registered at the Active Directory SCP

using the host name: autodiscover.o365info.com

In the following diagram, we can see the implementation of the internal

Autodiscover infrastructure in an Exchange 2007 environment.

1. Exchange 2007 client query Active Directory for the name of the Autodiscover

Endpoint and the answer is: autodiscover.o365info.com

2. The Exchange 2007 client query DNS for the IP address of the

host: autodiscover.o365info.com and the “DNS answer” include the IP address of

the Exchange 2007 CAS.





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Exchange-2013-2007-coexistence-Required-preparation-internal-Autodiscover-01.jpg




In the following diagram, we can see the implementation of the internal

Autodiscover infrastructure in Exchange 2013/2007 coexistence environment.

1. Exchange 2007 client query Active Directory for the name of the Autodiscover

Endpoint and the answer is: autodiscover.o365info.com

2. The Exchange 2007 client query DNS for the IP address of the

host: autodiscover.o365info.com and the “DNS answer” include the IP address of

the Exchange 2013 server.

3. The Exchange 2007 client will address the Exchange 2013 CAS, and the Exchange

CAS server will proxy the request to the Exchange 2013 mailbox server.





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Exchange-2013-2007-coexistence-Required-preparation-internal-Autodiscover-02.jpg




Public certificate and the subject of legacy

namespace

In the former section, we mentioned that we would need to create a new legacy

namespace and in the DNS infrastructure points this record to the Exchange CAS

2007.

In most the mail client protocol connectivity flow, Exchange 2007 client will try to

verify the identity of the Exchange CAS 2007 but checking his public certificate.

For this reason, we will need to Purchase a new public certificate or update an

existing public certificate to include the legacy namespace. In our

scenario: legacy.mail.o365info.com

In the following screenshot, we can see an example of a public SAN certificate that

included the legacy namespace host name: legacy.o365info.com








Other considerations

When implementing an Exchange 2013 coexistence environment, there are many

other additional elements and consideration that need to be “included” in the

preparation checklist. It’s recommend to read the detailed description that appear

in the Exchange Server Deployment Assistant





http://technet.microsoft.com/en-us/exdeploy2013/Checklist?state=2419-W-BgBEAgAAQACAAAEAAQAAAAg~&completed=True

http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Public-certificate-with-the-legacy-namespace-01.jpg




Just a little taste of the additional requirements could be:

DNS infrastructure and MX records

In a scenario of Exchange 2013 coexistence environment, we will need to point to

MX records to the “new Exchange 2013 CAS” that will be configured as the Public

facing Exchange CAS server instead of the former Exchange 2007 CAS.

Firewall infrastructure

We will need to update the Firewall rule that relates to the mail infrastructure

was pointed to the IP address of the Exchange 2007 server to the “new IP

address” of the Exchange 2013 server.

Exchange CAS 2007 legacy namespace | Basic

concepts

Before we start from the description of the “checklist” list” of the required update in

the Exchange 2007 environment, let’s briefly review the concept of the legacy name.

In our scenario, the legacy name whom we choose for “representing” the Exchange

2007 infrastructure will be: legacy.mail.o365info.com

The host name: legacy.mail.o365info.com will be mapped to the IP address of the

Exchange CAS 2007 server.

When we say that: “we need to update the Exchange CAS 2007 URL address” the

meaning is: replacing the host name part of the Exchange CAS 2007 URL address

that is allocated for the different Exchange CAS 2007 services.

The new legacy namespace that we update is related to the part of the FQDN from

the URL address of a specific Exchange web service. In other words: we don’t





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/The-new-Exchange-2007-legacy-namespace.png




change or update that “structure” of the Exchange CAS 2007 URL address but only

the server name.

For example: in case that the URL address of OWA mail services was:

https://mail.o365info.com/owa

We will update the URL address to use the “new

FQDN”: legacy.mail.o365info.com and the “new URL address” will

be: https://legacy.mail.o365info.com/owa

Implementing required updates of legacy

namespace in Exchange 2007 infrastructure

We can classify the required updates that we will need to implement in the

Exchange 2007 infrastructure into two major groups:

1. Legacy namespace updates – updates in which we will “replace” existing

Exchange CAS 2007 hosts names that was used up until now, with the “new host

name” meaning the legacy namespace.

2. “Pointing” Exchange 2007 services to the Exchange CAS 2013 infrastructure – this

part relates to additional services: Autodiscover Endpoint name and Outlook

Anywhere – external host name (RPC Endpoint name).

Before the implementation of the Exchange 2013/2007 coexistence

environment, these services was “represented” by the Exchange CAS 2007

infrastructure. When we add the Exchange CAS 2013 to the existing Exchange

2007 infrastructure, these specific services should be “pointed” to the Exchange

CAS 2013 instead of the Exchange CAS 2007.





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/The-new-OWA-URL-address-with-the-legacy-namespace.png




Updating the Exchange 2007 URL address to

use the legacy namespace

We can divide the required updates in the Exchange CAS 2007 infrastructure, into

three “sections”:

1. The Exchange CAS 2007 services that relate to providing Exchange CAS

2007 access to their mailboxes

In the section, we include three different Exchange CAS 2007 services that are used

by three different mail clients:

Exchange 2007 OWA clients – we will need to update the internal + the external

OWA URL address to use the legacy namespace.

Exchange 2007 ActiveSync clients – external Exchange 2007 ActiveSync will be

served by the Exchange CAS 2013. For this reason we need to set the external

URL address to “empty”.

Regarding the internal ActiveSync URL, we will need to set the URL address to use

the legacy namespace.

Exchange 2007 Outlook clients – in case that the Exchange CAS 2007 support

Outlook Anywhere services, we can leave the value of the “external host name”

as it is because the value is based on the primary namespace. In case that the








Exchange CAS 2007 didn’t include support for Outlook Anywhere services, we will

need to enable the Outlook Anywhere services and for the value of the “external

host name” use the host name who will be “mapped” to the Exchange CAS 2013

server.

2. Exchange CAS 2007 – Exchange web service

As mention before, in Exchange 2013/2007 coexistence environment, the element

that provides Exchange web service to the Exchange 2007 clients is the Exchange

CAS 2007.

The process in which Exchange 2007 clients are “informed” about the URL address

of their Exchange web services, is implemented as part of the Autodiscover process.

The ability of the Exchange CAS 2013 to provide Exchange 2007 client information

about the “legacy Exchange CAS 2007 infrastructure” is implemented by using the

legacy namespace.

For this reason, we will need to update the Exchange CAS 2007, Exchange, web

service value of the internal + the external URL address to use the legacy

namespace.





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3. Exchange CAS 2007 | internal Autodiscover Endpoint name

By default, each of the existing Exchange CAS servers, “register” himself at the

Active Directory SCP. In a “pre Exchange 2013 coexistence environment” the

Exchange CAS 2007 is registered in the Active Directory SCP as an “Autodiscover

Endpoint”.

In an Exchange 2013/2007 coexistence environment, we need to change the default

Autodiscover infrastructure and make sure that the only source for Autodiscover

infrastructure will be the Exchange CAS 2013.

Scenario 1: in case that the Autodiscover infrastructure is based upon a concept of

the identical host name (FQDN) for the Autodiscover Endpoint name such as:

autodiscover.o365info.com, there is no need to use an update procedure because

the update will be implemented via the DNS infrastructure. The update will be

implemented by using the IP address of the Exchange CAS 2013 instead of the

former setting, which was based on the IP address of the Exchange CAS 2007.

Scenario 2: in a scenario of “non-identical Autodiscover Endpoint names” in which

the internal Exchange server registered in the Active Directory SCP by using an

internal name,

For this reason, we will need to implement a procedure in which each of the legacy

Exchange CAS server will “re-register” himself at the Active Directory SCP but now,

using the host name of the Exchange CAS 2013.





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Providing-Exchange-web-service-Exchange-2007-clients-01.jpg




The Exchange CAS 2007 services URL address

and Host name matrix

To be able to successfully manage all the required updates that need to be

implemented in the Exchange CAS 2007 infrastructure, we can use the following

table as a “checklist.” list”.

Updating the Exchange 2007 services

The general guideline or concept is the in Exchange 2013/2007 coexistence

environment the Exchange CAS 2013 inherits the primary namespace such

as: mail.o365info.com

The legacy namespace will be ”attached” to the different Exchange CAS 2007

services and regarding other services such as: Outlook Anywhere and the internal

Active Directory address, Exchange 2007 client will use the “primary namespace”

that is “mapped” to the Exchange CAS 2013.

In our scenario, the legacy namespace that was chosen for the Exchange CAS 2007

infrastructure is: legacy.mail.o365info.com

OWA We will update the internal + external OWA URL address to use

the legacy namespace.In our scenario, the Exchange 2007 OWA

URL will be:https://legacy.mail.o365info.com/owa

ActiveSync We will update the internal ActiveSync URL address to use the

legacy namespace.In our scenario, the Exchange 2007 ActiveSync





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Providing-Autodiscover-services-Exchange-2007-clients-01.jpg




internal URL will be:https://legacy.mail.o365info.com/Microsoft-

Server-ActiveSync

Exchange

web service

We will update the internal + external Exchange web service URL

address to use the legacy namespace.In our scenario, the

Exchange 2007 OWA URL will

be:https://legacy.mail.o365info.com/EWS/Exchange.asmx

Outlook Anywhere service

With required setting that relates to Outlook Anywhere service, that we will need to

implement in the Exchange 2007 infrastructure are as follows:

1. External host name





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Verify if the Exchange CAS 2007 supports the Outlook Anywhere services.

Case 1: in case that the Exchange CAS 2007 support Outlook Anywhere services, we

will need to update the authentication protocol setting (in the next section – xxx we

will relate to the authentication protocol setting).

Case 2: in case that the Exchange CAS 2007 doesn’t support Outlook Anywhere

services, we will need to enable the Outlook Anywhere services, and for the value of

the external host name choose the host name who is “used by Exchange CAS 2013”.

For example, in our scenario, we will configure the external host name

as: mail.o365info.com

External host name

Outlook

Anywhere

We will need to verify that the value of the external host name

uses the primary namespace. In our scenario, the external host

name is: mail.o365info.com

2. External client authentication protocol

We will need to verify that the value of the “External client authentication” sets of

basic.

3. IIS authentication method

We will need to configure the value of the:” IIS authentication method“ to: basic and

NTLM








Autodiscover service internal URI.

In Exchange 2013/2007 coexistence environment, the internal (and the external)

Autodiscover services should point to the Exchange CAS 2013.

Case 1: in case that the Exchange CAS 2007 was configured to use a standard

Autodiscover namespace, such as: autodiscover.o365info.com, there is no need to

implement any updates.

Case 2: in case that the Exchange CAS 2007 was configured to use an internal name

as the Autodiscover name, we will need to update this information to point to the

Exchange CAS 2013 Autodiscover internal name.





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Using PowerShell for updating the Exchange

CAS 2007 URL address

Technically, we can use the Exchange CAS 2007 GUI interface for updating some of

the URL address such as the OWA URL address but other URL addresses such as

the URL address of Exchange web services can be updated only by using

PowerShell.

To be able to simplify the update operation, we can use a simple PowerShell script

which includes two variables: the Exchange CAS 2007 server name + the legacy

namespace.

After we update these variables, we apply the legacy namespace to all the required

Exchange CAS 2007 URL addresses.

Set the Exchange CAS 2007 services.








In our example, we will set the following Exchange CAS 2007 services:

OWA

ActiveSync

Exchange web service

The updates will include the legacy namespace that we have chosen for our legacy

Exchange 2007 infrastructure. In our scenario, the legacy namespace

is: legacy.mail.o365info.com

The Exchange CAS 2007 server name in our scenario is: CAS2007

In the following diagram, we can see that syntax of the PowerShell syntax that we

will need to use





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Set-the-Exchange-CAS-2007-services-Scenario-description.png




1. Set the Exchange 2007 OWA URL address

The PowerShell command that we use for setting the OWA URL address to use the

legacy namespace is:

PowerShell

Set-OwaVirtualDirectory "CAS2007\owa (Default Web Site)" -Ex

ternalUrl https://legacy.mail.o365info.com/owa -InternalUrl

https://legacy.mail.o365info.com/owa

The PowerShell command that we use for viewing the setting of the OWA URL

address is:

PowerShell

Get-OwaVirtualDirectory -Identity "CAS2007\owa (default Web site)" | FL identity, internalUrl, ExternalUrl

2. Set the Exchange 2007 ActiveSync URL address

The PowerShell command that we use for setting the ActiveSync URL address to

use the legacy namespace is:

PowerShell





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Update-Exchange-CAS-2007-URL-address-using-the-legacy-namespace-PowerShell-command-syntax.png




Get-ActiveSyncVirtualDirectory -Server CAS2007 | Set-ActiveSyncVirtualDirectory -InternalURL "https://legacy.mail.o365info.com/Microso

ft-Server-ActiveSync" -ExternalURL $null

The PowerShell command that we use for viewing the setting of the ActiveSync URL

address is:

PowerShell

Get-ActiveSyncVirtualDirectory -server CAS2007 | FL identity, internalUrl, ExternalUrl

3. Set the Exchange 2007 Exchange web service URL address

The PowerShell command that we use for setting, the Exchange web service URL

address to use the legacy namespace is:

PowerShell

Get-WebServicesVirtualDirectory -Server CAS2007 | Set-WebServicesVirtualDirectory -InternalURL "https://legacy.mail.o365info.com/EWS/E

xchange.asmx" -ExternalURL "https://legacy.mail.o365info.com/EWS/Ex

change.asmx"

The PowerShell command that we use for viewing the setting of the Exchange web

service URL address is:

PowerShell

Get-WebServicesVirtualDirectory -server CAS2007 | FL identity, internalUrl, ExternalUrl

Manage and update the Exchange 2007 – Outlook Anywhere settings.

In Exchange 2013/2007 coexistence environment, Exchange 2007 client Outlook

client will address the Exchange CAS 2013 and the Exchange CAS 2013 will proxy

the communication request to the Exchange CAS 2007.

To be able to “CAS to CAS” communication, we will need to set the value of

theIISAuthenticationMethods to: NTLM and basic authentication

Additionally, set the ClientAuthenticationMethod to: basic








The PowerShell command that we use for setting

the IISAuthenticationMethods authentication to use NTLM and basic is:

PowerShell

Set-OutlookAnywhere -Identity "CAS2007\Rpc (Default Web Site)" -IISAuthenticationMethods NTLM,Basic

The PowerShell command that we use for setting

the ClientAuthenticationMethod authentication to use basic is:

PowerShell

Set-OutlookAnywhere -Identity "CAS2007\Rpc (Default Web Site)" -ClientAuthenticationMethod:Basic

The PowerShell command that we use for viewing the setting of the Outlook

Anywhere settings is:

PowerShell

Get-OutlookAnywhere -Server CAS2007

Update the Exchange 2007 Autodiscover Endpoint name registration

in the Active Directory SCP





http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Update-Exchange-CAS-2007-Outlook-Anywhere-settings-PowerShell-command-syntax.png




In case that the Exchange CAS 2007 was registered at the Active Directory SCP using

an “internal name”, we will need to update the existing value of the Autodiscover

Endpoint to point the Exchange CAS 2013 Autodiscover Endpoint name.

The syntax of the PowerShell that we will us for updating and viewing the value of

theAutoDiscoverServiceInternalUri is:

In our scenario the Exchange CAS 2013 Autodiscover Endpoint

is: autodiscover.o365info.com

PowerShell

Set-ClientAccessServer -Identity "CAS2007" -AutoDiscoverServiceInternalUri "https://autodiscover.o365info.com/autodiscover/autodiscove

r.xml"

The PowerShell command that we use for viewing the setting of

theAutoDiscoverServiceInternalUri URL address is:

PowerShell

Get-ClientAccessServer -Identity CAS2007 | FL identity,AutodiscoverServiceInternalUri

Additional reading

Upgrade from Exchange 2007 to Exchange 2013

Checklist: Upgrade from Exchange 2007

Install Exchange 2013 in an Existing Exchange 2007 Organization





http://technet.microsoft.com/en-us/library/jj898581(v=exchg.150)

http://technet.microsoft.com/en-us/library/ff805032(v=exchg.150)

http://technet.microsoft.com/en-us/library/jj898582(v=exchg.150)

http://o365info.com/wp-content/gallery/exchange-2013-coexistence-09/Update-Exchange-CAS-2007-Autodiscover-Endpoint-name-PowerShell-command-syntax.png




OWA,EWS configuration in Exchange 2013/2007 coexistence

2013 – 2007 coexistence issue

Part 2: Step-by-Step Exchange 2007 to 2013 Migration

Exchange 2007/2013 CoExistence URLs

Planning and migrating a small organization from Exchange 2007 to 2013 (Part

14)

Client Connectivity in an Exchange 2013 Coexistence Environment

OWA,EWS configuration in Exchange 2013/2007 coexistence

Part 1: Step-by-Step Exchange 2007 to 2013 Migration

Upgrade from Exchange 2007 to Exchange 2013

Exchange 2013 Client Access server configuration

Exchange 2007/2013 CoExistence URLs

Script for collecting information about existing Exchange infrastructure

Generate Exchange Environment Reports using Powershell

Exchange Email Organization Report (Get-CorpEmailReport)

The Exchange 2013 coexistence article series index page





http://exchangequery.com/2014/09/24/owaews-configuration-in-exchange-20132007-coexistence/

https://social.technet.microsoft.com/forums/exchange/en-US/74bea3b9-7e31-4f13-8caa-4bd70571dc18/2013-2007-coexistence-issue

http://blogs.technet.com/b/meamcs/archive/2013/07/25/part-2-step-by-step-exchange-2007-to-2013-migration.aspx

http://silbers.net/blog/2014/01/22/exchange-20072013-coexistence-urls/

http://www.msexchange.org/articles-tutorials/exchange-server-2013/migration-deployment/planning-and-migrating-small-organization-exchange-2007-2013-part14.html

http://www.msexchange.org/articles-tutorials/exchange-server-2013/migration-deployment/planning-and-migrating-small-organization-exchange-2007-2013-part14.html

http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx

http://exchangequery.com/2014/09/24/owaews-configuration-in-exchange-20132007-coexistence/

http://blogs.technet.com/b/meamcs/archive/2013/07/25/part-1-step-by-step-exchange-2007-to-2013-migration.aspx

http://technet.microsoft.com/en-us/library/jj898581%28v=exchg.150%29.aspx

http://technet.microsoft.com/en-us/library/hh529912%28v=exchg.150%29.aspx

http://silbers.net/blog/2014/01/22/exchange-20072013-coexistence-urls/

https://gallery.technet.microsoft.com/Generate-Exchange-2388e7c9

https://gallery.technet.microsoft.com/Get-CorpEmailReport-8d708025

http://o365info.com/the-exchange-2013-coexistence-article-series-index-page

http://o365info.com/exchange-2013-coexistence-environment-and-client-protocol-connectivity-flow-the-prefix

the checklist for preparing your exchange 2007 infrastructure for exchange 2013 coexistence | 9#23

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