Exchange 2013 coexistence and Outlook infrastructure | Part 2/2 | 14#23 5/5 (1) 17 min read

In the current article, we will continue to review the subject of the Outlook client protocol connectivity flow in an Exchange 2013 coexistence environment. In this article, we will have a closer look at the specific charters, which build the Outlook and the Exchange relationship in this environment.

Examine thoroughly the Outlook client protocol connectivity flow

The parts which we will review are:

  1. The relationships between Exchange 2013 CAS and legacy Exchange CAS servers in Exchange 2013 coexistence environment
  2. The relationships between Exchange 2013 CAS and legacy Outlook Exchange clients in Exchange 2013 coexistence environment
  3. The required configuration setting that needed for “CAS to CAS communication” meaning:
    1. Outlook Anywhere (RPC\HTTP) support and setting on the legacy Exchange CAS servers – The requirement of enabling the option of Outlook Anywhere (RPC\HTTP) on the legacy Exchange CAS servers
    2. The authentication protocol settings-

The required setting of the authentication protocol that is involved in the Outlook client protocol connectivity flow:

  • The authentication protocol that is used by Outlook client when he needs to provide his identity to the Exchange CAS server.
  • The authentication protocol that is used by Exchange 2013 CAS when he proxy the Outlook user credentials to the Exchange CAS server legacy infrastructure.

In the last part of the article, we will provide a brief example of the implementation of the required configurations setting using PowerShell.

Article Series Table of content | Click to Expand

Exchange coexistence environment | Article Series

Exchange 2013 coexistence environment and Outlook client | The required configuration settings

To be able to demonstrate the flow in an Exchange 2013 coexistence environment, let’s use the following scenario:

Exchange site, which include Exchange CAS 2013 server + Exchange 2010 infrastructure (Exchange 2010 CAS server + Exchange 2010 Mailbox server).
An Exchange, Outlook client that his mailbox hosted at the Exchange 2010 Mailbox server, need access to his mailbox.

Note – we use an Exchange 2013/2010 coexistence environment for the demonstration, but the same logic is also implemented in Exchange 2013/2007 coexistence environment.

The Outlook client protocol connectivity flow, will be implemented as follows:

  1. Outlook client communication requests will be “pointed” to the Exchange 2013 CAS server.
  2. The communication channel between Outlook mail client and the Exchange 2013 CAS server must be implemented as “Outlook Anywhere” (RPC/HTTP/S).
    RPC over HTTP/s is the default method for Outlook client connections – there are no more direct RPC connections to the servers for Outlook clients.
  3. The Outlook client will provide the user credentials using an authentication protocol that is supported by the “server side”. The available options are: Basic, NTLM or negotiation.
  4. Because the user mailbox hosted at a “legacy Exchange infrastructure” (Exchange 2010 CAS server), Exchange 2013 CAS server, will proxy the Outlook communication request to the suitable legacy Exchange CAS server.
  5. In the process of “proxying” the request to the “legacy Exchange infrastructure” (Exchange 2010 CAS server), the Exchange CAS 2013 server will “forward” the user credentials to the “destination” legacy Exchange 2010 CAS server.
  6. To be able to “forward” the user credentials to the “legacy Exchange infrastructure” (Exchange 2010 CAS server), the authentication protocol settings for the Exchange 2013 CAS server + the “legacy Exchange infrastructure” (Exchange 2010 CAS server), must be set to NTLM.

Exchange 2010 Outlook client - Exchange 2013 coexistence environment

RPC Endpoint name versus Exchange host name

The flow of legacy Exchange, Outlook client in an Exchange 2013 coexistence environment, could be sometimes confusing.

The general concept of this flow is that legacy Exchange, Outlook clients, will need to address the Exchange 2013 CAS as their “RPC Endpoint” server and in his turn, the Exchange 2013 CAS will need to proxy their request to the appropriate legacy Exchange CAS server.

We have mentioned before that in an Exchange 2013 coexistence environment; we will need to enable the Outlook Anywhere (RPC\HTTP) on each of the legacy Exchange CAS servers.

The primary configuration parameter that when enabling Outlook Anywhere (RPC\HTTP) on the Exchange CAS server is: the “external hostname.”

The external hostname is the RPC Endpoint name who “represent” the Exchange CAS server which provides the Outlook Anywhere (RPC\HTTP) services.

When Outlook client address Exchange CAS server, looking for Autodiscover information, part of the Autodiscover information that Exchange CAS server will provide, include a “reference” to the “Exchange CAS server” that is dedicated to serving the Outlook Anywhere client or in other words, can act as the RPC Endpoint server.

In the following screenshot, we can see an example of an “Autodiscover answer” that sent to the Outlook client by the Exchange CAS server.

In our example, the Exchange CAS server “tell” Outlook client that is the RPC Endpoint server name is: europe.mail.o365info.com

The information about the RPC Endpoint server appears in the section:

Protocol: Exchange HTTP under the server parameter.

RPC Endpoint server name in the Autodiscover response

In the Exchange 2013 coexistence environment, we need to change the default Outlook client protocol connectivity flow.

Instead of the configuration in which legacy Outlook client will connect a legacy Exchange CAS server which serves as an RPC Endpoint, in the Exchange 2013 coexistence environment, we need to implement a new configuration in which native Outlook client and legacy Outlook client will address only the Exchange 2013 CAS as – RPC Endpoint server.

Additionally, we need to enable the Outlook Anywhere service on each of the legacy Exchange CAS servers.

In our scenario, we want to use the following namespace: mail.o365info.com as the name if the RPC Endpoint that will be “published” to all the Outlook clients (native Exchange 2013 client and legacy Exchange clients such as 2007/2010).

When a legacy Exchange Outlook client addresses the Exchange 2013 CAS as the: “RPC Endpoint”, the Exchange 2013 CAS will know how to proxy the legacy Exchange Outlook client request to the proper legacy Exchange CAS server.

For this reason, when we enable the Outlook Anywhere service from a legacy Exchange CAS server, such as Exchange 2007/2010 CAS, we will need to set the value of the “external host name” using the “primary namespace” such as: mail.o365info.com

The namespace (mail.o365info.com in our scenario) will point to the Exchange 2013 CAS.

Outlook client will refer to the Exchange 2013 CAS as an RPC Endpoint using the name: mail.o365info.com

When the Exchange 2013 CAS needs to Proxy the request for the legacy Exchange CAS server, he will address the legacy Exchange CAS server\s by using the server “standard host name.”

In the following diagram, we can see an example of an Exchange 2010 Outlook client protocol connectivity flow.

Exchange 2010 client address the Exchange 2013 CAS using the host name: mail.o365info.com

Exchange 2013 CAS will proxy the Outlook client request to the Exchange 2010 CAS and address the Exchange 2010 CAS using the server name: Exc2010.o365info.com

Outlook client flow A single RPC Endpoint namespace

In the following screenshot, we can see an example of the configuration setting that relates to the “external host name” in Exchange 2010 CAS.

In our example, we enable the Outlook Anywhere on the Exchange 2010 CAS + configure the value of the “external host name” to: mail.o365info.com

Exchange CAS server Outlook Anywhere - external host name

In case that you are wondering: what will happen if I use a different “external host name” for each of the existing Exchange CAS servers, the answer is that the Exchange 2013 CAS will provide a different RPC Endpoint name to Outlook client based on their “Exchange version.”

Outlook client protocol connectivity flow | The two interfaces

In the Exchange 2013 coexistence environment, Outlook client protocol connectivity flow is consisted of two parts:

  • Outlook Exchange 2013 CAS communication
  • Exchange 2013 CAS and Exchange CAS server legacy communication.

By looking at the following diagram, we can see the concept of the “two interface” or “two parts” that building the Outlook client protocol connectivity flow.

  1. The “A Part” is the area that describes the relationships between the Exchange 2013 CAS server and his Outlook client.
  2. The “B Part”, is the area that describes the relationships between the Exchange 2013 CAS server and the legacy Exchange CAS server infrastructure.

Exchange 2013 coexistence environment - Outlook client authentication protocol settings

PART A| Outlook client and the “user credentials”

The “A part” of the Outlook client protocol connectivity flow is the “circle” that exists between the Outlook client and the Exchange 2013 CAS server.

The first part of the Outlook client protocol connectivity flow, start with the “authentication” in which Outlook client will need to provide the user credentials to Exchange CAS server.

Note – if we want to be more accurate, the Outlook client protocol connectivity flow start with the Autodiscover process in which Outlook client get the name of the Exchange CAS server which serves as RPC Endpoint.

In an Exchange environment, Outlook client can provide the user credentials using one of the following authentication protocols:

  1. NTLM
  2. Basic
  3. Negotiate

Authentication process in Exchange 2013 coexistence environm

Just to make it more complicated, Exchange 2013 CAS server support to Outlook Anywhere interface: internal Outlook Anywhere interface + external Outlook Anywhere interface.

Each of these “interface”, can be configured using a different setting such as different authentication configuration.

In the Exchange 2013 environment, the “outcome” is that technically we can set two “sets” of Outlook Anywhere configuration settings:
One set of internal Outlook Anywhere client and another set for external Outlook Anywhere client while each of these “sets” uses the different authentication protocol.

To required Outlook Anywhere configuration setting implemented by using one of the following options:

  1. Exchange 2013 – Web-based management interface
  2. Exchange 2013 – PowerShell interface

The Exchange 2013 CAS server graphical (web) interface, enable us to choose the required authentication protocol. The authentication protocol that we will choose will apply to the booth of the Exchange 2013 CAS interfaces”: internal Outlook Anywhere interface + external Outlook Anywhere interface.

The disadvantage of the Exchange 2013 web-based management interface is, when we select a particular authentication protocol, the setting will apply to the booth of the Outlook Anywhere interface: the internal Outlook Anywhere interface + external Outlook Anywhere interface.

In other words, the Exchange 2013 CAS server graphical (web) interface doesn’t include an option for selecting a different authentication protocol for internal Outlook Anywhere interface versus the external Outlook Anywhere interface.

In the following screenshot, we can see that the Exchange 2013 CAS server management interface enables us to set the required authentication protocol, but the setting applied to the booth, of the “Outlook Anywhere client” (the internal + external Outlook Anywhere).

Exchange 2013 CAS server Outlook Anywhere settings

Q1: What is the recommended authentication protocol?

A1: The most simple and if I may say recommended way, is to choose the same authentication protocol for the internal + external Outlook Anywhere client.

Note that an external Outlook Anywhere client supports only the option of basic authentication.

Technically, we can set a different authentication method for internal Outlook Anywhere client versus an external Outlook Anywhere client. My mantra is: KIS – keep is the simple meaning, I like to keep it simple and use the same authentication protocol (Basic) for the both of the Outlook Anywhere client (internal + external)
Outlook Anywhere and the available authentication protocols

Just to strengthen the subjects that we have reviewed, I add some Quotes from a Microsoft article that deals with this topic:

Note the two different authentication settings that are listed. ClientAuthenticationMethod and IISAuthenticationMethods. For the detail oriented people out there, you saw that one was plural and the other singular.

When you configure OA for Basic auth, then the ClientAuthenticationMethod and IISAuthenticationMethods are both set to Basic.
The same goes for when OA is set to NTLM auth. In that case, ClientAuthenticationMethod and IISAuthenticationMethods are both set to use NTLM.

When co-existing Exchange 2007 and 2010 with Exchange 2013, we need to ensure that the correct authentication settings are in place.

There are two things that we need to pay attention to. Authentication at the IIS layer and authentication at the client layer. This is the IISAuthenticationMethods and ClientAuthenticationMethod properties respectively.

As specified in the Exchange Server Deployment Assistant, to allow CAS 2013 to redirect Outlook Anywhere connections to Exchange 2010 and 2007, Outlook Anywhere must be enabled and correctly configured on Exchange 2007 and 2010.

If Outlook Anywhere previously deployed, then ensure that their configuration will support Exchange 2013. The follow permission considerations need to address:
Client authentication, which is used to allow clients like Outlook 2013 to authenticate with Exchange correctly configured. The same consistent OA client authentication scheme should deploy on legacy CAS and CAS 2013.

Internet Information Services (IIS) authentication, which is used to allow Exchange servers to communicate must include NTLM auth.

[Source of information: Exchange 2007 And 2013 Outlook Anywhere Co-Existence ]

“In a coexistence scenario that still has 2007 or 2010 Client Access Servers, you need to enable Outlook Anywhere on each legacy Client Access Server. For instructions on enabling Outlook Anywhere for Client Access Servers running on Exchange Server 2007”

[Source of information: Outlook Anywhere ]

“Customization of Outlook Anywhere settings is optional and only needed if you want to change the settings from the default configuration. By default, Exchange pushes down the Outlook Anywhere settings by using the Autodiscover service the first time that Outlook is started”.

[Source of information: Configure Outlook Anywhere on Outlook 2013 ]

PART B | Outlook client Proxy process and the “user credentials”

The “second part” of the Outlook client protocol connectivity flow relates to the part which can be described as: CAS to CAS communication. In this part, the Exchange 2013 CAS “forward” (Proxy) the Outlook client requites to the legacy Exchange CAS server.

To be able to complete the communication channel successfully, two conditions will need to fulfil:

  1. The legacy Exchange CAS server should be configured to support Outlook Anywhere.
  2. The Exchange 2013 CAS + the legacy Exchange CAS server should be configured to support IIS Authentication Method using NTLM ( IISAuthenticationMethods: {Basic, Ntlm})

Exchange 2013 CAS and the process of Proxy the Outlook user credentials

Don’t forget the simple fact: when a “legacy Exchange server” such as Exchange 2010 CAS server, get the “proxy request” from the Exchange CAS 2013 server, he doesn’t “see” the Outlook user or directly communicate with the Outlook client.

Authentication process that is implemented in CAS to CAS communication

This is a classic scenario of “man in the middle”. The “legacy Exchange server” cannot “trust” the Outlook user, or “understand” how to route the communication request until he gets the required user credentials.

To the solution for this “trust” problem, is implemented by using an “authentication proxy mechanism” in which the Exchange 2013 CAS server “forward” (Proxy) the user credentials to the required legacy Exchange CAS server.

In theory, the process of “forwarding” the user credentials can be implemented by a variety of authentication protocols, but in reality, the only supported authentication protocol that could use for “forwarding the user credentials” is the NTLM protocol.

In simple words: to be able to implement the communication channel between the Exchange CAS 2013 server and the legacy Exchange CAS servers, we will need to verify that both of the sides support the use of the authentication protocol: NTLM

In the following diagram, we can see the Outlook client protocol connectivity flow that relates to the subject of user credentials.

  • The Outlook client authentication protocol is: Basic
  • When Exchange 2013 CAS Proxy the user credentials to Exchange 2010 CAS, the authentication protocol is: NTLM

Outlook client Proxy process and the user credentials

Exchange 2013 coexistence environment | Outlook client | Required preparations check list

Ok, I exhaust myself with the boring talks about Exchange, authentication protocol and more. So… just a quick recap:

Outlook clients and c Exchange CAS server and legacy Exchange CAS servers

Manage Exchange Outlook Anywhere settings

In the following section, we will review the way that we use PowerShell commands for creating the required configuration of the Exchange 2013 coexistence environment and the Outlook Anywhere infrastructure.

1. Viewing an existing configuration settings

The first step is to view the existing configuration setting and based upon the information, create the required configuration updates.

Example 1 : Get information about the Outlook Anywhere settings of a particular Exchange CAS server

To be able to see the Outlook Anywhere settings on the Exchange 2013 CAS server, we can use the PowerShell command:

Note – use the following command from the Exchange 2013 CAS server PowerShell console.

In the following screenshot, we can see the information about the Outlook Anywhere setting of Exchange 2013 CAS server named: STS

Mange Exchange Outlook Anywhere settings Get-OutlookAnywhere

The following values relate to the authentication protocol that the Outlook Anywhere client will use when they provide the user credentials to the Exchange 2013 CAS server.

In our scenario, the server setting configured as follows:

  • External Outlook Anywhere are instructed to use the basic authentication protocol: ExternalClientAuthenticationMethod: Basic
  • Internal Outlook Anywhere clients are instructed to use the NTLM authentication protocol: InternalClientAuthenticationMethod: NTLM
  • The Exchange 2013 CAS server IIS component supports the following authentication protocols: basic, NTLM and Negotiate: IISAuthenticationMethods: {Basic, Ntlm, Negotiate}

Example 2: Get a list of all the available Exchange 2010 CAS server, display the information about the Outlook Anywhere settings.

2. Configure Exchange CAS server Outlook Anywhere settings

The following PowerShell command syntax is an example of “all the available settings”, that relate to Exchange 2013 CAS server Outlook Anywhere settings:

3. Enable NTLM on the IIS /RPC directory of your Exchange 2007/2010 servers

Example 1: Get a list of all of the available Exchange CAS servers beside Exchange 2013 CAS servers, enable (set) the Outlook Anywhere option and configure the required IIS authentication protocol

Example 2: configure the Outlook Anywhere authentication settings of a specific Exchange CAS server (configure the required IIS authentication protocol + the Client Authentication Method).

Example 3: enable the Outlook Anywhere of a specific Exchange CAS server + configure the Outlook Anywhere authentication settings of a specific Exchange CAS server (configure the required IIS authentication protocol + the Client Authentication Method).

 

Additional reading about the subject of: Exchange 2013 and Outlook clients

Video links – general migration

General information

RPC Endpoint

Exchange 2013 coexistence | Article series index

The Exchange 2013 coexistence article series index page

0/23

Exchange 2013 coexistence environment and client protocol connectivity flow | The prefix

1/23

The importance of Exchange 2013 CAS in Exchange 2013 coexistence environment | Part 1/2

2/23

The importance of Exchange 2013 CAS in Exchange 2013 coexistence environment | Part 2/2

3/23

Exchange Public infrastructure | Public versus non Public facing Exchange site

4/23

Exchange Public infrastructure | Public versus non Public facing Exchange site

5/23

Exchange web services in an Exchange 2013 coexistence environment | Part 1/2

6/23

Exchange web services in an Exchange 2013 coexistence environment | Part 2/2

7/23

Exchange 2013 coexistence environment and the Exchange legacy infrastructure

8/23

The checklist for preparing your Exchange 2007 infrastructure for Exchange 2013 coexistence

9/23

The checklist for preparing your Exchange 2010 infrastructure for Exchange 2013 coexistence

10/23

Exchange 2013 coexistence environment | Autodiscover infrastructure | Part 1/2

11/23

Exchange 2013 coexistence environment | Autodiscover infrastructure | Part 2/2

12/23

Basic concepts of Outlook connectivity in Exchange 2013 coexistence environment | Part 1/2

13/23

Exchange 2013 coexistence environment and Outlook infrastructure | Part 2/2

14/23

Manage legacy Exchange URL address using a PowerShell script

15/23

Client protocol connectivity flow in Exchange 2013/2007 coexistence environment | Introduction and basic concepts| 1/4

16/23

Autodiscover and Outlook client protocol connectivity flow in Exchange 2013/2007 coexistence environment | 2/4

17/23

OWA client protocol connectivity flow in Exchange 2013/2007 coexistence environment | 3/4

18/23

ActiveSync and Exchange web service client protocol connectivity flow in Exchange 2013/2007 coexistence environment | 4/4

19/23

Client protocol connectivity flow in Exchange 2013/2010 coexistence environment | Introduction and basic concepts| 1/4

20/23

Autodiscover and Outlook client protocol connectivity flow in Exchange 2013/2010 coexistence environment | 2/4

21/23

OWA client protocol connectivity flow in Exchange 2013/2010 coexistence environment | 3/4

22/23

ActiveSync and Exchange web service client protocol connectivity flow in Exchange 2013/2010 coexistence environment | 4/4

23/23

Now it’s Your Turn!
It is important for us to know your opinion on this article

Summary
Exchange 2013 coexistence and Outlook infrastructure | Part 2/2 | 14#23
Article Name
Exchange 2013 coexistence and Outlook infrastructure | Part 2/2 | 14#23
Description
In the current article, we will continue to review the subject of the Outlook client protocol connectivity flow in an Exchange 2013 coexistence environment. In this article, we will have a closer look at the specific charters, which build the Outlook and the Exchange relationship in this environment.
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One Response to “Exchange 2013 coexistence and Outlook infrastructure | Part 2/2 | 14#23”

  1. Hi Eyal,

    Great article. However, there is one thing seems not correct. It is not true that “an external Outlook Anywhere client supports only the option of basic authentication”. We recommend to configure externalclientauthentication to basic is because some Reverse Proxy is not able to proxy NTLM authentication flow. If you use Microsoft TMG to publish your Exchange 2013/2016 server, then leaving the externalclientauthentication to NTLM is fine.

    For your reference:
    RPC over HTTP Authentication and Security
    https://technet.microsoft.com/en-us/library/aa996225(v=exchg.65).aspx

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