exchange 2013 coexistence and client protocol connectivity flow | the prefix | 1#23

of 29 | Part 01#23 | Exchange 2013 coexistence environment and client protocol

connectivity flow | The prefix

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

EXCHANGE 2013 COEXISTENCE

ENVIRONMENT AND CLIENT PROTOCOL

CONNECTIVITY FLOW | THE PREFIX | 1#23

Implementing an Exchange 2013 coexistence environment, could consider a

challenging project because to be able to successfully build the “coexistence

environment”, we will need a good understanding of the Exchange 2013 CAS

architecture and the “Legacy Exchange infrastructure” (Exchange 2010 or Exchange

2007).

Additionally to the need of “comprehensive understanding” of the new and “old

Exchange infrastructure”, we need to know.

How to “combine” the Exchange 2013 infrastructure with the legacy Exchange

infrastructure.

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Understand the client protocol connectivity flow in Exchange 2013 coexistence

environment

Sound complicated and hard? I prefer to use the words: interesting and challenging!

The purpose of this following article series is to clarify the fog around the subject of

the Exchange 2013 coexistence environment.

The purpose of this article series is not to provide a “step by step” instruction for

building Exchange 2013 coexistence environment.

My main purpose was to enable the reader to understand the “logic” or the “why”

part, for doing a specific task or follow a specific instruction when implemented an

Exchange 2013 coexistence environment.

The requested result was to review the client protocol connectivity flow in the

Exchange 2013 coexistence environment of: Exchange 2013\2010 coexistence

environment and Exchange 2013/2007 coexistence environment but it’s almost





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impassable to start right ahead with the technical description of the client protocol

connectivity flow in the Exchange 2013 coexistence environment without knowing

the different parts of the Exchange architecture and infrastructure and, without

knowing the unique charters of Exchange clients such as: Outlook, OWA or

ActiveSync (mobile).

The reasons + the infrastructure for the

current Exchange 2013 coexistence

environment article series

It’s important to me to acknowledge the main reason for the current article series: a

very interesting and important lecture (channel9 TechNet) by Greg Taylor:

Microsoft Exchange Server 2013 Client Access Server Role





http://channel9.msdn.com/Events/TechEd/NorthAmerica/2013/OUC-B313#fbid=A1PB8UYvmvF

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The complementary part of this “puzzle” is an article named: Client Connectivity in

an Exchange 2013 Coexistence Environment

My wish was to clarify and simplify the information that appears in Greg Taylor

lecture and in the “client connectivity in an Exchange 2013 coexistence

Environment” article, because the common denominator of the lecture and the

article is that the “reader” is a person that is very familiar with the Exchange

architecture and infrastructure. In reality, not all of us are Veteran Exchange

Warriors to know Exchange from the moment he was created, etc.

The building blocks of Exchange 2013

coexistence environment

The current article series, is about the subject of: Exchange 2013 coexistence

environment and client protocol connectivity flow, but, there is one and a very

major problem!

To be able to understand the protocol connectivity flow in an Exchange 2013

coexistence environment, we need to be familiar with the Exchange 2007





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environment and architecture, the Exchange 2010 environment and architecture

and the Exchange 2013 environment and architecture.

The subject of “protocol connectivity flows in an Exchange 2013 coexistence

environment” deal about the relationships of Exchange 2013 infrastructure with the

legacy Exchange infrastructure (Exchange 2007, 2010), but If we want to be honest,

most of the time we do not know well each of the Exchange versions and for this

reason the task of understanding the meaning of Exchange 2013 coexistence

environment is not so simple.

My point is that before we can start with the details and the specific charters of

Exchange 2013 coexistence environment, we first need to understand the different

building block of the Exchange environment and especially, the building block and

the unique charters on the Exchange 2013 coexistence environment.

The current article serious includes 16 articles.

The “building block” that will be reviewed in this article are:

Namespace – primary namespace, legacy namespace, regional namespace.





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Public facing Exchange site and Public facing Exchange CAS server

General concept of: Exchange Legacy infrastructure

Proxy versus redirection

Exchange 2013 as a focal point concept

Public versus external Exchange infrastructure

For your information

Articles 16/23 – 19/23 are dedicated to a detailed description of Exchange 2007

client protocol connectivity flow in Exchange 2013/2007 coexistence

environment.

Articles 20/23 – 23/23 are dedicated to a detailed description of Exchange 2010

client protocol connectivity flow in Exchange 2013/2010 coexistence

environment.

You can look at the section: “The Exchange 2013 coexistence environment article

series structure” for more information about each of the article series.

The term client protocol connectivity flow

versus the term mail flow

It’s important that we distinguish between the term: “client connectivity” and

another popular term that is often used: “Mail flow”





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1. Client connectivity

If we want to simplify the whole Exchange infrastructure, we can say that the

Exchange infrastructure exists for:

Enable Exchange client access to their mailbox data.

Enable a mail client to send and receive mail.





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In the context with the Exchange environment, the term: client connectivity or client

protocol connectivity, relate to the path or the “road” between the Exchange clients

and his destination: his mailbox. In the Exchange environment, Exchange clients

cannot access directly to their mailbox or to their Exchange Mailbox server. Instead,

Exchange clients will need to address the Exchange server who holds the CAS

(Client Access Server) role, and the Exchange CAS server will have to find the “right”

way for the specific user mailbox.

The “way to the user mailbox” or the “path” to the user mailbox depends on many

variables such as the Exchange client’s mailbox version, the Active Directory site

structure, the available Exchange CAS servers, the specific mail protocol that the

Exchange clients use and so on.

The path that will be selected by the Exchange CAS server to get to the user mailbox

described as: client connectivity or client protocol connectivity.





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We can relate to the term “client protocol connectivity flow” as a “journey” that the

Exchange client must pass for

Reaching the content of his mailbox





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Getting a specific Exchange web service

The diagram display only simplified path through the client protocol connectivity





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flow because in an Exchange 2013 coexistence environment, we will see that the

“journey” is much more complicated and consists of many “steps”

2. Mail flow

The term “Mail flow”, is used for describing the path or the road that a specific mail

item will need to get through from the point that is sent by the source recipient,

until the end point in which he accepted by the “destination receipt”. The subject of:

“Mail flow” is a very essential component in the Exchange environment, but in this

article series, we will not relate to this area and instead will focus only in the subject

of client connectivity or client protocol connectivity.

The term “Exchange coexistence”

The term “Exchange coexistence” describes an environment which includes a

couple of Exchange server versions. The maximum number of “Exchange

generations” described as N-2. The meaning is that the most updated Exchange

server versions, can “living together” with former Exchange generations, up to two

generations back.





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For example: Exchange 2013 can be installed and successfully communicate with

existing Exchange 2007 and Exchange 2010 infrastructure but not with Exchange

2003 infrastructure.

Implementing the project of the Exchange

2013 coexistence environment

The amount of information that we need to know about the existing Exchange

technology, the “new Exchange technology” such as Exchange 2013 and the

combination of these technologies could be quite Overwhelming.

In simple words: if you do not know exactly what you need to do and what are the

exact task that needs to be implemented to successfully complete the migration

project, don’t do it!





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The implementation of Exchange 2013 coexistence environment is related to a

couple of different “sections” such as:

1. Mail flow – the flow of the mail that is sent by the internal Exchange recipient to

external recipients and vice versa.

2. Mailbox migration – the process of the migrating user mailboxes from the legacy

Exchange infrastructure to the Exchange 2013 Mailbox server

3. High availability – the ability to use an array of Exchange CAS server who will

enable us to implement high availability and load balancing.

4. Site resilient – the subject of building a redundant data center and in the case

that a specific datacenter is not available automatically switch Exchange client to

the “other datacenter”

5. Namespace management – the namespace that we will use for the internal

Exchange client, the namespace that we use for an external Exchange client, the

namespace that we use for legacy infrastructure, etc.

6. Client protocol connectivity flow – this is that part that relate to the way or the

path that the different Exchange mail client use for “reaching” to their mailboxes.





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Why should I use Exchange coexistence

environment?

Although we use the name “Exchange” for describing the Microsoft mail server

product, each of the Exchange versions is very different from the former Exchange

versions.

In theory, each time that is new Exchange server appear, we could pull out the new

Exchange DVD, choose yes, as the answer for: would you like to upgrade your

existing Exchange infrastructure, drink a cup of coffee and after a 15, minutes be

impressed with the new Exchange interface.

In a real life, the project of “upgrade existing Exchange infrastructure” could

consider as complex and defiantly cannot be implemented as a “one-click process”.





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The reasonable solution for a medium and large Exchange environment is to

implement the scenario which described as: Exchange coexistence environment.

The Exchange coexistence solution is a solution that was created as a “temporary

solution” for a specific time frame that will enable us to migrate the existing

Exchange infrastructure to the “new Exchange infrastructure”.

In other words: we are building two separated Exchange environments, which “live

together side by side.” The migration process is implemented by “moving” parts of

the existing Exchange infrastructure to the “new Exchange infrastructure”, until we

finish moving all the “parts” such as user mailboxes, etc. Only after a successful

migration of the data, from the “old Exchange environment” to the “new Exchange

environment”, we can “shut down” or decommission the “old Exchange

environment”.

The Exchange coexistence environment is implemented as follows:

1. We add the “new Exchange version” into the existing Exchange infrastructure.





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2. We point and direct existing Exchange services such as Autodiscover and

Exchange web services to the “new Exchange server”.

3. We start to migrate Exchange users’ mailboxes from the “old Exchange

infrastructure” to the “new Exchange infrastructure.”

4. We remove and decommission the legacy Exchange infrastructure.

The Exchange coexistence environment is required during the phase that is

requested for the completion of the migration process.

Why should I learn about Exchange

coexistence environment?

There are a couple of answers for this question:

1. Planning for the implementation of Exchange coexistence environment

In case that you need to implement a configuration of Exchange coexistence

environment, there are a lot of “details” and “parts” that you need to be aware of.

As mentioned, the purpose of current article series is not to provide you a technical

instruction of “how to” or serve as a manual of “step by step.” by step”.





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Instead, the purpose is to expand the level of your knowledge about the Exchange

coexistence environment and provide a high level view

The different component of the Exchange 2013 coexistence environment

The relationships between this component

The different connectivity flow the Exchange 2013 implemented for each of the

mail protocol and services.

The different connectivity flow the Exchange 2013 implemented for different type

of client such: internal and external Exchange mail client or different versions of

Exchange client such as: Exchange 2007, Exchange 2010 and Exchange 2013 mail

clients.

2. Troubleshooting client protocol connectivity flow Exchange coexistence

environment

It’s easy to say: “I need to troubleshoot client protocol connectivity flow in an

Exchange coexistence environment” but it’s very hard to implement a

troubleshooting process in case that you have no idea about: how does the client

protocol connectivity flow Exchange coexistence environment is implemented in

practice regarding a scenario of:

Different mail protocols.

Different Exchange services.

Different version of Exchange clients (2007, 2010, and 2013).

Different location of the mail client such as: internal versus mail clients.

The good news that the Exchange coexistence infrastructure is very interesting and

challenging. The less good news is that if you don’t spend the required time for

“understanding” this infrastructure and planning this infrastructure, you can expect

difficult times.








3. Pure curiosity

Curiosity, is not a rude word! This is the “sticky part” in which I praise glorifies the

beauty of the Exchange coexistence environment. I relay thinks that the

architecture of Exchange is really interesting and challenging, and I’m always happy

to learn and understand more and more about the Exchange architecture, and at

the same time, except that I can never understand all of this infrastructure, and

really knows each of his parts.





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Why does it have to be so complicated?

Many times when I read articles that deal with the subject of: migration to new

Exchange version, the question that appears in my mind is: Why does it have to be

so complicated?

The answer is that to be able to provide our customers a good service, in which the

transition to the “new Exchange 2013 infrastructure” will be transparent to users

and, to implement a migration that will measure in zero downtime, we will need to

work hard, learn about each of the Exchange components, make the required

preparation and so on.





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However, this “declaration” still doesn’t answer the question.

The answer to the question of:” Why does it have to be so complicated?” is because

the Exchange architecture is very rich and includes many “moving parts”,

complicated infrastructures, protocols, settings, etc. So here is\are the answers:

1. Exchange infrastructure abundance of mail protocol and services

One of the most prominent charters of Exchange architecture is what I call:

abundance of the mail protocol and services.





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Exchange infrastructure provides many web services such as: Autodiscover, the

Availability service (Free/Busy time), Automatic reply (out of office), mail tips,

calendar sharing, offline address book and much more. Regarding the subject if:

mail client, Exchange provides services for a variety of mail client such as:

Internet client that uses the mail protocols: POP3, IMAP4 and SMTP

Mobile client that uses the ActiveSync protocol.

Web client that uses HTTP and HTTPS protocol.

Outlook client that uses: RPC, RPC/HTTP, RPC/HTTPS or MAPI/HTTPS





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Add to this “salad” the subject of different authentication protocols such as: Basic,

NTLM and Kerberos and we get quite a mess.

Each of the Exchange versions relates and implements this services and protocols

in a different way and, in an Exchange coexistence environment, we will need to

make all of these protocols, and services work together.

2. Exchange multi role architecture

Exchange architecture is based upon a concept that described as: multi role

architecture. Each of the “Exchange role” has different responsibilities and specific

way for communication with the “other Exchange roles” and guesses what? Each of

the Exchange versions is implementing the “role architecture” in a different way.

For example, the multi role architecture that was very popular in the Exchange 2007

and Exchange 2010 environments are updated, and the new Exchange 2013

architecture is based on a different implementation of the multi role architecture.

Instead of “spreading” the roles between different Exchange servers, the Exchange

2013 architecture is based upon a concept in which a single Exchange server will

have most of the “Exchange roles” and the responsibility for each of the Exchange





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roles was significantly changed in the Exchange 2013 architecture. An Exchange

coexistence environment should “contain” all of this different Exchange

architectures and enable to all the different Exchange versions to work together.

3. Complex infrastructure

In the following diagram, we can see a brief summary of the modern environment

or in other words, the thing that Exchange server need to deal with. For example:

Outlook version – the term: “Outlook client” can be translated to many types of

Outlook client versions such as: Outlook 2007, 2010, and 2013. Despite the fact

that we use the term: “Outlook” for describing these clients, each of the Outlook

versions is different and implemented the communication channel with an

Exchange server in a different way.

Outlook communication protocols – at the current time, Outlook version 2013

support the following type of communication protocols: RPC, RPC/HTTP,

RPC/HTTPS or MAPI/HTTPS. So when we say a sentence such as: Outlook client is

communicating with the Exchange server, to which protocol we are referring?

Outlook – internal versus external client





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Before we start with the actual description of the client protocol connectivity flow

Exchange 2013 in a coexistence environment, it’s important to review the different

parts of the Exchange environment, the charters of these “parts” in the Exchange

legacy environment verse the Exchange 2013 environment and how to “create the

magic” that will “glue” of these parts together. In more technical words: what are

the required configurations setting that we will need to implement and what the

reason for this configuration is.





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So let’s start our journey in the mysterious and fascinating world of the Exchange

2013 coexistence environment!

The Exchange 2013 coexistence environment

article series structure

The Exchange 2013 coexistence article series as the name suggests, is a series of

articles, if we want to be more specific 23 articles.

In the following table, we can see a short description of the structure of the

Exchange 2013 coexistence article series.





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Part 00/23 The Exchange 2013 coexistence article series index page

This is the index page that will enable you to find your way around the maze of

the Exchange 2013 coexistence article series.

Part 01/23 Exchange 2013 coexistence environment and client protocol


An introduction to the subject of Exchange 2013 coexistence environment basic

terms and concepts that will be reviewed in the article series.

Part 02/23 The importance of Exchange 2013 CAS in Exchange 2013 coexistence

environment | Part 1/2

The article is the first of two, in which we will review the subject of: Exchange CAS

2013 role in an Exchange 2013 coexistence environment.





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Part 03/23 The importance of Exchange 2013 CAS in Exchange 2013 coexistence


The article is the second of two, in which we will review the subject of: Exchange

CAS 2013 role in an Exchange 2013 coexistence environment.

Part 04/23 Exchange CAS server | Proxy versus redirection

Review and explanations about the concept of: Exchange “Proxy” and “Redirect”

operation that is implemented in a client protocol connectivity flow scenario.

Part 05/23 Exchange Public infrastructure | Public versus non Public facing

Exchange site

Review and explanations about the concept of: Public versus non Public facing

Exchange site concept and architecture.

Part 06/23 Exchange web services in an Exchange 2013 coexistence


The article is the first of two, in which we will review the subject of: Exchange web

services in an Exchange 2013 coexistence environment.

Part 07/23 Exchange web services in an Exchange 2013 coexistence


The article is the second of two, in which we will review the subject of: Exchange

web services in an Exchange 2013 coexistence environment.

Part 08/23 Exchange 2013 coexistence environment and the Exchange legacy

infrastructure

In this article we will review and explain the term: “legacy” in the context of the

Exchange 2013 coexistence environment.

Part 09/23 The checklist for preparing your Exchange 2007 infrastructure for

Exchange 2013 coexistence

A preparation checklist for the project of: Exchange 2013/2007 coexistence

environment, which focus on the needed URL address updates of the Exchange

2007 CAS.

Part 10/23 The checklist for preparing your Exchange 2010 infrastructure for

Exchange 2013 coexistence

A short preparation checklist for the project of: Exchange 2013/2010 coexistence

environment, in which we review some of the components and infrastructure

that we will need to prepare

Part 11/23 Exchange 2013 coexistence environment | Autodiscover

infrastructure | Part 1/2

The article is the first of two, in which we will review the subject of: Autodiscover

infrastructure in an Exchange 2013 coexistence environment.







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Part 12/23 Exchange 2013 coexistence environment | Autodiscover

infrastructure | Part 2/2

The article is the second of two, in which we will review the subject of:

Autodiscover infrastructure in an Exchange 2013 coexistence environment.

Part 13/23 Basic concepts of Outlook connectivity in Exchange 2013 coexistence


The article is the first of two, in which we will review the subject of: outlook


Part 14/23 Exchange 2013 coexistence environment and Outlook infrastructure

| Part 2/2

The article is the second of two, in which we will review the subject of: outlook


Part 15/23 Manage legacy Exchange URL address using a PowerShell script

In this article we will review and explain how to use a PowerShell script named:

Manage Exchange CAS server settings. ps1 which can be used to simplify the

configuration setting of the legacy Exchange CAS server\s infrastructure URL

address and Outlook Anywhere settings.

Part 16/23 Client protocol connectivity flow in Exchange 2013/2007 coexistence

environment | Introduction and basic concepts| 1/4

The article is the first of four, in which we will review the subject of: client protocol

connectivity flow, in an Exchange 2013/2007 coexistence environment.

Part 17/23 Autodiscover and Outlook client protocol connectivity flow in

Exchange 2013/2007 coexistence environment | 2/4

The article is the second of four, in which we will review the subject of:

Autodiscover and Outlook client protocol connectivity flow, in an Exchange

2013/2007 coexistence environment.

Part 18/23 OWA client protocol connectivity flow in Exchange 2013/2007

coexistence environment | 3/4

The article is the third of four, in which we will review the subject of: OWA client

protocol connectivity flow, in an Exchange 2013/2007 coexistence environment.

Part 19/23 ActiveSync and Exchange web service client protocol connectivity

flow in Exchange 2013/2007 coexistence environment | 4/4

The article is the fourth of four, in which we will review the subject of: ActiveSync

and Exchange web service client protocol connectivity flow, in an Exchange


Part 20/23 Client protocol connectivity flow in Exchange 2013/2010 coexistence

environment | Introduction and basic concepts| 1/4







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The article is the first of four, in which we will review the subject of: client protocol

connectivity flow, in an Exchange 2013/2010 coexistence environment.

Part 21/23 Autodiscover and Outlook client protocol connectivity flow in

Exchange 2013/2010 coexistence environment | 2/4

The article is the second of four, in which we will review the subject of:

Autodiscover and Outlook client protocol connectivity flow, in an Exchange


Part 22/23 OWA client protocol connectivity flow in Exchange 2013/2010

coexistence environment | 3/4

The article is the third of four, in which we will review the subject of: OWA client

protocol connectivity flow, in an Exchange 2013/2010 coexistence environment.

Part 23/23 ActiveSync and Exchange web service client protocol connectivity

flow in Exchange 2013/2010 coexistence environment | 4/4

The article is the fourth of four, in which we will review the subject of: ActiveSync

and Exchange web service client protocol connectivity flow, in an Exchange












exchange 2013 coexistence and client protocol connectivity flow | the prefix | 1#23

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