My E-mail appears as spam - Troubleshooting path | Part 11#17

of 21 | 11#23 | Exchange 2013 coexistence environment | Autodiscover
infrastructure | Part 1/2
Written by Eyal Doron | o365info.com | Copyright © 2012-2015
EXCHANGE 2013 COEXISTENCE
ENVIRONMENT | AUTODISCOVER
INFRASTRUCTURE | PART 1/2 | 11#23
In the following article, we will review the subject of Autodiscover infrastructure in
an Exchange 2013 CAS environment. In a modern Exchange environment, we can
say that the Autodiscover services consider the infrastructure for all the rest of the
different Exchange infrastructure.
The Exchange Autodiscover Architecture can consider as complex and
sophisticated, especially in an Exchange 2013 coexistence environment.
My point: we need to understand the fundamentals of Autodiscover infrastructure
in Exchange 2013 CAS to be able to understand the rest of the process and the
client protocol connectivity flow that will be reviewed in the next articles in the
current article series.

My basic assumption is that: you (my reader) are familiar with the concept of
Exchange Autodiscover and what does the Autodiscover “do”. But a quick review of
the Autodiscover infrastructure will not kill anyone.
The article is the first of two, in which we will review the subject of: Autodiscover
infrastructure in an Exchange 2013 coexistence environment. The next article
is: Exchange 2013 coexistence environment | Autodiscover infrastructure | Part 2/2
Exchange Autodiscover service | The element,
the components and charters
Exchange clients, are completely depended upon the Exchange Autodiscover
services.
Let’s start with a few observations about the Exchange Autodiscover infrastructure:

1. The element that provides the Autodiscover information to Exchange
clients.
The element that needs to “feed” the Exchange clients with the Autodiscover
information is: “Exchange CAS server”
2. Autodiscover dynamic datainformation
The Autodiscover datainformation is not a “static information”. Instead, the
Autodiscover considered as a dynamic information that is generated each time for
each of the Exchange clients.
3. The element that generates the Autodiscover information.
In former versions of Exchange: Exchange 2007 and Exchange 2010, the “element”
that was responsible for generating the Autodiscover information was the
Exchange the hold the Exchange CAS server role.

In the Exchange 2013 environment, the element that generates the Autodiscover
information is the Exchange 2013 that holds the Exchange Mailbox role. Exchange
2013 CAS server is responsible for “delivering the Autodiscover information and
Exchange Mailbox server is responsible for “creating” the Autodiscover information.
4. Autodiscover content | Exchange coexistence environment
As mentioned, the Autodiscover information considers as a “dynamic data” because
the Autodiscover data are customized for each of the different types of Exchange
client version. For example, the Autodiscover information that is provided to the
Exchange 2007 clients (an Exchange client that his mailbox is hosted on Exchange
2007 Mailbox server) is different than the Autodiscover information that will be

provided to the Exchange 2013 clients (an Exchange client that his mailbox is
hosted on Exchange 2013 Mailbox server).
5. Autodiscover content | External versus internal Exchange client
The Autodiscover information that Exchange CAS servers provide to his client,
depend on the “physical location” of the Exchange client. In case that the Exchange
CAS server recognizes that the Exchange client considered as “internal client”, the
Autodiscover information that will be provided to the Exchange client, will include
information about internal resources.
The meaning of “internal resources” is: FQDN and URL address that include
“internal names” of Exchange servers. Internal Exchange names are not “exposed”
to the public network or in other words, an external Exchange mail client cannot
“reach” these Exchange servers.
In case that the Exchange CAS server recognizes that the Exchange client considers
as “external client”, the Autodiscover information that will be provided to the client
will include information about external resources.
The meaning of “external resources” is: information about Public facing Exchange
CAS servers. The information will include public FQDN + URL address.
6. Autodiscover content | different mail client (mail protocols)
The Autodiscover information, which Exchange CAS server provide to his client,
depends on the “type” of the Exchange client.
The meaning of the term: ”different mail client” is related to mail clients such as:
OWA mail client, Mobile (ActiveSync) mail client and Outlook mail client. Each of this
mail clients uses different communication protocol and uses the Exchange
Autodiscover in a different way.
For example: Outlook client use protocol such as: RPC, RPC over HTTP, and MAPI
over HTTP verse’s mobile Exchange client that uses the ActiveSync protocol.
The Autodiscover information that Exchange provides two “different type of
Exchange clients” is not identical. For example: the Autodiscover information that is
provided to mobile Exchange client (ActiveSync client) is different than the
Autodiscover information that is provided to the Outlook client.

Exchange Autodiscover and Exchange 2013
coexistence environment
From the information that we are reviewing in the former section, it’s clear that the
“job” of providing Autodiscover information is not simply because, there are many
elements and factors that are involved in the Autodiscover infrastructure.
In an Exchange 2013 coexistence environment, we add an additional element to
this complex environment because in an Exchange coexistence environment, there
a couple of Exchange CAS servers that are able to provide Autodiscover
informationservices.
So now, we need to understand how Exchange 2013 “fits” into the Autodiscover
infrastructure and what are the required changes or updates that need to be
implemented in an Exchange 2013 coexistence environment.

To be able to clarify that the subject of Autodiscover infrastructure and Exchange
2013 coexistence environment, let’s divide the Exchange infrastructure into two
parts:
1. Public Exchange infrastructure and Autodiscover services
2. Internal Exchange infrastructure and Autodiscover services
The concept of: Exchange 2013 CAS as an
Autodiscover focal point
To be able to understand better the Autodiscover infrastructure in an Exchange
environment, it’s important to understand the concept which I described as:
“Exchange Autodiscover focal point”. The meaning of this concept is that the
Exchange 2013 CAS needs to be configured as the “main Autodiscover point” or the
“primary Autodiscover point” relates to the realm of:
1. The type of Exchange clients – the Exchange 2013 CAS will need to be configured
as an Autodiscover Endpoint and serve, all the types of Exchange client that
exists in Exchange 2013 CAS such as: Exchange 2013 client, Exchange 2010 client
and Exchange 2007 clients.
2. External and internal Exchange client – Exchange 2013 CAS will need to be
configured as an Autodiscover Endpoint and serve External and internal
Exchange clients.

The content of the Autodiscover file
Throughout this article and the rest of the article in this article series, we will
mention many time terms such as: Autodiscover information, Autodiscover
response, etc.
The important thing that we will need to understand is that the Autodiscover
information that is provided by the Exchange CAS server to “his” Autodiscover client
is not a “static file” but instead the opposite.

The Autodiscover “answer” that the Exchange CAS server provides is generated
each time in a unique way for each of the separated Autodiscover client requests.
We can say that the Exchange CAS server is tailoring the Autodiscover Suit based on
the very specific measurements of his Autodiscover client.
The Autodiscover “answer” that the Exchange CAS 2013 provides to the
Autodiscover client depends on two major factors:
1. The Exchange client version
The meaning of the term “Exchange client version”, is the Exchange mailbox server
version for host the mailbox of a specific Exchange client user. For example, when
we use the term: Exchange 2007 client, the meaning is Exchange client that his
mailbox is hosted on the Exchange 2007 mailbox server.
The information that appears in the “Autodiscover answer” that is sent to the
Autodiscover client, will be customized to the specific version of the Exchange
client.
In the following diagram, we can see that the Exchange CAS 2013 is generating a
custom Autodiscover answer for each of the different Autodiscover clients. For
example, the content with the Autodiscover information that is provided to the

Exchange 2007 client is different than the content of the Autodiscover information
that is provided to the Exchange 2013 clients.
2. The Exchange client “physical location”
The term “Exchange client physical location” relate to the location from which the
Exchange CAS server address or connect the Exchange CAS server.
The main classification for Exchange client “location” is: internal Exchange
infrastructure versus public Exchange infrastructure. The “roles” that apply to these
two separated Exchange environments are different, the charter of the
communication channel between the Exchange client, and his Exchange CAS server
is different and the Autodiscover information that will be provided to the internal
Exchange client is different from the Autodiscover information that will be provided
to external Exchange client.
An additional classification that we can use that relates to “internal Exchange
clients” is the Exchange site or the Active Directory site in which they are physically
located.

For example: in a scenario of multiple Exchange sites, the Autodiscover information
that the Exchange CAS server provides includes a specific “Exchange site
information”. For example, in case that the Autodiscover client is an Exchange client
from Madrid site, the Autodiscover information that will be provided to the
Exchange client, will include information (URL address, host name, etc.) of Exchange
resources that are located at the Madrid site.
3. The Exchange server version
The Autodiscover content, depend on the version of the Exchange server who
provides the Autodiscover information.
For example: Exchange CAS 2013 is more “advanced” than the former version of
Exchange CAS servers and the Autodiscover information that he provides to his
clients, include additional parameters and connection methods.
For example, Exchange CAS 2013 provides additional “section” in the Autodiscover
information that described as: EXHTTP

For these reasons, it’s important that all the Exchange clients (the different versions
of Exchange clients) will address only the Exchange CAS 2013 for Autodiscover
information and additionally, that the Outlook client software version, will be
updated to enable the Outlook client to “understand” the new language” that the
Exchange CAS 2013 use.
You can read additional information about this subject in the article: When, if and
how do you modify Outlook Providers?
4. The Exchange client type
Additional factors that affects the content if the Autodiscover information that
Exchange CAS server provide is the “type” of the Exchange client. Technically, all the
Exchange client types: Outlook, ActiveSync and OWA, use the Autodiscover
infrastructure, but the “main Autodiscover client” is Outlook and second is the
ActiveSync Exchange client.
When Exchange CAS server recognizes that the Exchange client is Outlook or a
“Mobile client” (ActiveSync), the Autodiscover information that the Exchange CAS
server generates is different because each of these clients, needs a different
parameters, etc.

External and internal Exchange client |
Exchange 2013 CAS as Autodiscover Endpoint
1. Public Exchange infrastructure the concept of: “central Autodiscover
point” in Public Exchange environment, is not a new concept.
The realization of this concept is as follows: even if the Exchange public
infrastructure, consists of multiple Public facing Exchange sites, the Autodiscover
service will always be “pointed” into a single focal point.
In other words, although in theory, each of the Public facing Exchange sites, can
provide Autodiscover services, the Autodiscover will be based on a central concept

in which one specific Public facing Exchange CAS server or to be more accurate, one
specific Public facing Exchange CAS server, will be responsible for providing the
Autodiscover services for all the Exchange clients from the different Exchange sites.
Note – there is an exception to the concept of “Exchange Autodiscover focal point”
in a public environment in a scenario of GeoDns that is based upon a multiple
“Autodiscover points”. The Exchange clients (the Autodiscover client) will be pointed
to their Public facing Exchange CAS server based on their geographical location.

2. Internal Exchange infrastructure in an Exchange 2013 coexistence
environment.
The concept of “Exchange Autodiscover focal point” is implemented also, on the
internal Exchange environment in a scenario of the Exchange 2013 coexistence
environment. In an Exchange coexistence environment, we are using two or three
different Exchange server versions. Although since Exchange 2007 version, each of
the Exchange server “know” how to use the Autodiscover infrastructure, there a
major difference between each of the Exchange server versions (Exchange 2007,
2010 and 2013).
This “deference” relates to many “parts” and also to the Autodiscover architecture
and implementation. To be able to “unified” the different Exchange versions,
another concept which I derived as: “backward compatibility” is implemented. The
“backward compatibility” concept is implemented by using the ”newer Exchange
server version” as an Autodiscover focal point.
For example, in an Exchange site that uses an Exchange 2013 coexistence
environment which includes Exchange 2007 servers and Exchange 2010 servers,
the Autodiscover infrastructure will be “pointed” to the Exchange 2013 CAS server.

Public Exchange infrastructure and
Autodiscover services
To be able to demonstrate the concept of Exchange Autodiscover in a Public
environment, let’s use the following scenario: An organization that has three Public
facing Exchange sites.
 Site 1 and site 3 are “Public facing Exchange sites” and site 2 is an internal
Exchange site (non-public site).
 The organization Public domain name is: o365info.com
 The public Autodiscover record is: autodiscover.o365info.com
General concept of Autodiscover client protocol connectivity flow
When an external Exchange user looks for an Autodiscover Endpoint (Public facing
Exchange CAS server), the Autodiscover record (autodiscover.o365info.com), will
point the Exchange clients to the Public facing Exchange CAS server in site 1.
 Scenario 1: User mailbox hosted on Exchange Mailbox servers is site 1.
The Autodiscover information that Exchange CAS server in site 1 will provide,
includes the information about the “site 1 public Exchange infrastructure” (URL
address with the public FQDN of the Public facing Exchange CAS server in site
1).Each of the Exchange client requests, will be accepted by the Public facing
Exchange CAS server in site 1 and will be proxied by the public facing Exchange
CAS server to “internal Exchange infrastructure” such as the Exchange Mailbox
server in site 1.
 Scenario 2: User mailbox hosted on Exchange Mailbox servers is site 2
because, site 2, is not a Public facing Exchange site (Intranet site), the
Autodiscover information that Exchange CAS server in site 1 will provide, includes
the information about the “site 1 public Exchange infrastructure” (URL address
with the public FQDN of the Public facing Exchange CAS server in site 1).
Each of the Exchange client requests will be accepted by the Public facing
Exchange CAS server in site 1 and, will be proxied by Public facing Exchange CAS
server to the internalprivate Exchange infrastructure in site 2.
 Scenario 3: User mailbox hosted on Exchange Mailbox servers is site 3.
Because site 3, is a Public facing Exchange site, the Autodiscover information that
Exchange CAS server in site 1 will provide, includes the information about the
“site 3 public Exchange infrastructure” (URL address with the public FQDN of the

Public facing Exchange CAS server in site 3).The “site 3 Exchange client” gets the
Autodiscover information, which includes the URL address with the public FQDN
of the Public facing Exchange CAS server in site 3. From now on, the “site 3
Exchange client” will address directly the Public facing Exchange CAS server in
site 3.
Note – there are exceptions to this description such as ActiveSync clients.

Exchange CAS 2013 – the Successor of legacy
Exchange CAS servers
In an Exchange 2013 coexistence environment, the Exchange 2013 CAS server
serves as an Autodiscover Endpoint for all the different Exchange clients.
Exchange CAS 2013 server will “replaces’” or “Inherits” the role of the legacy
versions of Exchange CAS server, such as: Exchange 2007 CAS, or Exchange 2010
CAS.
The reason for this “replacement” is because the Exchange CAS 2013 server is can
handle Autodiscover request from all the different Exchange clients: native
Exchange 2013 Autodiscover client and at the same time, Exchange CAS 2013
server, will “know what do” with an Autodiscover request of legacy Exchange clients
such as: Exchange 2007 and Exchange 2010 clients.
The opposite is not true, meaning: Exchange 2007, 2010 CAS server will not handle
correctly an Autodiscover request of “advanced Exchange clients” such as Exchange
2013 clients.

To be able to demonstrate the concept of Public facing Exchange 2013 CAS in
Exchange 2013 coexistence environment, let’s use the following scenario: A
company, which has one Public facing Exchange sites.
Note – in the current scenario, we will demonstrate the Autodiscover connectivity
flow by using a scenario of a company that has only one Public facing Exchange
sites. I avoid from using the charters of the former scenario (a scenario in which the
company has multiple Public facing Exchange sites) to simplify the logic and the
understanding if the Autodiscover connectivity flow in a public environment + an
Exchange environment that described as Exchange 2013 coexistence environment.
 The company Exchange site is based on Exchange 2013 coexistence
environment, which includes the following Exchange server versions: Exchange
2007, Exchange 2010 and Exchange 2013.
 The organization Public domain name is: o365info.com
 The public Autodiscover record is: autodiscover.o365info.com
 The legacy Exchange 2007 namespace is: legacy.mail.o365info.com
When an external Exchange user looks for an Autodiscover Endpoint (Public facing
Exchange CAS server), the Autodiscover record (autodiscover.o365info.com), will
point the Exchange clients to the Exchange 2013 Public facing Exchange CAS server.
In most of the “best-practice implementation” of Exchange 2013 coexistence
environment, the Autodiscover information that is provided to Exchange 2010
clients, and Exchange 2013 clients are identical.
The Autodiscover information process and infrastructure that is implemented with
an Exchange 2007 client are different because the Autodiscover information will
include “pointers” to the Exchange 2007 infrastructure that will be “represented” by
the legacy namespace.

Scenario 1: Exchange 2013/2010 client (User mailbox hosted on Exchange
2013 or Exchange 2010 Mailbox server).
When the Public facing Exchange 2013 CAS server recognizes that the Autodiscover
client is Exchange 2013/2010 client, the Autodiscover information that the Exchange
2013 CAS provides, includes the “public URL address” of the different Exchange
services that in our scenario, point to the same Public facing Exchange 20123 CAS
server.
For example: the Exchange web services URL address that will appear in the
Autodiscover information will be: https://mail.o365info.com/EWS/Exchange.asmx

Scenario 2: Exchange 2007 client (User mailbox hosted on Exchange 2007
Mailbox server).
When the Public facing Exchange 2013 CAS server recognizes that the Autodiscover
client is an Exchange 2007 client, the Autodiscover information that the Exchange
2013 CAS provides, includes URL address that will point the Exchange 2007 clients
to the Public facing Exchange 2007 CAS server.
The Exchange 2007 client, “gets the Autodiscover information” that includes the URL
address with the legacy public FQDN of the Public facing Exchange 2007 CAS server
and when the Exchange 2007 client (such as Outlook client), needs to use a specific
Exchange web service, the Exchange 2007 client will use the public legacy
namespace of the Exchange 2007 CAS.
For example: the Exchange web services URL address that will appear in the
Autodiscover information will be: https://mail.o365info.com/EWS/Exchange.asmx
The Exchange 2013 coexistence article series index page

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