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Autodiscover flow in an Exchange onPremises environment | non-Active

Directory environment| Part 2#3 | Part
27#36

The current article and the next article, will be dedicated for detailed review of the
Autodiscover flow, that is implemented in an Autodiscover flow in an Exchange onPremises environment | non-Active Directory environment, by using the Microsoft
web-based tool, the Microsoft Remote Connectivity Analyzer (ExRCA).

Autodiscover flow in an Exchange on-Premises environment |

non-Active Directory environment | The article series
The current article is the second article in a series of three articles.
The additional articles in the series are:

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

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Autodiscover flow in an Exchange on-Premises environment | non-Active

Directory environment| Part 1#3 | Part 26#36
Autodiscover flow in an Exchange on-Premises environment | non-Active
Directory environment| Part 3#3 | Part 28#36
Note you can read more information about how to use the Microsoft Remote
Connectivity Analyzer (ExRCA) tool in the article Microsoft Remote Connectivity
Analyzer (ExRCA) | Autodiscover troubleshooting tools | Part 2#4 | Part 22#36

The essence of the Autodiscover journey

The main purpose of the Autodiscover journey that is implemented by the
Autodiscover client is to find his Autodiscover Endpoint.

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

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Technically speaking, there are many types of scenario in which the Autodiscover
client will initialize the Autodiscover process and different type of Autodiscover
clients.
For this reason, we will need to focus on specific examples of the variety of possible
scenarios.
To demonstrate the process of Autodiscover in a non-Active Directory environment,
we will review the scenario of a client that needs to create a new Outlook mail
profile, in an environment that described as non-Active Directory environment.

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

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In the following diagram, we can see the flow of the Autodiscover algorithm which
the Autodiscover client is programmed to use.

Do you get the feeling that the diagram is complicated and, by looking at the
diagram you start to feel a slight headache?
Well, I agree, but at the same time, I must inform you that this is a minimized
version of the Autodiscover workflow.
When drowning the diagram, I have dropped many parts such as the mutual
authentication process and other parts for making the diagram more digestible.
For example, regarding the security mechanism that is implemented as part of the
Autodiscover process, the Autodiscover flow description that will be provided in the
next section includes a very general reference to the security flaw that is
implemented.

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

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If you want to read more detailed information about the subject of security in
Autodiscover environment, read the article Autodiscover process and Exchange
security infrastructure | Part 20#36

Autodiscover workflow into a non-Active Directory

environment | Optional scenarios
To demonstrate some of the optional Autodiscover scenarios in a non-Active
Directory environment, lets use the following organization infrastructure:
The public domain name of the organization is o365info.com
The company has a public website that is published using the host name
o365info.com
An external user named Bob that has the E-mail address Bob@o365info.com ,
needs to create a new Outlook mail profile for connecting to his mailbox that is
hosted on Exchange On-Premise server.
Note the Autodiscover method that will be implemented cannot be based on the
Active Directory Autodiscover method because the Autodiscover client is located on
external\public network, and he doesnt have access to the organization Active
Directory.

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

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Scenario 1: company website that uses the public domain name | no

HTTPS support
The Autodiscover client (Outlook in our scenario) will take the right part of the
recipients email address and will relate to the SMTP domain name as the host
name of a Potential Autodiscover Endpoint.
Autodiscover client will contact a DNS server and query the DNS about an IP
address of a host named o365info.com
In our scenario, the DNS has an IP that is mapped to this hostname.

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

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Note that this IP address, will point to the companys public website that is not an
Autodiscover Endpoint but the Autodiscover client doesnt know it!
The Autodiscover client uses that IP address that he gets from the DNS server and
tries to check if the Potential Autodiscover Endpoint support communication using
the HTTPS protocol.
In this specific scenario, the company web site doesnt support HTTPS (doesnt have
a public certificate).

When the HTTPS communication test with the host o365info.com host fails, the
Autodiscover Client understand that he will need to move on to the additional
Autodiscover method.

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

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The Autodiscover client starts a new session, but this time; the Autodiscover client
will now try to look for a Potential Autodiscover Endpoint using the host name
autodiscover.o365info.com
In our scenario, an A record was created using the hostname- Autodiscover and the
IP address that is mapped to this hostname point to the Exchange On-Premise
server.
Autodiscover client checks if the host- autodiscover.o365info.com support HTTPS.
The Autodiscover Endpoint (Public facing Exchange CAS server) approves that he
can communicate using the HTTPS protocol.

The Autodiscover client will ask from the Autodiscover Endpoint (Public facing
Exchange CAS server) to prove his identity, by providing a public certificate.
In case that the server certificate was successfully verified, the Autodiscover client
will send his user credentials to the Autodiscover Endpoint.

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

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The last step is the step in which the Autodiscover client asks from the Autodiscover
Endpoint the required Autodiscover information for building a new Outlook
Anywhere profile.

Scenario 2: company website that uses the public domain name | HTTPS
support
The following scenario is a little confusing because, this time we deal with a public
website that is mapped to the root domain name + support HTTPS.
This scenario will cause the Autodiscover client to believe that he had found his
Autodiscover Endpoint but in the reality, the host that he tries to communicate
with, is not the required host.
Autodiscover client will contact the DNS server looking for the hostname
o365info.com

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

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After he gets the IP address, the Autodiscover client tries to check if the host (the
Potential Autodiscover Endpoint) supports HTTPS communication.
In our scenario, the company website supports HTTPS communication and has a
public certificate.

The basic assumption of the Autodiscover Endpoint is that this is the right host
and now; the Autodiscover client will generate a request for Autodiscover
information.
The request will be accepted by the host- o365info.com but this host is not an
Autodiscover Endpoint, and he doesnt understand the meaning of request for
Autodiscover information.
The Autodiscover client understands that he tries to communicate with the wrong
host and the next step is moving forward the next Autodiscover methods in
which the Autodiscover client will try to look for the Autodiscover Endpoint using a
different host name autodiscover.o365info.com

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

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Scenario 3: HTTP redirection

In this scenario, we will deviate from our original scenario that is based on
Exchange On-Premise infrastructure in favor of a scenario that is common in an
environment such as Office 365 and Exchange Online.
In this scenario, the user mailbox is hosted on the Exchange Online server.
The cloud infrastructure, doesnt really publish hostnames using the supposed
naming convention but instead, when the Autodiscover client think that he got
his Potential Autodiscover Endpoint, the host redirects him to the Office 365
Autodiscover infrastructure for continuation of the Autodiscover process.
In the following diagram, we can see that the Autodiscover client gets from the DNS
server the IP address of autodiscover.o365info.com
When he tries to check if the Potential Autodiscover Endpoint
(autodiscover.o365info.com) support HTTPS connections, he gets a negative
response.

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

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The Autodiscover client will move on to the next Autodiscover method in which he
tries to ask from the Potential Autodiscover Endpoint information about a new
name of Autodiscover Endpoint.
This method described as an HTTP redirection because the host redirects the
Autodiscover client to additional Potential Autodiscover Endpoint

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

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In the following diagram, we can see that the Autodiscover client addresses the
host-autodiscover.o365info.com using the HTTP protocol instead using the standard
HTTPS protocol.
Because the Office 365 host is aware to the process in which he needs to redirect
the Autodiscover client to other Potential Autodiscover Endpoint, the Office 365
host send the hostname- autodiscover.outlook.com in the redirection response.
Autodiscover client will try now to communicate with the new Autodiscover
Endpoint named-Autodiscover-s.outlook.com using the HTTPS protocol (I have
dropped the DNS name resolution process).
In the Office 365 environment the Autodiscover flow, will not end at this point, but
for the time being, I will end our scenario in this phase.

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

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The Autodiscover client verifies if the new Autodiscover Endpoint can

communicate using HTTPS and if the answer is yes, the Autodiscover process will
continue from this point.

Scenario 4: looking for an Autodiscover SRV record

The following scenario, describe a special Autodiscover method that is based on a
special DNS record, the SRV record.
The use of the SRV Autodiscover method enables to implement the Autodiscover
method in a non-Active Directory environment that is very similar to the
Autodiscover method in an Active Directory environment.
Until now, the Autodiscover method that the Autodiscover client use, was based on
a method in which the Autodiscover client generate or guess the Autodiscover
Endpoint name by using the right part from the recipient E-mail address (the
SMTP domain name).
In a scenario in which a specific organization owns multiple public domains, the IT
needs to configure the required DNS record for each of the domains and in

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

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addition, add the name of the Autodiscover host for each of the domains to the
server public certificate.
Using the option of the SRV record, unable to point mail client that uses a
different SMTP domain name to a single point of authority meaning, an
Autodiscover Endpoint that can serve the different client.
For example, the DNS SRV record can point a recipient from the domain
o365info.com + the domain o365info.org to the one Autodiscover Endpoint named
mail3.otherdomain.com
Its important to emphasize that the SRV Autodiscover method is the last
Autodiscover method on the list.
Only if the Autodiscover client drains out all the Autodiscover methods, which we
review in the former scenarios, only, then he will try to use the SRV Autodiscover
method.
There could be a couple of scenarios, which will lead the Autodiscover client to
use the SRV Autodiscover method.
In this scenario, the Autodiscover client tries to query the DNS server for the IP
address of the hosts o365info.com and autodiscover.o365info.com
The A record for this host was not added to the DNS deliberately.
The intention was to enforce the Autodiscover client to fail back to the SRV
Autodiscover method.
The next step of the Autodiscover client is to query the DNS for an Autodiscover
SRV record.
In our example, the SRV record was a created and was configured with the host
named mail3.otherdomain.com
The Autodiscover client will try to get the IP address of the host
mail3.otherdomain.com
When the Autodiscover finds the host, he will try to verify that the host can
communicate using HTTPS and so on.

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

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Another passable scenario is a scenario in which the Autodiscover client finds

information about a Potential Autodiscover Endpoint
named- autodiscover.o365info.com
The problem is that this host doesnt respond to an HTTPS communication
request and additionally, cannot relate to the HTTP redirection request of the
Autodiscover client.

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

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In this case, the Autodiscover client will revert to the Autodiscover method of
trying to query the DNS server about an SRV record.

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