Outlook Test E-mail AutoConfiguration | Autodiscover troubleshooting tools | Part 1#4 | Part 21#36

Page 1 of 20 | Outlook Test E-mail AutoConfiguration | Autodiscover troubleshooting tools

| Part 1#4 | Part 21#36

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

Outlook Test E-mail AutoConfiguration

| Autodiscover troubleshooting tools |

Part 1#4 | Part 21#36

In the current article, we will review one of the most useful and “strongest”

Autodiscover troubleshooting tools, Outlook client built-in tool named: Test E-mail

AutoConfiguration.

Autodiscover Troubleshooting tools | The article series

The article series include the following articles:

http://o365info.com/outlook-test-e-mail-autoconfiguration-autodiscover-troubleshooting-tools-part-1-of-4-part-21-of-36


https://il.linkedin.com/in/eyaldoron1

http://o365info.com/


| Part 1#4 | Part 21#36


1. Outlook Test E-mail AutoConfiguration | Autodiscover troubleshooting tools

| Part 1#4 | Part 21#36

2. Microsoft Remote Connectivity Analyzer (ExRCA) | Autodiscover

troubleshooting tools | Part 2#4 | Part 22#36

3. Microsoft Connectivity Analyzer (MCA) | Autodiscover troubleshooting tools |

Part 3#4 | Part 23#36

4. Using Fiddler for Autodiscover troubleshooting scenarios | Part 4#4 | Part

24#36

Q: What is the purpose of the Outlook Test E-mail AutoConfiguration tool?

A: The Outlook Test E-mail AutoConfiguration tool, enable us to view the “behind

the scene” of the Autodiscover process.

By using the option of- “Test E-mail AutoConfiguration”, we can get a clear view of

1. The methods that the Autodiscover client (Outlook) use such as LDAP query,

DNS query by using Root domain name and so on

2. The content of the Exchange server Autodiscover response that includes

different type of information such as – information about the available

Exchange web services URL addresses and more.

Outlook Test E-mail AutoConfiguration tool | charters

advantages and disadvantages

Advantages

The Outlook Test E-mail AutoConfiguration tool, have two main prominent

advantages:

1. Outlook built-in tool

The Test E-mail AutoConfiguration is part of the Outlook client meaning, there is no

need to download dedicated tools or access an external website (such as in the

ExRCA scenario).

All we need to do is just – on the click on the Outlook icon on the bottom taskbar

while we press the CTRL key on the keyboard. I have no idea for the mandatory







http://o365info.com/microsoft-remote-connectivity-analyzer-exrca-autodiscover-troubleshooting-tools-part-2-of-4-part-22-of-36


http://o365info.com/microsoft-connectivity-analyzer-mca-autodiscover-troubleshooting-tools-part-3-of-4-part-23-of-36

http://o365info.com/microsoft-connectivity-analyzer-mca-autodiscover-troubleshooting-tools-part-3-of-4-part-23-of-36

http://o365info.com/using-fiddler-for-autodiscover-troubleshooting-scenarios-part-4-of-4-part-24-of-36

http://o365info.com/using-fiddler-for-autodiscover-troubleshooting-scenarios-part-4-of-4-part-24-of-36


| Part 1#4 | Part 21#36


requirement of pressing the CTRL key because, if we wouldn’t press the CTRL key,

the option of Test E-mail AutoConfiguration will not appear.

2. Inspect Autodiscover session in Active Directory environment and a non-Active

Directory environment

This is the charter, which distinguishes the Outlook Test E-mail

AutoConfiguration from the rest of the Autodiscover troubleshooting tools.

As far as I know, the only tool that enables us to inspect the Autodiscover process in

an Active Directory environment is – the Outlook Test E-mail AutoConfiguration.

All the rest of the Microsoft Autodiscover troubleshooting tools that we will review

in the next articles such as – the ExRCA (Exchange Remote Connectivity

Analyzer) and MCA (Microsoft Connectivity Analyzer) are built for analyzing the

Autodiscover process that is implemented in a non-Active Directory environment.

Disadvantages

1. Non-complete description of the Autodiscover process

The results are, the output that we get from Outlook Test E-mail

AutoConfiguration tool doesn’t include the complete information about all the

steps that were involved in the Autodiscover flow.







http://o365info.com/microsoft-connectivity-analyzer-mca-autodiscover-troubleshooting-tools-part-3-of4-part-26-of-36


| Part 1#4 | Part 21#36


For example, we cannot see “Autodiscover flow” in which the Autodiscover client

addresses the local Active Directory by using an LDAP query or the flow in which the

Autodiscover client address the DNS server – we cannot see to which DNS server

the Outlook client access, what was the IP address that was returned by the DNS

server to the Outlook client etc.

2. The chicken and the egg syndrome

One of the most popular scenarios in which we would need to use the Outlook

Test E-mail AutoConfiguration toll is the scenario, which can be described as –

“cannot create a new Outlook mail profile”.

In this case, we would like to analyze the Autodiscover workflow so, we would be

able to find the cause of the problem that prevents us from completing the task of-

“cannot create a new Outlook mail profile”.

The funny thing is that in this scenario, the option of – Outlook Test E-mail

AutoConfigurationtool is not available for use because, we don’t have an Outlook

mail profile.

In the section Tip – Outlook Test E-mail AutoConfiguration , creating a demo

Outlook profile we will review a little trick that will help us to overcome this

limitation.





http://o365info.com/outlook-test-e-mail-autoconfiguration-autodiscover-troubleshooting-tools-part-1-of-4-part-21-of-36/#SUB-2

http://o365info.com/outlook-test-e-mail-autoconfiguration-autodiscover-troubleshooting-tools-part-1-of-4-part-21-of-36/#SUB-2


| Part 1#4 | Part 21#36


Scenario + infrastructure configuration

To demonstrate the use of Outlook Test E-mail AutoConfiguration option, we will

base our test of the following scenario:

We want to be able to get a look at the Autodiscover flow that is implemented

between the Autodiscover client (Outlook client in our scenario) and Autodiscover

Endpoint (Exchange CAS server).

The organization mail infrastructure details are:

On-Premise Active Directory domain name –o365info.local

Organization public domain name – o365info.com

Exchange On-Premise servers – the organization Exchange environment includes

three Exchange CAS servers. The FQDN of these servers is

– o365info.local, ex02.o365info.local and sts.o365info.local






| Part 1#4 | Part 21#36


In our scenario, we will like to check the Autodiscover process of a user named John

that uses the E-mail address- [email protected]

The desktop that we use for performing the Outlook Test E-mail

AutoConfiguration is a domain member is located at the company internal

network.

Using the option of Outlook Test E-mail

AutoConfiguration

To be able to use the option of Test E-mail AutoConfiguration, use the following

instructions:

On the right bottom of the task bar, click on the small arrow






| Part 1#4 | Part 21#36


Choose the CTRL Key

Click on the Outlook icon

Choose the option of Test E-mail AutoConfiguration….

Type the email address of the recipient, which we want to check his ability to

access the Autodiscover services

Type the recipient password (number 1 in the screenshot)

Un-check the option of – Use Guessmart

Un-check the option of – secure Guessmart Authentication (number 2 in the

screenshot)

Click on the Test option

Note – the option of the Guessmart is an old method that is not used anymore.

For my opinion, this option should have been removed a long time ago, but at the






| Part 1#4 | Part 21#36


current time, it’s important to uncheck this option to avoid a “mess” of the test

results.

Analyzing the test results of the Outlook Test E-mail

AutoConfiguration

The result of the Outlook Test E-mail AutoConfiguration is displayed using three

different tabs.

Just a quick reminder, in our scenario, the Desktop from which we execute the

Outlook

Test E-mail AutoConfiguration is a domain joined desktop.

The meaning is that – Outlook client will start with an Autodiscover method that

should be implemented in an “Active Directory based environment”

Log tab

The Log tab “tell us” what was the Autodiscover method that was used by the

Autodiscover client (Outlook) for finding the required Autodiscover Endpoint

(Exchange CAS On-Premise server).

In our scenario, Outlook finds the required Exchange server\s list by sending an

LDAP query to local Active Directory.

The method is described as SCP (number 2).

The Autodiscover address the Autodiscover Endpoint by using the following URL –

https://autodiscover.o365info.com/Autodiscover/Autodiscover.xml

In the Log result (number 2), we can see that the “mission complete successfully”

meaning that

Outlook managed to locate a local Exchange CAS server

Outlook managed to address the Exchange server

Outlook managed to complete all of the required steps such as authentication






| Part 1#4 | Part 21#36


The Exchange server sends to the Autodiscover client the required information

(the Autodiscover.xml file).

Results Tab

The result tab includes information about the “Exchange services” that are available

for the Exchange client.

1. Exchange availability services (number 1)

The Exchange Availability services (Free\Busy time) are provided by Exchange server

named –mail.o365info.com and, the URL address for accessing this service is –

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

2. Automatic reply or OOF (Out Of Office)

The Exchange service is provided by Exchange server named

– ex02.o365info.local and, the URL for accessing this service is –

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





Page 10 of 20 | Outlook Test E-mail AutoConfiguration | Autodiscover troubleshooting

tools | Part 1#4 | Part 21#36


Note – at first glance is look like a mistake, because the OOF URL is identical to the

Exchange Availability services. The reason for the “identical URL” is that Exchange

uses the EWS (Exchange Web Services) URL as a “focal point” for providing a couple

of services such as: Availability serviced (Free\Busy time) services, OOO, Mail tips

and so on.

3. Unified message

Anther capability of Exchange server is to provide the services of – Unified

messaging.

We can see the URL that the client will need to use in case that he needs to use

unified messaging.








On the next “section” we can see the Exchange server setting that was sent to the

Outlook client that required for the configuring the Outlook Anywhere settings.

The feature of “Outlook Anywhere”, enable the Outlook client to get access to

“internal Exchange services” when the client is located on a public network.

The “client” (Outlook) needs to have details such as:

Protocol name – in our scenario the protocol is HTTP (number 4)

Exchange server name (number 5) – usually this is the “public name” of the

Exchange server who configured as “RPC proxy server” that provides the “server

side” of the Outlook Anywhere services. In our scenario, the server name is

– mail.o365info.com

Encryption requirement (number 6) – The Outlook Anywhere service mandatory

requirement is to encrypt the communicating channel.

The encryption is implemented by using the SSL protocol

Authentication (number 7) – this is the section that describes the “Type of

Authentication”. Outlook Anywhere service is based on a mutual authentication

process, in which the Autodiscover client needs to identify the Autodiscover

Endpoint (the server will provide a public certificate) and after the identification

process successfully completed, the Autodiscover client will need to provide his

credentials to the “server”.

Certificate principal name- msstd (number 8) – the client (Outlook) that is configured

to use the Outlook Anywhere service, will look for the “server name” in the

certificate that the server sends to the Autodiscover client.








XML Tab

The XML tab includes the content of the Autodiscover response that was sent to the

Autodiscover client (Outlook).

Using the XML tab, we can see the information that was sent from the Autodiscover

Endpoint to the Autodiscover client using the Autodiscover communication

channel.

The Autodiscover response includes many details.

In our example, we will review only a sample of the information that appears in the

XML Autodiscover response.








Note- XML format is based on a concept of opening and closing tag (<tag>) that

defines the type of information and, the “information” is included between the

opening and closing tags.

1. Action tag (number 1)

In the <Action> tag, we can see that the value is – settings.

The meaning is that – the information that appears in this section, should be used

for “creating a new Outlook mail profile).

2. Type (number 2)

The <Type> tag “instruct” Outlook client about the configuration setting of a specific

Outlook provider. In the specific section, the information is relevant for the EXCH

Outlook provider.

Additional reading

The Autodiscover Service and Outlook Providers – how does this stuff work?





http://blogs.technet.com/b/exchange/archive/2008/09/26/3406344.aspx




Continuing our “walk” in the XML log, we can see additional parts of information.

3. AD (number 3)

Under the <AD> XML tag, we can see the name of the DC server that serves as a

“source of information” for the Exchange server list.

As mention before, in On-Premise Active Directory environment, the Autodiscover

client will try to connect to the local Active Directory and use an LDAP query asking

to available Autodiscover Endpoints (Exchange CAS server\s).

In our scenario the DC name who provides the client the required information is –

DC01.o365info.local

4. Exchange web services (number 4) – this is the section that includes information

about all the available Exchange web services.








When using the XML format, a “dedicated tag” is allocated for each of the Exchange

services. For example:

The <ASUrl> tag is used for “holding” the URL address for Exchange available

service (Free/ Busy time).

The <EwsUrl> tag is used for “holding” the URL address of – Exchange Web

services

Saving the test results

The Outlook Test E-mail AutoConfiguration is not included by default an option for

saving the information from the test results.

In case that we want to save the content of the Autodiscover response, we can

bypass this limitation by copy the information to a Text editor such as – notepad.








In the XML tab, choose all the content by using the CTRL+ A keyboard key

combination, and then use the CTRL+ C keyboard key combination to copy the

data.

Open a notepad and paste the information.

To be able to read the information more comfortably, we will save the information

as an XML file.

Save the file name using any name whom you prefer, but it’s important to use the

.xml suffix in the file name.

In the Save as type box, use the option of – All Files

In the following screenshot, we can see an example in which we use an advanced

TXT editor such as Notepad++ for displaying the content of the XML file that we

saved in the former section.

Tip – Outlook Test E-mail AutoConfiguration , creating a

demo Outlook profile








1. The user credentials

The tool of “Outlook Test E-mail AutoConfiguration” is not depended on by the user

who is logged-in at the current time to the Outlook mail profile.

For example, in case that in the current time, the user who is logged in to the

Outlook mail profile is – [email protected] , we can use the “Outlook Test E-mail

AutoConfiguration” for testing the Autodiscover process of other recipients named

– [email protected]

2. Using the Outlook Test E-mail AutoConfiguration interface

In a scenario in which, for some reason, we cannot create a new Outlook mail

profile, technically; we cannot use the Outlook Test E-mail

AutoConfiguration because, the “activation” of this option, is from Outlook mail

profile (the chicken and the egg syndrome).

In this case, in case that we want\need to use the option of –

Outlook Test E-mail AutoConfiguration, we can use a little trick.

Instead of connecting to the Exchange server using the standard Outlook protocol

such as RPC, we can bypass this challenge by creating a new POP\IMAP mail profile

using “non-existing mail servers” the purpose is just to create a temporary Outlook

mail profile that will enable us to use the feature or the option of “Outlook Test E-

mail AutoConfiguration”

We will start to create a new Outlook mail profile and choose the option of “manual

settings” (Manual setup or additional server types).








On the next screen, we will choose the option of -POP or IMAP.








In the details box such as incoming mail server or E-mail address, you can put any

details that you want.








The final result will be a demo Outlook mail profile that is not connected to a “real

mail server” but the option of Outlook built-in tool – the Test E-mail

AutoConfiguration.





Documents

Outlook Test E-mail AutoConfiguration | Autodiscover troubleshooting tools | Part 1#4 | Part 21#36