Microsoft connectivity analyzer (mca) autodiscover troubleshooting tools part 3#4 part 23#36

of 20 | Microsoft Connectivity Analyzer (MCA) | Autodiscover troubleshooting tools
| Part 3#4 | Part 23#36
Written by Eyal Doron | o365info.com | Copyright © 2012-2015
Microsoft Connectivity Analyzer (MCA)
| Autodiscover troubleshooting tools |
Part 3#4 | Part 23#36
The Microsoft Connectivity Analyzer (MCA) tool is the “installable client” or the
“software client” version of the ExRCA (Microsoft Remote Connectivity Analyzer
Tool) Autodiscover test.
The main purpose of using the Microsoft Connectivity Analyzer (MCA) tool versus
the Microsoft Remote Connectivity Analyzer web Tool is the ability to test the
Autodiscover process from inside the organization’s network or by testing the
Autodiscover process from a specific user desktop.
Autodiscover Troubleshooting tools | The article series

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The article series include the following articles:
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
ExRCA (Microsoft Remote Connectivity Analyzer Tool)
When using the ExRCA (Microsoft Remote Connectivity Analyzer Tool) web-based
tool, we are acutely using and external public server who uses for simulating the
Autodiscover flow.
In reality, the Autodiscover communication channel can be implemented from the
internal private organization network or from a public network.
The important issue is that the way that the Autodiscover channel is implemented
in a scenario of private organization’s network versus external public network is
different because different components are involved in the Autodiscover process.
An additional important observation regarding the Microsoft Connectivity Analyzer
(MCA) toll is – that although this tool is installed on the user desktop, the Microsoft
Connectivity Analyzer (MCA) tool cannot use for checking or using the Autodiscover
method which is implemented in an Active Directory-based environment.
In other words, we cannot use the Microsoft Connectivity Analyzer (MCA) tool for
testing the Autodiscover LDAP method in which the Autodiscover client addresses
the local Active Directory.

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MCA advantages and disadvantages
Advantages
 The Microsoft Connectivity Analyzer (MCA) serves as an Autodiscover and
enables us to inspect and analyze the Autodiscover and Outlook Anywhere
flow with Outlook the need of installing a mail client such as Outlook.
 The Microsoft Connectivity Analyzer (MCA) enables us to simulate the
Autodiscover process by executing the Autodiscover process from a specific
host and a specific network versus the ExRCA tool that is implemented by
using a Microsoft public server.
Disadvantages
 The Microsoft Connectivity Analyzer (MCA) client cannot monitor and inspect
the Autodiscover in an Active Directory environment (the Autodiscover based
on the LDAP query, etc.).
 The Microsoft Connectivity Analyzer (MCA) doesn’t include all the options that
include when using a tool such as the ExRCA.
 The Microsoft Connectivity Analyzer (MCA) toll considers as a software that we
download + install versus the ExRCA tool that is a web-based tool.
Microsoft Connectivity Analyzer (MCA) versus ExRCA
(Microsoft Remote Connectivity Analyzer).

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1. Software component versus web application
The most noticeable difference between the Microsoft Connectivity Analyzer (MCA)
and the ExRCA (Microsoft Remote Connectivity Analyzer) is that the MCA is a
software component which we need to install versus the ExRCA that is
implemented as a web application (Using the ExRCA is implemented by accessing
the ExRCA URL etc.).
2. Restricted number of “tests” options
An additional difference is that we can relate to the Microsoft Connectivity Analyzer
(MCA) as a “minimized version” or a limited version that offers only a restricted set
of “tests” compared to the option that are available when using the Remote
Connectivity Analyzer Tool.
3. User interface
The user interface of the Microsoft Connectivity Analyzer (MCA) is different from the
ExRCA (Microsoft Remote Connectivity Analyzer).
Versus the Microsoft Remote Connectivity Analyzer that is based on the concepts of
“tabs” and a list of optional tests that the user can choose from, the MCA (Microsoft
Connectivity Analyzer) interface is on a “wizard-based” interface.
The user chooses the description if the problem that he experiences and, based on
the “user section” the Microsoft Connectivity Analyzer (MCA) offers the most
appropriate test.
4. Integrated test implemented – Autodiscover + Outlook Anywhere.
As part of the simplified user interface, the MCA (Microsoft Connectivity Analyzer)
combines two separate tests into one.
When a user reports that he cannot create a new Outlook mail profile the problem
could be related to the Autodiscover infrastructure or to the Outlook Anywhere
sitting on the server side.
In the previous article (Microsoft Remote Connectivity Analyzer (ExRCA) |
Autodiscover troubleshooting tools | Part 2#4 | Part 22#36) we review the ExRCA
interface and the option of choosing a “dedicated” Autodiscover test.

| Part 3#4 | Part 23#36
Versus this option, the MCA (Microsoft Connectivity Analyzer wizard offers the user
to choose an option named – “I can’t log on with office Outlook”.
In case that the user selects this option, the MCA will perform two different tests at
the same time – the Autodiscover test + the Outlook Anywhere (RCP/HTTPS) test.
General notes about the MCA interface
My opinion or wish is that – the user interface should have designed differently and
provide an interface that is similar or even identical to the Remote Connectivity
Analyzer Tool.
I hope that in future, somebody will read what I have written and adapt my
recommendations (yes, I know that I live in a la la land; -))
Download and install the MCA (Microsoft Connectivity Analyzer)
software component.
Go to the -Microsoft Remote Connectivity Analyzer
(https://testconnectivity.microsoft.com/) site and, choose the Client tab and click on
the Install now option.
MCA – requirement for installation
The requirement for installation MCA (Microsoft Connectivity Analyzer) on a
desktop are:

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 The tool supports the following operating systems: Windows Vista, Windows 7,
Windows Server 2008, Windows 8
 Microsoft .NET Framework 4.5 is required
Using the MCA (Microsoft Connectivity Analyzer)
To demonstrate the use of the use of the MCA (Microsoft Connectivity Analyzer), we
will use the following scenario:
A user named John that uses the E-mail address – John@o365info.com , what to
create a new Outlook mail profile.
John desk is a domain joined and, John is located in the private company network.
Note – Don’t forget that the MCA (Microsoft Connectivity Analyzer) doesn’t know
how to use the Active Directory Autodiscover method and the MCA (Microsoft
Connectivity Analyzer) can only use the Autodiscover method that is implemented
in a non-Active Directory environment.
We would like to review the Autodiscover workflow that is implemented between
the Autodiscover client and the Autodiscover Endpoint.

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Step 1- Choosing the required test
To be able to perform the Autodiscover test, we will need to choose the option – “I
can’t log on with office Outlook”.
Note – In case this option is selected the MCA will perform two tests at the same
time -the Autodiscover test + the Outlook Anywhere (RCP/HTTPS) test.
Step 2- Providing user credentials
In case that we use an Exchange on-Premises server infrastructure, most of the
time the authentication naming convention will be based on the “formula” of –
<Doman name><User name>

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Step 3- viewing or saving the test results
After the test is completed, we can choose one of the following options:
Viewing the test results or saving the test results.

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Analyzing the content of the test results
In the following screenshot, we can see that the test result completes successfully,
but it’s important to notice that the test was implemented by using two different
Exchange services:
1. Autodiscover infrastructure test
2. Outlook Anywhere infrastructure (RPCHTTPS) test
In our scenario, we can see that both of this test were completed successfully.
The result’s screen is divided into two parts:
1. General summary of the test results (Part A in the screenshot)

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2. A detailed report about each of the operations that was included in the test
(Part B in the screenshot)

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The MCA (Microsoft Connectivity Analyzer) result is display based on the same
hierarchical concept that is used by the ExRCA tool.
The “top level” result can be “expanded” so we can see each of the “steps” that were
involved in a specific test and most of the time, we also have the ability to “expand”
each of the specific steps to get more detailed information.
Part B.1 – analyzing the Autodiscover test results
Step 1: Trying to connect the Autodiscover Endpoint host using the Root domain
name
In the following screenshot, we can see that the Autodiscover process in non-Active
Directory environment is implemented by using the recipient E-mail address,
domain name and then, using the domain name as a potential Autodiscover
Endpoint host name.

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In our scenario, although the host manage to resolve the hostname to IP address,
when the Autodiscover client tries to verify if the potential Autodiscover Endpoint
can communicate using HTTPS, the test fails (number 1).
Step 2: Trying to connect the potential Autodiscover Endpoint using the
Autodiscover standard host name
In the following screenshot, we can see that the Autodiscover client “move on” to
the next host name option in which he will try to look for the potential Autodiscover
Endpoint using the naming convention: Autodiscover + recipient SMTP domain
name.
In our scenario, the potential Autodiscover Endpoint will be
– autodiscover.o365info.com
We can see that the steps of: Resolving the host name to IP and Verify the potential
Autodiscover Endpoint can communicate using HTTPS complete successfully
(number 2).

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Looking at the details of the Autodiscover test
To be able to get more detailed information about the specific steps that was
implemented and a full description of the results for each if this step, all we need to
do is just double-click on the “expand icon” that appear to the left of the
Autodiscover method title
(attempting to test Potential Autodiscover URL
https://autodiscover.o365info.com/Autodiscover/autodiscer.xml)
In the following screenshot, we can see the “headers” of the five steps that were
implemented by the Autodiscover client
Step 1 – Attempting to resolve the host names autodiscover.o365info.com
Step 2 – testing TCP port 443

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Step 3 – Testing the SSL certificate
Step 4 – Checking the IIS configuration for client certificate authentication
Step 5 – attempting to send an Autodiscover Post request to the Potential
Autodiscover URLs
The End of the Journey – the client gets the required Autodiscover.xml file
In the following screenshot, we can see that the Autodiscover client sends to the
Autodiscover Endpoint a request:
attempting to send an Autodiscover POST request to Potential Autodiscover URLs.

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The Autodiscover Endpoint generates the required information and sends it to the
Autodiscover client. We can see that the content of the information includes the
data in an XML format.
The Autodiscover server response includes the URL address of the different
Exchange web services such as – Availability services, OOO and so on.
Part B.2 – analyzing the Outlook Anywhere test results
The next part of the MCA (Microsoft Connectivity Analyzer) result relates to the
Outlook Anywhere service (or the former name RPC/HTTPS).
In case that the mail client needs access from an external network, the
Autodiscover serves as infrastructure for the Outlook Anywhere services.
Only when the first part of the Autodiscover process will be successful completed,
then the “second part” of Outlook Anywhere can be also completed.

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We will not go into a detailed review of the Outlook Anywhere service test results,
but it’s important to understand that the Outlook Anywhere includes a complete set
of “steps” that need to be implemented.
In case that we want to view a detail report of the Outlook Anywhere results, we
need to expand the required section.
In the following screenshot, we can see all the steps that are involved in an Outlook
Anywhere communication channel.
For example, we can see that the Outlook Anywhere client is “talking” with the
internal name of the Exchange On-Premise server, by using the host name
– exo1.o365info.lcoal (number 5).

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The Outlook Anywhere “journey” is not finished it!
In following screenshot, we can see the “reset” of the steps that are implemented
by the Outlook Anywhere client.
For example, the Outlook Anywhere client will try to “RPC ping” the RPC Proxy
server. In our scenario, the RPC proxy server name is
– mail.o365info.com (number 6).

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Saving the test results
In case that we want to save the report for additional analyses, we can save the
report to an HTML file.
In the report result choose the option of- save results.

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In the HTML result file, we can see the report information.
The upper part includes a general summary and on the bottom part we can use,
the expand button to get a detailed overview about each of the steps that was
implemented.

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Additional reading
 Announcing Microsoft Connectivity Analyzer (MCA) 1.0 and Microsoft Remote
Connectivity Analyzer (RCA) 2.1
 What’s new with Microsoft Remote Connectivity Analyzer? A lot!
Video link
 Microsoft Connectivity Analyzer Introduction

Microsoft connectivity analyzer (mca) autodiscover troubleshooting tools part 3#4 part 23#36

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