The current article and the next article, will be dedicated for detailed review of the
Autodiscover flow, that is implemented in an Office 365 based environment by
using the Microsoft web-based tool, the Microsoft Remote Connectivity Analyzer
(ExRCA).
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2. There are many moving parts and many passable paths for the Autodiscover
journey.
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3. Part of the Autodiscover process includes built-in failures. This failure are
normal and expected. What matters is the final results meaning did the
Autodiscover client manage to successfully complete the Autodiscover journey
or not.
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The default assumption of the Autodiscover client is that each of these elements
is the required Autodiscover Endpoint (potential Autodiscover Endpoint).
In reality, only the last node is the truth Autodiscover Endpoint. All the rest of the
hosts who involved in the Autodiscover process in an Office 365 environment, serve
as a logical routers that will lead and redirect the Autodiscover client to his
destiny.
3. The purpose of the Journey
The only purpose of the Autodiscover Journey is very simple to get an
Autodiscover response that includes the required configuration setting for a new
Outlook mail profile + infrastructure about existing Exchange web services.
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Before we will get into the details, is important that we will be able to see the big
picture or the major nodes that will participate in the Autodiscover journey in
Office 365 and Exchange Online environment.
In the following diagram, we can see the Autodiscover client will have to pass
through many nodes in his journey, before he is able to complete the Autodiscover
journey and get to his final destination (number 4 in the diagram).
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Scenario description
To be able to demonstrate the Autodiscover process in a cloud only environment,
we use the following scenario:
An organization named o365info.com, use Office 365 and the Exchange Online as
their mail infrastructure. All the users mailboxes are hosted at the Exchange Online
infrastructure.
In our scenario, a user named Bob that uses the following E-mail address
Bob@o365info.com, needs to create a new Outlook mail profile.
The Autodiscover client will start his Autodiscover journey, by looking for an
Autodiscover Endpoint named o365info.com
The Autodiscover Endpoint uses this specific hostname because the Autodiscover
Algorithm is based on a method in which the Autodiscover client is taking the
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In the following screenshots, we can see the results of the Outlook Autodiscover
process for bobs mailbox that is hosted on the Exchange Online.
In this high level view of the Autodiscover test results, we can clearly see the
structure of the Autodiscover process that is implemented in the Office 365
environment.
(The Autodiscover process is implemented in a different way than a standard
Autodiscover process of external client that tries to access Exchange On-Premise
infrastructure).
The first two steps, in which the Autodiscover client tries to access the standard
Autodiscover Endpoint by using the host names o365info.com and,
autodiscover.o365info.com failed (number 1 and 2 in the screenshot).
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The real Autodiscover process in an Office 365 environment start only after the
phase of the HTTP redirection that is implemented by the element named
autodiscover.o365info.com(number 3 in the screenshot).
When we look at the Autodiscover process that is implemented in the Office 365
environment, we can see that the Autodiscover client will be redirected to
additional Office 365 elements named Autodiscover-s.outlook.com (number 4 in the
screenshot).
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When the Autodiscover client reaches the Office 365 elements namedAutodiscover-s.outlook.com, he will be redirected again to his final destination the
Exchange Online CAS server who will connect the mail client to his mailbox,
provide him the required Autodiscover information, etc.
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(We will get more details about the reason for the failure in the next section)
Note that when we look at the details of the Autodiscover flow that was performed
by the Autodiscover client, we can see that some of the steps to complete
successfully.
For example, the name resolution step, in which the Autodiscover client asks for the
DNS server the IP address of the host o365info.com complete successfully.
Attempting to resolve the host name o365info.com in DNS. The host name resolved
successfully. IP addresses returned: 104.28.12.85, 104.28.13.85
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Step 2/20: Analyzing the data from the ExRCA connectivity test
In the ExRCA result page, we can see the following information about the process in
which the Autodiscover client tries to verify of the destination host
(o365info.com ) can communicate using TCP port 443
The specified port is either blocked, not listening, or not producing the expected
response. A network error occurred while communicating with the remote host.
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Step 3/20: Analyzing the data from the ExRCA connectivity test
In the ExRCA result page, we can see the following information about the
Attempting to resolve the host name autodiscover.o365info.com
The host name resolved successfully. IP addresses returned: 157.56.236.89,
157.56.234.137, 157.56.232.9, 157.56.244.217
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Step 4/20: Analyzing the data from the ExRCA connectivity test
In the ExRCA result page, we can see that the HTTPS communication test with the
destination Autodiscover Endpoint (autodiscover.outlook.com) fails.
Testing TCP port 443 on host autodiscover.o365info.com to ensure its listening and
open. The specified port is either blocked, not listening, or not producing the
expected response. A network error occurred while communicating with the
remote host.
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described as
HTTP redirect request.
The Autodiscover client check of the destination host is listed to communication
through HTTP (Port 80).
In our scenario, the destination host answers to the HTTP communication request.
The positive response from the destination host is telling to the Autodiscover
client that this is probably an element that can help him by providing the name of
an additional host who serves as Autodiscover Endpoint.
In the next step, we will see how the Autodiscover client will send an HTTP query
that includes a request for an alternate host name and URL that can provide the
required Autodiscover services.
Step 5/20: Analyzing the data from the ExRCA connectivity test
In the ExRCA result page, we can see the following information about the
Attempting to contact the Autodiscover service using the HTTP redirect method:
The Autodiscover service was successfully contacted using the HTTP redirect
method.
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Step 6/20: Analyzing the data from the ExRCA connectivity test
On the ExRCA result page, we can see the following informationThe redirect (HTTP 301/302) response was received successfully. Redirect URL:
https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml
Additional reading
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