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Page 1 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

Hybrid deployment in Office 365 |


Checklist and pre requirements | Part
2/3

The following article is part 2 of the Hybrid configuration checklist and prerequirements article series.
In the following article, we review the additional components that are involved
and relate to the Hybrid environment:

Exchange on-Premises server EWS services


Exchange on-Premises server AutoDiscover services
Exchange on-Premises server and Public Certificate

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

Page 2 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

Hybrid deployment in Office 365 | Checklist and pre -requirements |


The article series
The article series includes the following articles:

Hybrid deployment in Office 365 | Checklist and pre requirements | Part 1/3
Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3
Hybrid deployment in Office 365 | Checklist and pre requirements | Part 3/3
7. Exchange On-Premise Hybrid server | Autodiscover service
The Autodiscover service serves as a foundation for the Hybrid relationships
between the Exchange On-Premise and the Exchange Online and vice versa.
Autodiscover service will be used for the first-time configuration of the Hybrid
environment (when using the HCW) and for ongoing communication between the
On-Premise and the cloud environment.
For this reason, it is very important to verify and check the following sections that
relate to the Autodiscover services:
1. Autodiscover record and Public Network
We will need to verify that the Autodiscover record for the organization public
domain is published and pointing to Exchange On-Premise server.
The Autodiscover record is based on a reserved naming convention that is
implanted in the following way: Autodiscover.
For example- the Autodiscover record for the public domain o365info.com is:
Autodiscover.o365info.com
We will need to check and verify that the Autodiscover record was published
correctly and that the Autodiscover record is point to the Exchange On-Premise
server
In the following diagram, we can see a description of the Autodiscover process.
In our example, Exchange Online needs to get information about
o365info.com organization.
To get the required information, Exchange Online access a public DNS and query
about the Autodiscover.o365info.com record.

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

Page 3 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

In case that the Autodiscover DNS record is configured correctly, the DNS provides
the Public IP and, Exchange Online use this IP for contacting the Exchange OnPremise Autodiscover services.

Note In this section we relate only to the DNS settings for the Autodiscover service
and the rest of the section, we review other aspects the Autodiscover service that
we need to verify and check.
Autodiscover DNS record | A record
In a hybrid environment, the Autodiscover should be implemented as an A record
that is published trough the Public DNS server.
In some scenario, the Exchange On-Premise Autodiscover configuration is based on
SRV record. This scenario is not supported in Hybrid environment.
In other words: in case that the current Exchange On-Premise Autodiscover is
based on an SRV DNS record, you will need to change\update this configuration to
a standard AutoDiscover configuration that is implemented by using A record that
points to the public IP address of the Exchange On-Premise server.

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

Page 4 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

Youd also need to include these records in the SAN certificate. You could use
CNAME records for Autodiscover redirection, but that wouldnt change the fact that
you have to add all Autodiscover records to the SAN certificate. Also, Exchange
hybrid deployments dont support SRV-based Autodiscover redirection.
[Source of information: Exchange Queue & A: Handling hybrid environments ]
2. Verify successful operation of Exchange On -Premise Autodiscover
process
The fact that the Autodiscover services Record and the Public IP is published is only
the first part of the required settings. In the next step, we need to verify that we can
access Exchange On-Premise Autodiscover service + gets the required information
(Exchange On-Premise will provide the required information using an XML file).
In the following diagram, we can see that external host (such as Exchange Online)
tries to connect the local Exchange On-Premise (the AutoDiscover services of the
Exchange on-Premises server).
In case the Exchange on-Premises server respond, the Exchange Online will need
to identify and after a successful authentication, the Exchange On-Premise provides
the required information using a file named autodiscover.xml

Verify the availability of the Exchange On -Premise Autodiscover


service

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

Page 5 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

The verification of Exchange On-Premise Autodiscover service can be implemented


by using a very powerful and recommended tool named: Microsoft Remote
Connectivity Analyzer
In the following section, we review an example of the required steps that we need
to implement for verifying the availability of the Exchange On-Premise
AutoDiscover service.
1. Choose the Exchange server tab and then under the Microsoft Office Outlook
Connectivity Tests choose the option: Outlook Autodiscover

2. Provide Exchange On-Premise user credentials.


To be able to get the required information, we will need to provide user
credentials of users who have Exchange On-Premise mailbox.
In our example, we use the credentials of users named: User2

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

Page 6 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

3. In the result screen, we can see that the header is: Connectivity Test Successful
with Warning.
This is the required result, despite that the result includes a Yellow
exclamation mark. The Autodiscover test will include by default some minor
errors, that caused by the trial and error mechanism of the Autodiscover
process.
The fact that we get the Green icon is the Indication for the successful

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

Page 7 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

implementation of the Autodiscover process.

4. In case that we want to get more detailed information, we can click on the Test
Step.
In the following screenshot, we can see the content of the Autodiscover XML file.

3. Autodiscover and Exchange On-Premise server version


In a mixed Exchange On-Premise environment, that includes a couple of Exchange
On-Premise versions, we will have to verify that the Autodiscover record is
pointing to the most updated Exchange On-Premise server version.

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

Page 8 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

Technically, each of the Exchange servers since Exchange version 2007 can provide
Autodiscover services, but the why that Exchange server prepare the required
data (the XML file), and the content of the Autodiscover file, is created and
implemented in a different way in each of the Exchange server versions.
In a mix Exchange environment, the backward computability concept is
implemented.
The latest Exchange server version can get queries for AutoDiscover information
and understand how to format the required answer.
For example, in case that we point the Autodiscover record to the Exchange 2013
server, and external client asks for the Free\busy time of a recipient (Availability
services) who is hosted on the Exchange 2007 server, the Exchange 2013 knows
how to format the request and the answer that is sent from the Exchange 2007
server in a proper way.
4. Autodiscover record pointing to the Exchange On -Premise server
One of the most common mistakes related to Autodiscover record and Hybrid
implementations is: updating the Autodiscover record to point the cloud
(autodiscover.outlook.com).
This assumption may seem logic, but this update should not be implemented.
In a Hybrid configuration, the Autodiscover record that represent the Public
domain name should point to the Exchange On-Premise server.

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

Page 9 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part 2/3

Note we dont need to configure or update any of the Autodiscover settings that
related to the cloud because in Office 365, all the required configurations of the
Autodiscover services are configured automatically by using the service domain or
the Tenet Office 365 domain such aso365info.mail.onmicrosoft.com

8. Exchange On-Premise Hybrid server | EWS service


The hybrid environment is based on the concept in which two separated Exchange
organization operates as one entity. For example, enable Exchange on-Premises
users to see Free/Busy time information about Exchange Online recipients, get Out
of office messages and much more.
The infrastructure for this collaboration between the Exchange on-Premises
server and Exchange Online is based on the Exchange EWS (Exchange Web
Services) service.
The meaning is that:

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

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Exchange On-Premise will have to be accessible from the public network.


Exchange On-Premise EWS services must be configured correctly.
Note the Hybrid configuration is based on a two-way relationship in which the
Exchange On-Premise will also need to access the Exchange Online EWS but the
basic assumption is that the cloud infrastructure (Exchange Online) is configured
correctly and besides of a very rare events, we assume that the cloud side allows
available and configured correctly.

Verify - check the availability of: Exchange On -Premise Hybrid server


EWS service
We can check or verify the availability of Exchange On-Premise and EWS service by
using one of the following options:
Option1: Verify\check the availability of Exchange On-Premise and EWS
service using the EWS URL
In this option, we can simply try to access the URL of the Exchange On-Premise Web
services (EWS).
The default URL is based on the following naming conversation: https:/<Exchange
public name>/ews/exchange.asmx

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

Page 11 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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In our scenario, the Public name of the Exchange On-Premise is: mail.o3655info.com
We will open a web browser and use the following URL
address:https:/mail.o365info.com/ews/exchange.asmx
In the following screenshot, we can see that we can successfully connect the EWS
services of the Exchange On-Premise.
As a response, Exchange on-Premises server sends a requirement for
authentication.
Additionally, we can see that the server certificate is proper because the Lock icon
has no errors.
The credentials that we will need to provide are just a simple user credential of any
recipient who has a mailbox on the Exchange On-Premise server.

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

Page 12 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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The Exchange On-Premise answer is an XML file that includes the required
information or description about the Exchange On-Premise Web Services.
There is no actual meaning for us. The only meaning is that we could access the
Exchange On-Premise EWS service and get the Exchange server response.

Option 2: Verify\check the availability of Exchange On-Premise and EWS


service by using the Exchange remote connectivity analyzer
The Verification of Exchange On-Premise EWS service can be implemented by using
a very powerful and recommended tool named: Microsoft Remote Connectivity
Analyzer
In the following screenshot, we can see an example of the required steps that we
need to implement for verifying the availability of the Exchange On-Premise EWS
service.

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

Page 13 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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1. Choose the Exchange server tab and then under the Microsoft Exchange Web
Services Connectivity Tests choose the option: Synchronization, Notification,
availability and Automatic reply

2. Provide Exchange On-Premise user credentials


To be able to get the required information, we will need to provide user credentials
of users that have Exchange On-Premise mailbox.
In our example, we use the credentials of users named: User2

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

Page 14 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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3. In the result screen, we can see that the header is: Connectivity Test Successful
with Warning.
This is the required result despite that the result includes a Yellow Exclamation
mark.
The Exchange On-Premise Web service test will include by default some minor
errors that caused by the trial and error mechanism of the AutoDiscover process.
The fact that we get the Green icon is the Indication for the successful
implementation of the Exchange On-Premise Web service process.

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

Page 15 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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4. In case that we want to get more detailed information, we can click on the Test
Step.
In the following screenshot, we can see the content of the AutoDiscover XML file.

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

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Additional reading

Exchange Web Services Architecture


Exchange Web Services (EWS)

9. Exchange On-Premise Hybrid server | Public


Certificate
The communication channel between the Exchange Online and Exchange OnPremise, is based on the basic assumption that the communication channel is
secured. The need for securing the communication channel, is because the fact
that the information between the two endpoints is transferred over the public
network.
The creation of the secure communication channel is implemented by using a
secure protocol such as HTTPS and SMTP\TLS and the component that is used for

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

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creating data encryption. Data integrity, mutual authentication and so on, is based
on a Public certificate that is the use of both sides (Exchange Online and Exchange
On-Premise).
The basic assumption is that the Exchange Online Public certificate is configured
correctly and available.
In our scenario, we will need to verify the subject of the Public certificate on the
Exchange On-Premise server side.
Note we will not get into details about how to create a certificate request install a
public certificate on the Exchange On-Premise and so on.
The basic assumption is that the Exchange On-Premise includes an insulation of
Public certificate, and we just want to verify that the Public certificate is installed
and include the required information.
The Exchange On-Premise public certificate will be used as part of the AutoDiscover
service and actually for the encryption of the mail flow (SMTP/TLS) between the
Exchange On-Premise server and Exchange Online server.
In the following diagram, we can see an example for the Hosts names that will
need to be included in the Exchange On-Premise public certificate.
In our scenario, the Exchange On-Premise public certificate should include the
hosts name:Autodiacover.o3655info.com for the Autodiscover services and
additional hostname mail.o3655info.com
this is the host name which will be used by Exchange Online server for addressing
Exchange On-Premise server (creating a secure communication channel to the
Exchange On-Premise server).

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

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Public certificate types


There is a couple of Public certificate types. The most common types are:
Wildcard certificate and SAN (Subject Alternative Name) certificate.
The major difference between this two type is: that the wildcard certificate doesnt
include information about a specific hosts name versus the SAN certificate that
need to include a specific name of the Host that are allowed to use the certificate.
Public certificate requirements
To be able to check\verify the Public certificate setting in Exchange On-Premise, use
the Exchange MMC, Server configuration, choose the Hybrid server name (EX01 in
our scenario) by looking at the Exchange Certificate Tab.
Note these instructions are relevant for the Exchange 2010 interface.

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

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There are three main requirements that relate to the Exchange On-Premise
certificate:
1. Public certificate
The meaning of the term Public certificate is that the certificate was created by a
Public CA (Certificate Authority).
In the following screenshot, we use the Exchange 2010 On-Premise MMC interface
for getting information about the Public certificate.
We can see that under the section of self-Signed, the value of the certificate is:
False (number1 in the screenshot).
The meaning is that this certificate was not created by the Exchange On-Premise
server (self- Signed but instead was created by a Public Certificate provider.
2. Certificate assignment

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

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The Public Certificate should be assigned to the following Exchange services: IIS and
SMTP (number 2 in the screenshot).

3. SAN Public certificate


An SAN (Subject Alternative Name) certificate includes that name of the hosts who
allowed to use the certificate.
The term Subject described the Host name who could be implemented as a
simple host name such as: SRV1 or FQDN such as: mail.o3655info.com
When Exchange on-Premises server present his public certificate to Exchange
Online, Exchange Online will need to check, that the mail server name who was
configured in the Exchange Online receives connector, is included in the Public
certificate that the Exchange on-Premises server provide.
(In our scenario: the Public certificate that Exchange on-Premises server provider
will need to include the hostname: mail.o3655info.com.
We recommend that you provide all the necessary DNS names in the same
certificate by using a Unified Communications certificate that supports the Subject
Alternative Name field. Using a Unified Communications certificate reduces the
complexity of configuring and managing the Autodiscover service and Exchange
services URLs. However, using a Unified Communications certificate may increase
the cost, as this kind of certificate can be more expensive than the single-name
certificates that you already may own.
[Source of information: White Paper: Understanding the Exchange 2010
Autodiscover Service ]
Verify-Check the content of the Exchange on -Premises server Public
certificate

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

Page 21 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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Option 1: get information about the Pubic Certificate using Exchange MMC
To be able to verify the hosts named that are included in the Public certificate,
double-click on the public certificate and on the details tab look for the field
Subject Alternative Name
In the following screenshots, we can see that the public certificate includes all of the
required hosts names.

Note the subject of including hosts names in a Public certificate is not relevant
when we use a wild-card certificate because in this scenario, the certificate relates
to all the of the hosts under a specific domain.

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

Page 22 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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Option 2: check the Exchange On-Premise Public certificate by access the


OWA URL
Another option to check the Exchange On-Premise public certificate is to access the
Exchange On-Premise URL that is used for the OWA access.
In our scenario, the OWA URL is: https://mail.o365info.com/owa
In the following screenshot, we can see that we use the URL, on the right corner of
the URL Bar, we can see the lock icon that represents the fact that the site provides
a certificate.
When we double-click on the lock icon, we will be able to see the content of the
public certificate that the Exchange on-Premises server provides.

10. Microsoft MFG server and the proof of the ownership process
The first step when we need to create a Hybrid configuration is the step in which
the Exchange On-Premise server creates trust relations with the Microsoft
Federation gateway (MFG).
This trust relationship described as Federation trust
Note when using hybrid configuration both of the sides (Exchange On-Premise
and Exchange Online) need to trust the MFG. The Office 365 cloud infrastructure

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is set to automatically trust the MFG server so the only requirement is to build a
new trust between the Exchange On-Premise and MFG.

The creation of the Federation trust with the Microsoft MFG server, is created by
implementing a proof of ownership process for the public domain that we use.
For example: in case that we want to configure Hybrid configuration using the
public domain name: o3655info.com, we will need to prove that we own this
domain.
The proof of ownership process is implemented in the following way: when using
the HCW, Exchange On-Premise contacts the Microsoft MFG server.
The MFG server reply with a TXT string.
We will need to copy this text string, go to our public DNS server, add a new TXT
record that includes the value that was provided by the MFG server and only after
we have created the proof, MFG servers will access our public DNS server looking
for this TXT string.

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

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In the following diagram, we can see a description of the flow or the steps that are
required for building the trust with the Microsoft MFG server.

When using the HCW (Exchange Hybrid configuration wizard), the required TXT
string that sent from the MFG server will be displayed on the screen.
In case that for some reason the required TXT string is not displayed, we can use a
PowerShell command for displaying the TXT string (the TXT Domain Proof).
The PowerShell that we use is based on the following syntax:
PowerShell
1 Get-FederatedDomainProof -DomainName "<Domain name>"
In the following screenshot, we can see the Domain Proof Text string.

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

Page 25 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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Option 1: Verify that the TXT record is configured correctly in the Public DNS
using a Nslookup command tool
In case that we want to verify that the TXT record (TXT Domain Proof) was
configured correctly in the Public DNS, we can create a query for a TXT record.
To verify that the TXT record (TXT Domain Proof) was configured in the Public DNS,
you can check the information by using the NSLOOKUP command.
For example we can use the NSLOOKUP tool for getting information about the
TXT record that are configured in the domain: o3655info.com
from the command prompt we type:
Nslookup
Set type=txt
Next we will type the name of the domain name which we want to query.
o365info.com
In the following screenshot, we can see the result of the Nslookup command

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

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Option 2: Verify that the TXT record is configured correctly in the Public DNS
using web tool.
There are many free web tools that can help us to check and query DNS server.
In the following example, we will use the site: mxtoolbox
1. Choose the More menu

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

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2. Choose the TXT option and type the domain name that you want to query.

3. In our example, we would like to get information about all the TXT records in the
domain o365info.com
In the following screenshot, we can see the result of the query. There is a two
TXT record under the o365info.com domain.
One of this TXT record is the Text string that was provided by the Microsoft MFG
server and was updated in the o365info.com domain as a TXT record.

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

Page 28 of 32 | Hybrid deployment in Office 365 | Checklist and pre requirements | Part
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11. Direct communication channel | Exchange onPremises server to Exchange Online


The subject of mail flow in Hybrid configuration relates to many scenarios of:
incoming and outgoing mail flow, such as: mail that sends from cloud
infrastructure (Exchange Online to a public network), mail that sent from Exchange
on-Premises server infrastructure to a public network, mail that is sent from the
public network to the organization domain (the MX record could point to the
Exchange on-Premise server or to the Exchange Online server) and so on.
We will not get into details of all the available mail flow scenario, but instead, I
would like to emphasize only the mail flow between the Exchange on-Premises
server and the Exchange Online and vice versa.
As mentioned before, in Hybrid configuration the Exchange on-Premises server and
Exchange Online, act as one unit or one entity.
The configuration is implemented by creating a direct communication path
between the Exchange on-Premises server and Exchange Online that is based on
SMTP\TLS and HTTPS protocol.
All the mail flow between Exchange on-Premises server and Exchange Online is
passing through this secure communication channel.
For example: in case that Bobs mailbox is located on the Exchange on-Premises
server and, Bob send mail to Alice that her mailbox is located on the Exchange
Online server, the mail will be transferred by the Exchange on-Premises server to
the Exchange Online by using the direct secure communication link that exists
between Exchange on-Premises server and Exchange Online (this secure channel
is created by the HCW Exchange Hybrid configuration wizard)

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In the following diagram, we can see an example for the required configuration for
the secure communication link between the Exchange On-Premise and the
Exchange Online server.
In our scenario, the shared domain is o365info.com
Each of the mail that will be sent from Exchange On-Premise recipient to cloud
recipient (Exchange Online) and vice versa, that include the domain name:
o365info.com, will be routed through the direct secure communication channel that
exists.
Note the direct secure communication channel is implemented by a set of four
connectors:
1 send connector, and 1 receive connector that created on the Exchange OnPremise hybrid server and the same on the Exchange Online side.

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

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Another supported scenario could be a scenario in which the Exchange On-Premise


environment includes an Edge transport server. In this scenario, the direct secure
communication channel will be created by using the Edge transport server as an
end-point or gateway on the On-Premise side.

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

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A non-supported scenario | using non-Exchange server as On-Premise


End-point
A non-supported scenario that we need to avoid is: a scenario in which we use
non-Exchange server as an endpoint in the On-Premise environment.
For example: in the following diagram, we can see a scenario in which the direct
secure communication channel was created between a mail security gateway (nonExchange server) and Exchange Online.
Technically speaking, we can implement this scenario, but this configuration is not
supported, and there is a Reasonable chance (if not a certain chance) that you will
experience many types of problems.
The reason that this scenario is not supported because the direct secure
communication channel in a hybrid environment is not just a simple connector
between two separated mail servers, but instead, a communication channel that
includes many configuration settings and parameter that relate directly to
Exchange servers

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There can be no other SMTP hosts or services between the on-premises


Exchange 2013 Client Access servers or an Exchange 2013/2010 SP3 Edge
Transport server and EOP. Information added to messages that enables hybrid
transport features is removed when they pass through a non-Exchange 2013
server, pre-Exchange 2010 SP3 servers, or an SMTP host.
[Source of information: Transport Options in Exchange 2013 Hybrid Deployments ]
Additional reading

Hybrid deployment best practices


Exchange Online Protection, Mailflow, and Encryption: Notes from the Field
Automated Hybrid Troubleshooting Experience
Office 365 Common Exchange Online Hybrid Mail Flow Issues
You Cannot Send or Receive E-Mail Messages Behind a Cisco PIX Firewall

Video links

Support Webcast, Troubleshoot Mail Flow for Hybrid Cloud Environment


Support Webcast, Understanding and troubleshooting Exchange Hybrid
(Federation and OAUTH)

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

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