Module 18

Exchange Online
Hybrid Coexistence
Presenter name
Presenter role

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Overview

This module will cover the Hybrid Deployment model that is

available to customers already running Exchange on-premises,
including:
Overview of a Hybrid Deployment
Hybrid Deployment Implementation and Architecture
Mailbox Migrations

Objectives

After completing this module, you will be able to:

Plan for a hybrid deployment
Understand the Exchange Federation Trust and Organization
Relationships
Run the Hybrid Configuration Wizard
Understand the various Hybrid mail flow scenarios
Perform mailbox moves to Office 365
Off-board Mailboxes back to on-premises
View cross premises free/busy data

Overview of a
Hybrid
Deployment

What is a
Hybrid
Deploymen
t

A hybrid deployment is created between an on-premises

Exchange organization and Exchange Online
It provides a seamless look and feel of a single organization
Offers near-parity of features/experience on-premises and
online
Enables cross-premises calendaring, smooth mailbox
migrations, and easy off-boarding
Administrators can manage both environments from one
location using the Exchange Administration Centre (EAC)

Hybrid
Deploymen
t Benefits

Federation Trust

Delegated authentication between on-premises

and Exchange Online Web services
Enables Free/Busy, calendar sharing, message
tracking, online archive and more

Integrated
Admin
Experience

Manage all of your daily Exchange tasks, be it onpremises or in Exchange Online, from one central
location, the Exchange Admin Center

Native Mailbox
Move

Online mailbox moves

Preservation of the Outlook profile and OST file
Leverages the Mailbox Replication Service (MRS)

Secure Mail
Flow

Authenticated and encrypted mail flow

Preserves the internal Exchange message headers
Support for compliance mail flow scenarios
(centralized transport)
7

Hybrid
Coexistenc
e Feature
Comparison

Hybrid
Deploymen
t
Prerequisite
s

On-premises Exchange organization (minimum E2K3 SP2)

Office 365 for Enterprises
The Azure Directory Synchronization tool
AutoDiscover DNS records configured for each SMTP domain
A certificate from a trusted third-party CA
AD FS is optional but strongly recommended

Hybrid
Deploymen
t Exchange
Requiremen
ts

Internet facing Exchange 2010 SP3 CAS/HUB/MBX if running

Exchange 2003 on-premises
Internet facing Exchange 2013 CAS/MBX if running Exchange
2007+ on-premises
Active Directory Windows Server 2003 forest functional level
or higher
Domain Controllers must be Windows Server 2003 SP2 or
higher
Global Catalogs in each site with Exchange 2013 need to be
Windows 2008, R2, or 2012
Exchange Web Services and AutoDiscover on the Exchange
2010 or Exchange 2013 Client Access Server published to the
internet (without pre-authentication) and secured with a
public certificate

10

Hybrid
Server
Roles

11

Hybrid
Deploymen
t
Limitations

Cross premises delegate permissions:

Delegate permissions are migrated by DirSync but delegate access does
not work when the delegator and delegate are split between on-premises
and online, or vice versa
Mailbox permissions:
Send-As and Full Access permissions are migrated when the mailbox is
moved through the Mailbox Replication Service
Permissions on mailboxes that reference distribution lists and mail-enabled
users are not preserved. These must be re-added using these cmdlets:
Add-RecipientPermission (for Send-As)
Add-MailboxPermission (for Full Access)
Cross premises Public Folder access:
Public Folders are now available in Exchange Online and you can choose
which sides hosts the public folder content
On-premises users must be on Exchange 2013 if you wish for them to
access Exchange Online public folders
Public folders can only exist in one location, on-premises or in Exchange
online

12

Managing
Exchange
in Hybrid
mode

EAC is your one stop shop for managing Exchange Server

2013 on-premises, your Exchange Online tenant, hybrid
settings and mailbox migrations
EAC is 100% browser based, so you can manage on-premises
and cloud from anywhere (subject to your access controls)
EAC provides a single consolidated set of Exchange
Notifications across all premises
Support for a merged recipient views for helpdesk staff
Hybrid depends on Office 365 Directory Synchronization
That means you create new Office 365 mailboxes via the onpremises Enterprise pivot within EAC and allow DirSync to
replicate the changes to Office 365

13

Hybrid Deployment
Implementation
and Architecture

14

Collaboratio
n Before
Exchange
2010

Earlier versions of Exchange had limited sharing capabilities

between organizations and were extremely complex to setup. To
share availability information with another Exchange
organization you had to:
Use the Inter-Org Replication tool to replicate public
folders between Exchange organizations
Create Active Directory trusts between both organizations, as
well as manage service account credentials
Establishing a VPN between the two organizations

With the introduction of Exchange 2007, the Exchange Web

Service and the Availability Service made the replication of
public folder free/busy data no longer necessary in order to
share Free/Busy data between organizations:
However, trust or credential information and global address
list (GAL) synchronization was still necessary to make
free/busy information available to external organizations
15

Federated
Delegation

With Exchange 2010, a new feature called Federated Delegation

allows users to share information with recipients in external
organizations by establishing a federation trust and creating
organization relationships between the Exchange 2010
organizations
Once in place, authenticated requests between servers on
behalf of users allows access to certain features across multiple
Exchange organizations, such as:
Free/Busy lookups
Calendar sharing
Message Tracking
MailTips
Multi-mailbox search
Federated Delegation requires a Federation Trust to be created
with the Microsoft Federation Gateway (MFG) in order to function
Communication between Exchange organizations and the
Microsoft Federation Gateway occurs securely over HTTPS
16

Microsoft
Federation
Gateway

The MFG is a free cloud-based identity service offered by

Microsoft
The MFG acts as the trust broker between federated Microsoft
Exchange Server 2010/2013 organizations
It is responsible for issuing delegation tokens to Exchange
recipients when they request information, such as free/busy,
from recipients in other federated Exchange organizations
These delegation tokens allow users from one federated
organization to be trusted by another federated organization

17

Federation
Trust

To use Exchange federated delegation features you must establish a federation

trust between your Exchange 2010/2013 server and the MFG
A self-signed certificate is automatically created when establishing a trust
and is used for signing and encrypting delegation tokens
Establishing a federation trust exchanges the certificate details and
federation metadata with the MFG
When you create a federation trust an Application Identifier (App ID) is
automatically generated for your Exchange organization
This App ID is used by the MFG to uniquely identify your Exchange
organization
A federated Organization Identifier (Org ID) defines which of the authoritative
accepted domains configured in your organization are enabled for federation
Only recipients that have e-mail addresses with accepted domains
configured in the Org ID are recognized by the MFG and are able to use the
federated delegation features
This Org ID is comprised of a pre-defined string and any accepted domains
selected for federation e.g. FYDIBOHF25SPDLT.contoso.com and
contoso.com

18

Federation
Trust
Example

20

Organizatio
n
Relationshi
ps

Organization relationships are one-to-one relationships between

two Exchange organizations
Rather than requiring a complex Active Directory trust
configuration between the two organizations, both
organizations are just required to establish a one time
federation trust with the MFG

When you create an organization relationship with an external

organization, users in the external organization can access your
users' free/busy information, MailTips, and other Exchange
features
No replication of GAL information is required
Outlook 2010+ and OWA users can simply enter the SMTP
address of an external recipient when scheduling meetings in
order to see the Free/Busy information
21

Organizatio
n
Relationshi
ps
(continued)

When creating an organization relationship, you can specify one

of the following three levels of calendar availability access:
No free/busy access
Free/busy access with time only
Free/busy access with time, plus subject and location
Organization relationships work through the Client Access Server
connecting to the AutoDiscover Web service published by the
external organization to obtain the Availability service endpoint
which is then used to retrieve the relevant information using
Exchange Web Services

22

Hybrid
Server

With the configuration of a Hybrid deployment the onpremises Exchange 2010/2013 server designated for this
purpose is now referred to as a hybrid server
Hybrid servers are a requirement for hybrid deployments:
The server needs to be Exchange 2010 SP3 or Exchange
2013
The hybrid server enables messaging features and
message delivery between your on-premises and
Exchange Online organizations
Communicates with the Exchange Online servers using
exchange web services over HTTPS and SMTP over TLS

23

Hybrid
Server
License

The Hybrid server license key is provided at no cost

The key needs to be obtained from the Exchange Hybrid

Product Key Distribution website at http://aka.ms/hybridkey

Multiple servers can be licensed for redundancy

A valid Exchange Online subscription is required in order to

obtain the key

The server cannot be used for any other purposes other than
bridging the on-premises Exchange environment with Exchange
Online

24

Coexistenc
e Domain

The coexistence domain is a domain created for each Office 365

tenant in the format of <your tenant>.mail.onmicrosoft.com
domain
For example, a coexistence domain for Contoso would be
contoso.mail.onmicrosoft.com
The coexistence domain gets created when you activate DirSync
in your Office 365 tenant
AutoDiscover and MX record are created automatically for this
domain
Provides the backbone of all coexistence features
Will be added as an on-premises email address policy when the
HCW is run*
Mailboxes moved to Exchange Online will have the coexistence
domain stamped on their user object as a target address

25

Hybrid
Configurati
on Process

The Hybrid Configuration Wizard (HCW) reduces and

streamlines the overhead required to deploy a hybrid setup
The HCW automates and simplifies the configuration of the
following key elements:

Exchange federation trust

Organization

relationships

Remote domains
Accepted domains
Email address policies
Send/Receive connectors

EOP inbound/outbound
connectors
MRSProxy
Prerequisite checks

26

Use the Exchange

Remote Connectivity
Analyzer
to verify this stage

Before
Running the
HCW
Sign up
for Office
365

Register
your
domains
with
Office
365

ID Fix
and
Deploy
Office
365
Directory
Sync

General Office 365

deployment tasks

Install
Exchang
e 2013
CAS &
MBX
Servers

Publish
the CAS
Server
(Assign
SSL
certificat
e,
firewall
rules)

Exchange specific
deployment tasks

27

Run the
Hybrid
Wizard

The Hybrid
Configurati
on Engine

Provides a single configuration tool to enable and configure

hybrid deployments
Tool has built-in configuration logic to make necessary changes to
a new or existing hybrid configuration
Processes the Update-HybridConfiguration cmdlet actions
Engine compares the state of the Hybrid Configuration Active
Directory object with current configurations
It then executes tasks to match the deployment configuration
settings to the parameters defined in the Hybrid Configuration
Active Directory object
The following slide defines the steps the Engine performs

28

Running the
HCW

The following general steps are performed when the HCW is run:
Verifies prerequisites and performs topology checks:
Checks both on-premises and EXO organizations Exchange versions
Checks DirSync presence as well as Federated and accepted domains
Checks existing federation trust, organization relationships and
Exchange certificates
Testing Account credentials:
HCW ensures the accounts have the appropriate permissions and are
members of the Organization Management role group both onpremises and Office 365
Creates the Hybrid Configuration object:
Hybrid configuration data is stored in AD under the configuration
container and is created when the New-HybridConfiguration cmdlet is
called by the HCW
This object contains the configuration settings chosen during the HCW
29

Hybrid
Configurati
on Object

30

New
New organization
organization
level
level tab
tab that
that
contains
the
contains the
Hybrid
Hybrid
Configuration
Configuration
Object
Object

Exchange
2010
Hybrid
Configurati
on Wizard

End
End to
to end
end wizard
wizard
that
that guides
guides you
you
through
each
through each step
step
of
of configuring
configuring
hybrid
hybrid
31

New
New Hybrid
Hybrid section
section
within
within the
the Exchange
Exchange
Admin
Admin Center
Center that
that
contains
the
Hybrid
contains the Hybrid
Configuration
Configuration Object
Object

Exchange
2013
Hybrid
Configurati
on Wizard

End
End to
to end
end wizard
wizard that
that
guides
you
through
guides you through
each
each step
step of
of configuring
configuring
hybrid
hybrid
32

Hybrid
Deployment
Improvemen
ts in
Exchange
Server 2013

Adaptive HCW

Presents only questions needed to configure your hybrid

deployment

Integrated support for Exchange 2010 Edge Transport

Servers

Now configures Edge server for you

Enhanced Secure Mail

Static IP addresses for connector selection no longer required

Improved Centralized Mail Transport

Now supports the MX either pointing on-premise or Exchange

Online

Better Exchange Online Protection Support

More flexibility with inbound internet flow and MX changes

Unified Mailbox Move Wizard

Drive mailbox moves (in any direction) from the one location
using EAC
33

Troubleshooti
ng Hybrid
Configuration

The Update-HybridConfiguration cmdlet produces a log with each

execution

Located under:
<Exchange Install Directory>\Logging\Update-HybridConfiguration
The log will contain a record of each cmdlet run, the start and end time,
and also any errors that may have been thrown in the process
The Update-HybridConfiguration cmdlet calls many other cmdlets

When troubleshooting, it is critical to identify at what stage and with

what cmdlet the process has failed. Only then will the root be
identifiable
Here is a log sample:
[10/10/2011 2:11:49] INFO:Running command: Get-FederatedOrganizationIdentifier
-IncludeExtendedDomainInfo ''
[10/10/2011 2:11:49] INFO:Cmdlet: Get-FederatedOrganizationIdentifier --Start Time: 10/9/2011
10:11:49 PM.
[10/10/2011 2:11:49] INFO:Cmdlet: Get-FederatedOrganizationIdentifier --End Time: 10/9/2011
10:11:49 PM.
[10/10/2011 2:11:49] INFO:Cmdlet: Get-FederatedOrganizationIdentifier --Processing Time:
171.8816.
[10/10/2011 2:11:49] INFO:Needs Configuration state
[10/10/2011 2:11:49] INFO:Running command: Get-AvailabilityAddressSpace
[10/10/2011 2:11:49] INFO:Cmdlet: Get-AvailabilityAddressSpace --Start Time: 10/9/2011
10:11:49 PM.
[10/10/2011 2:11:49] INFO:Cmdlet: Get-AvailabilityAddressSpace --End35
Time: 10/9/2011 10:11:49
PM.

Exchange 2013 Hybrid Deployment from an Existing Exchange 2007 or 2010

Environment
1. Prepare

Clients

Office 365

autodiscover.contoso.c
om
mail.contoso.com
Autodiscover &
EWS SMT
P

E2010 or E2010 or
2007 Hub 2007 CAS

E201
3 CAS

SP/RU

Exchange
2010 or 2007
Servers
SP/RU

Intranet site

6
E2010
or
2007
MBX

E2013
MBX

Internet facing site

Install required Exchange service packs or update

rollups to existing servers and prepare AD for
Exchange 2013 schema
2. Deploy Exchange 2013 servers
Install both Exchange 2013 MBX and CAS
server roles
Set an ExternalUrl for the Exchange Web
Services virtual directory
3. Obtain and Deploy Certificates
Obtain and deploy certificates on the
Exchange 2013 CAS and Mailbox servers
4. Publish protocols externally
Create public DNS A records for the EWS and
SMTP endpoints. Validate using Remote
Connectivity Analyzer
5. Switch AutoDiscover to the Exchange
2013 CAS
Change the public AutoDiscover DNS record to
to Hybrid
the Exchange
2013 CASWizard
6. resolve
Run the
Configuration
7. Move mailboxes
36

Example
Hybrid
Topology

37

Hybrid Deployment Free/Busy Lookup Process

On-premises user
SMTP:paul@contoso.c
om

Exchange Online User

SMTP: crystal@contoso.com
smtp:crystal@contoso.mail.onmicrosof
t.com

Microsoft Federation
Gateway

1. Request free/busy for

crystal@contoso.com
10. Display free/busy for
Crystal

5. Generate token

7. Obtain free/busy
information

2. Read TargetAddress from Crystals Remote

Mailbox object crystal@contoso.mail.onmicrosoft.com

3. Verify Org Relationship exists

for contoso.mail.onmicrosoft.com

Hybrid Server
/ews
On-Prem to O365 Org Relationship
Domain: contoso.mail.onmicrosoft.com.com
Endpoint: https://outlook.com/EWS

Contoso

8. Verify Org relationship exists for

contoso.com

4. Submit request for delegation

token

Ex2013 CAS
6. Authenticate with token and
submit free/busy request
9. Return free/busy

/ews

O365 to On-Prem Org Relationship

Domain: contoso.com
Endpoint: https://mail.contoso.com/EWS
38

Consideratio
ns for
Exchange
Server 2003
Mailboxes

In order to process Free/Busy requests for Exchange 2003 mailboxes the

Mailbox Role must be installed on the Hybrid server so that a Public Folder
Store exists

A new free/busy folder called External (FYDIBOHF25SPDLT) will be created

when the Hybrid wizard is run

Free/Busy lookups for Exchange 2003 mailboxes work like this:

The RPC Client Access Service running on the Hybrid server intercepts any
Free/Busy request destined for this folder and routes it to the Availability Service
The Availability Service detects it is a request for Office 365
The request is passed to the destination Client Access Server in Exchange Online
The response is placed back as a message in the External
(FYDIBOHF25SPDLT) public folder for Outlook to consume and is cached for 15
minutes

The External (FYDIBOHF25SPDLT) public folder must not be replicated to

any non Exchange server not running a minimum of Exchange 2010 SP1

39

Troubleshootin
g Organization
Relationships

Use the Test-OrganizationRelationship cmdlet which performs the

following:

Verifies that there is an organization relationship in place onpremises and that Exchange can successfully perform external
lookups
Verifies that the organization relationship has a configured
TargetAutodiscoverEPR value, and verifies that Exchange can
resolve the AutoDiscover settings
Retrieves Federation information from the MFG including certificate
status information
If the -UserIdentity parameter is specified, verifies that the
organization relationship is in place for the users SMTP addresses
and that Exchange can request delegation tokens for those users
Tests delegation tokens

40

Trusted and
Secure Mail
Flow

All messages that are sent between recipients in your on-premises

organization and Exchange Online are sent over a secure connection using
TLS
The Hybrid wizard creates a dedicated send connector on-premises
scoped to the coexistence domain (contoso.mail.microsoftonline.com)
An outbound connector in EOP is also created and is scoped to the default
SMTP domain (contoso.com)
Each organization is configured to treat messages sent from the other
organization as internal
This allows messages to bypass anti-spam settings and other services
The TLS connection between on-premises and ExO requires that the onpremises server accepting the connection must be a minimum of Exchange
2010 SP1
This can be an Exchange 2010 SP1 Edge Server
Any other SMTP end point accepting the messages will cause the required
headers to be lost which will impact secure mail functionality
41

Secure Mail

Third Party
Email
Security
System

Internet

External Recipient

MX resolves
MX is
Outbound
toYou
on-canto
switched
Exchange
premises
Exchange
choose to
Online
traffic
gateway
Online
route
isProtection
delivered
outbound
direct
on-premises
mail via EOP

Exchange Online
Protection

Secure Mail
Encrypted & Authenticated Mail Flow
David
Exchange
On-premises
Mailbox
On-Premises
Organization

Chris
Cloud
Mailbox

42

Exchange Online

Hybrid
Transport
Options

In addition to choosing how inbound messages are routed, you can

also choose how outbound messages sent from Exchange Online
recipients are routed. The following describes the available options:

Centralized mail control: This option routes outbound

messages sent from the Exchange Online users through onpremises
This enables you to apply compliance rules to these
messages that must be applied to all of your recipients,
regardless of whether they're located in Exchange Online or
on-premises

Decentralized mail control: This option routes outbound

messages sent from Exchange Online directly to the Internet
Use this option, if you do not need to apply any on-premises
policies or other processing to messages that are sent from
recipients in the Exchange Online
43

Centralized
Transport

Third Party
Email
Security
System

Internet

External Recipient

Secure Mail
Encrypted & Authenticated Mail Flow
David
Exchange
On-premises
Mailbox
On-Premises
Organization

MXAllresolves
email in
MX is
to
onand out
of the
switched
to
premises
Exchange
Exchange
gateway
Online
tenant
Online
must go via
Protection
on-premises

Exchange Online
Protection

Chris
Cloud
Mailbox

Exchange Online
44

Mailbox
Migrations

45

Component
s Used for
Mailbox
Moves

Mailbox Replication Service (MRS):

Uses remotes procedure calls to move mailboxes between onpremises servers
Mailbox Replication Service Proxy (MRSProxy):
Uses HTTPS Exchange Web Services calls to move mailboxes
between on-premises and Exchange Online or other Exchange
organizations
Mailbox moves occur between the on-premises Hybrid server
and the Exchange Online Client Access Servers
For large or distributed environments, multiple migration
endpoints (MRSProxy) servers are deployed to accelerate
concurrent migrations into a single tenant.

46

Mailbox
Migration

All mailbox migrations are driven from the Exchange Admin

Center through a unified mailbox move wizard
Moves are pulled from on-premises to the cloud. This means
that you schedule a migration from the cloud
All move types now support the new batch architecture. This
allows for easier creation and management of multiple
mailbox moves
As with Exchange 2010, hybrid (MRS based) mailbox moves
support off-boarding from the cloud to on-premises
During mailbox moves users can still access their mailboxes
as long as the source mailbox is Exchange Server 2007 SP2 or
higher

47

The Remote
Mailbox
Move
Process

A corresponding mail-enabled user needs to exist in Office

365 for the mailbox you plan to move. This would have been
created by DirSync
The new mailbox move request is queued in Exchange Online
and paced by the data center
Once the mailbox has been moved the on-premises mailbox is
soft deleted and the user is converted into a Remote User
Mailbox
The LegacyExchangeDN attribute is restamped to
/ou=External
The original LegacyExchangeDN is moved to an x500 proxy
address in order to preserve reply-ability to old emails
A TargetAddress gets set on the user object that points to
the coexistence domain

48

Outlook
And Mailbox
Migrations

Outlook detects the mailbox has been moved and prompts the
user to close and reopen Outlook
Outlook then performs an AutoDiscover lookup against the
email domain found in the TargetAddress attribute of the
user which will resolve to Exchange Online
Outlook updates the users Outlook profile automatically with
the new connection details
The mailbox move persists the msExchMailboxGUID which
means no .ost resynchronization needs to occur post mailbox
move

49

SoftDeleted
Mailboxes

Source mailboxes on-premises are not hard-deleted after the

mailbox move completes
They are soft-deleted so the mailbox data is accessible for
restore operations if required
To restore use the New-MailboxRestoreRequest cmdlet
Soft-deleted mailboxes are retained until the retention period
expires or you use the Remove-StoredMailbox cmdlet to purge
them
To view soft-deleted mailboxes use the Get-MailboxStatistics
cmdlet

50

OffBoarding
Mailboxes

You may want to off-board because of:

Long-term coexistence scenarios
Compliance requirements (retaining ex-employee data)
Piloting the online environment but not committed to the
move
Off-boarding:
Is done through the Exchange Online EAC
Moving a mailbox back to an on-premises Exchange Server
2010/2013 database is an online mailbox move
Moving a mailbox back to an on-premises Exchange Server
2003 or Exchange Server 2007 database is an offline mailbox
move
Without a hybrid deployment in place, off-boarding is
performed by exporting mailbox data to a .pst file by using
Outlook or a partner solution
51

Lab: Run the

HCW and
Configure a
Hybrid
Deployment

52

Module
Review

1. Why are organization relationships important?

2. What is the purpose of the coexistence domain used in a
hybrid deployment?
3. What is the purpose of MRSProxy?
4. How does the remote mailbox move process prevent ost
resynchronization by preserving the exist .ost file

53

Module
Summary

In

this Lesson, you learned:

Basic Terminology used in Hybrid Deployments
The differences between Exchange 2010 vs. Exchange 2013
Hybrid Deployment Configuration
How to Use the Hybrid Configuration Wizard
Hybrid Deployment Mail Flow and how it works
The move mailbox process

55

 2013
2012 Microsoft Corporation. All rights reserved. Microsoft, Windows, Windows Vista and other product names are or may be registered trademarks and/or trademarks
in the U.S. and/or other countries. The information herein is for informational purposes only and represents the current view of Microsoft Corporation as of the date of
this presentation. Because Microsoft must respond to changing market conditions, it should not be interpreted to be a commitment on the part of Microsoft, and
Microsoft cannot guarantee the accuracy of any information provided after the date of this presentation.MICROSOFT MAKES NO WARRANTIES, EXPRESS, IMPLIED OR
STATUTORY, AS TO THE INFORMATION IN THIS PRESENTATION