Module 18Exchange Online Hybrid Coexistence

Presenter namePresenter 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

4

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

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Overview of a Hybrid Deployment

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What is a Hybrid Deployment

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)

7

Hybrid Deployment Benefits

• Delegated authentication between on-premises and Exchange Online Web services

• Enables Free/Busy, calendar sharing, message tracking, online archive and more

Federation Trust

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

Integrated Admin

Experience• Online mailbox moves• Preservation of the Outlook profile and OST file• Leverages the Mailbox Replication Service

(MRS)

Native Mailbox Move

• Authenticated and encrypted mail flow• Preserves the internal Exchange message

headers• Support for compliance mail flow scenarios

(centralized transport)

Secure Mail Flow

8

Hybrid Coexistence Feature Comparison

9

Hybrid Deployment Prerequisites

• 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

10

Hybrid Deployment Exchange Requirements

• 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

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Hybrid Server Roles

12

Hybrid Deployment 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

13

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 on-

premises Enterprise pivot within EAC and allow DirSync to replicate the changes to Office 365

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Hybrid Deployment Implementation and Architecture

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Collaboration 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

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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

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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

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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

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Federation Trust Example

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Organization Relationships

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

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Organization Relationships (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

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Hybrid Server

• With the configuration of a Hybrid deployment the on-premises 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

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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

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Coexistence 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

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Hybrid Configuration 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

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Before Running the HCW

Exchange specific deployment tasks

General Office 365 deployment tasks

Sign up for Office 365

Register your

domains with Office

365

ID Fix and Deploy

Office 365 Directory

Sync

Install Exchange 2013 CAS

& MBX Servers

Publish the CAS Server(Assign SSL certificate,

firewall rules)

Run the Hybrid Wizard

Use the Exchange Remote Connectivity Analyzer

to verify this stage

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The Hybrid Configuration 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

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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 on-premises 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

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Hybrid Configuration Object

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Exchange 2010 Hybrid Configuration Wizard

End to end wizard that guides you

through each step of configuring

hybrid

New organization level tab that contains the

“Hybrid Configuration

Object”

32

Exchange 2013 Hybrid Configuration Wizard

New Hybrid section within the Exchange Admin Center that

contains the “Hybrid Configuration Object”

End to end wizard that guides you through

each step of configuring hybrid

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Hybrid Deployment Improvements 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

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Troubleshooting 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 identifiableHere 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 --End Time: 10/9/2011 10:11:49 PM.[10/10/2011 2:11:49] INFO:Cmdlet: Get-AvailabilityAddressSpace --Processing Time: 15.6256.[10/10/2011 2:11:49] INFO:Configuration state[10/10/2011 2:11:49] INFO:Running command: Get-WebServicesVirtualDirectory -Server 'E14SP2-E2K10'

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2. Deploy Exchange 2013 serversInstall both Exchange 2013 MBX and CAS server rolesSet an ExternalUrl for the Exchange Web Services virtual directory

E2010 or 2007 Hub

Internet facing site

Intranet site

Exchange 2010 or 2007

Servers

1. PrepareInstall required Exchange service packs or update rollups to existing servers and prepare AD for Exchange 2013 schema

4. Publish protocols externallyCreate public DNS A records for the EWS and SMTP endpoints. Validate using Remote Connectivity Analyzer5. Switch AutoDiscover to the Exchange

2013 CASChange the public AutoDiscover DNS record to resolve to the Exchange 2013 CAS6. Run the Hybrid Configuration Wizard

E2013 CAS

3. Obtain and Deploy CertificatesObtain and deploy certificates on the Exchange 2013 CAS and Mailbox servers

Clientsautodiscover.contoso.commail.contoso.com

1 2

3

45

6

E2010 or 2007 CAS

E2010 or

2007 MBX

E2013 MBX

SP/RUSP/RU

Office 365

7. Move mailboxes

Autodiscover & EWS SMT

P

7

Exchange 2013 Hybrid Deployment from an Existing Exchange 2007 or 2010 Environment

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Example Hybrid Topology

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Microsoft Federation Gateway

On-premises userSMTP:paul@contoso.com

Contoso

On-Prem to O365 Org RelationshipDomain: contoso.mail.onmicrosoft.com.comEndpoint: https://outlook.com/EWS

O365 to On-Prem Org RelationshipDomain: contoso.comEndpoint: https://mail.contoso.com/EWS

3. Verify Org Relationship exists for contoso.mail.onmicrosoft.com

1. Request free/busy for crystal@contoso.com

9. Return free/busy/ews /ews

4. Submit request for delegation token

8. Verify Org relationship exists for contoso.com

Hybrid Server Ex2013 CAS

Exchange Online UserSMTP: crystal@contoso.comsmtp:crystal@contoso.mail.onmicrosoft.com

2. Read TargetAddress from Crystal’s Remote Mailbox object - crystal@contoso.mail.onmicrosoft.com

5. Generate token

6. Authenticate with token and submit free/busy request

10. Display free/busy for Crystal 7. Obtain free/busy

information

Hybrid Deployment Free/Busy Lookup Process

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Considerations 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

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Troubleshooting Organization Relationships

Use the Test-OrganizationRelationship cmdlet which performs the following:• Verifies that there is an organization relationship in place on-

premises 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

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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 on-premises 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

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Secure Mail

On-Premises Organization

External Recipient

Exchange

Exchange Online

Exchange Online Protection

Inte

rnet

Third Party Email

Security System

“Chris”Cloud

Mailbox

“David”On-premises

Mailbox

Secure MailEncrypted & Authenticated Mail Flow

MX resolves to on-

premises gateway

MX is switched to Exchange

Online Protection

Outbound Exchange

Online traffic is delivered

direct

You can choose to

route outbound

on-premises mail via EOP

43

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 on-premises• 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

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Centralized Transport

Exchange Online

Exchange Online Protection

On-Premises Organization

Exchange

Third Party Email

Security System

External Recipient

Inte

rnet

“Chris”Cloud

Mailbox

“David”On-premises

Mailbox

Secure MailEncrypted & Authenticated Mail Flow

MX resolves to on-

premises gateway

All email in and out of the

Exchange Online tenant must go via on-premises

MX is switched to Exchange

Online Protection

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Mailbox Migrations

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Components Used for Mailbox Moves

Mailbox Replication Service (MRS):• Uses remotes procedure calls to move mailboxes between

on-premises 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.

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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

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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

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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 user’s 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

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Soft-Deleted 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

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Off-Boarding 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

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Lab: Run the HCW and Configure a Hybrid Deployment

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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

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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

© 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

© 2013 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