Mod 7: Exchange Online

Deployment & Migration

Version 2.0 for Office 365

Chris Oakman | Managing Partner Infrastructure Team | Eastridge Technology

Stephen Hall | CEO & SMB Technologist | District Computers
Jump Start Schedule – Target Agenda
Day 1 Day 2
Administering Office 365 Administering Exchange Online
Office 365 Overview & Infrastructure Lync Online Administration

Office 365 User Management Administering SharePoint Online

Office 365 DirSync, Single Sign-On & ADFS Exchange Online Basic Management

MEAL BREAK

Exchange Online Deployment & Migration

Exchange Security & Protection

Exchange Online Archiving & Compliance

Module 7: Exchange Online Deployment &
Migration
For Midsize Businesses and Enterprises

• Deployment Considerations
• Migration Options Decision Framework
• Simple Migrations
• Exchange Cutover Migration
• Staged Migration
• Remote Move Migration
Migration Options
• Remote Move Migration
 Used to migrate on-premises Exchange mailboxes to Exchange Online in an
Exchange hybrid deployment
 Requires a hybrid deployment
• Staged Exchange Migration
 mailboxes in your on-premises Exchange organization are migrated to Exchange
Online in batches. A staged Exchange migration is a good option if your current
on-premises email organization and migration goals meet the following conditions
Migration Options
• Cutover Exchange Migration
 mailboxes in your on-premises Exchange organization are migrated to Exchange
Online in a single migration batch
• IMAP Migration
 contents of users' mailboxes on an IMAP messaging system are migrated to their
Exchange Online mailboxes
Compare Migration Types
Do you want to manage user
Existing organization Number of mailboxes to migrate accounts in your on-premises Migration type
organization?

Exchange 2013, Exchange 2010, Less than 1,000 mailboxes No Cutover Exchange migration
Exchange 2007, or Exchange 2003

Exchange 2007 or Exchange 2003 Less than 1,000 mailboxes No Staged Exchange migration

Exchange 2007 or Exchange 2003 More than 1,000 mailboxes Yes Staged Exchange migration or
remote move migration in an
Exchange hybrid deployment

Exchange 2013 or Exchange 2010 More than 1,000 mailboxes Yes Remote move migration in an
Exchange hybrid deployment

Exchange 2000 Server or earlier No maximum Yes IMAP migration

versions

Non-Exchange on-premises No maximum Yes IMAP migration

messaging system
Included Web-based Exchange Migration

• Free migration tools

• No software to install
• Migrate email, calendar,
contacts, and tasks from
Exchange 2003, 2007,
2010
• Migrate email from all
platforms that support
IMAP
• Allows fast cutovers
or staged migration

Additional options available with

tools from migration partners
Module 7: Exchange Online Deployment &
Migration
For Midsize Businesses and Enterprises

• Deployment Considerations
• Migration Options Decision Framework
• Simple Migrations
• Exchange Cutover Migration
• Staged Migration
• Remote Move Migration
Exchange Server 2013 Deployment Assistant
A good way to determine which migration type to use to migrate mailboxes to Exchange Online is by using the
Exchange Server 2013 Deployment Assistant. It's a web-based tool that helps you deploy Exchange 2013 in your
on-premises organization, configure an Exchange hybrid deployment between your on-premises and Office 365
organizations, or migrate on-premises mailboxes to Office 365. The Deployment Assistant asks you a small set of
questions and then, based on your answers, provides instructions to deploy and configure Exchange 2013 in an
on-premises hybrid deployment, or migrate mailboxes to Office 365.

Exchange 2013 Deployment Assistant 

Choice of Migration Solutions
Picking Exchange Migration Solution
Hybrid Co-existence

Stage Exchange Migration (SEM)

Migration Solutions

Cutover Exchange
Migration (CEM)

1 150 5,000 25,000

Organizational Size in Users
<1 Week 2 Weeks 3 Weeks Several Months

Time For Migration including Planning

None Mailflow/GalSync Free/Busy, Archive in Cloud

Coexistence Requirements
Deployment Plan Decision Factors
Cutover vs. Hybrid
“Can I do this it weekend?”
Cutover Hybrid
• Executed over a weekend; switch the • Executed over period of
MX record time (week, month, year)
• All users moved as part of a “big • No requirement to flip “a
switch” to the cloud switch”
 Pilot mailboxes with alternate domain name • Can run in hybrid scenario
(i.e., DOMAIN.onmicrosoft.com) indefinitely
• No on-premises configuration or • Requires on-premises
hardware requirement configuration and
hardware
Module 7: Exchange Online Deployment &
Migration
For Midsize Businesses and Enterprises

• Deployment Considerations
• Migration Options Decision Framework
• Simple Migrations
• Exchange Cutover Migration
• Staged Migration
• Remote Move Migration
IMAP/POP Cutover Migration

Migrate E-Mail from an IMAP Server to Cloud-based Mailboxes

http://technet.microsoft.com/en-us/library/jj159545.aspx
IMAP/POP Migration Requirements
• On-premises migration tool is not required
• Access to IMAP ports (TCP/143/993)
• Users must be provisioned in the cloud prior to migration
 Bulk provisioning, CSV parser, manual, etc.
• Gather user credentials or setup admin credentials
• Prepare a CSV file with list of users
 EmailAddress, UserName, Password
 Max of 50,000 rows
 Max 10 MB in size
Scope: Migrated vs. Not-Migrated
• What is migrated:
 Mail messages (Inbox and other folders)
 Maximum of 500,000 items
 Possible to exclude specific folders from migration
(e.g. Deleted Items, Junk E-Mail)
• What is not migrated:
 Contacts, Calendars, Tasks, etc.
 Excluded folders
 Folders with a forward slash ( / ) in the folder name
 Messages larger than 35 MB
End User Experience
• Admin must distribute new passwords
 Users’ Outlook profiles must be re-created using new password
• All mail is downloaded from the Office 365 mailbox
 i.e. the OST file must be recreated
• User sets personalized password
• User recreates Calendar, Contacts, Tasks, Signatures and
Autocompletes 
Typical IMAP/POP Cutover Migration
Flow
Provision users …
in
Office 365

Initial sync

Gather
credentials and Incremental syncs
prepare CSV

Change MX record
Enter server
settings and
upload CSV Complete Migration

… Final Sync/Cleanup
Module 7: Exchange Online Deployment &
Migration
For Midsize Businesses and Enterprises

• Deployment Considerations
• Migration Options Decision Framework
• Simple Migrations
• Exchange Cutover Migration
• Staged Migration
• Remote Move Migration
Exchange Cutover Migration

Migrate All Mailboxes to the Cloud with a Cutover Exchange Migration

http://technet.microsoft.com/en-us/library/jj874016(v=exchg.150).aspx
Exchange Cutover Migration
• Objective • Capability
 A simple Exchange migration • Migration without the need
solution for small and medium for on-premise tools
businesses to move to Office 365 • Migration from Exchange
Server 2003 and greater
• On-premise or hosted
• Requirement systems
 Organization should be less than • Integrated provisioning
1000 in size • High fidelity migrations - mail,
 Outlook Anywhere service
calendar, tasks and many
 Identity management in the cloud more
Requirements For Cutover Migrations
• Outlook Anywhere on source Exchange Org
 Must have SSL certificate issued by a public CA
• Migration Account with Full Access or Receive-As permissions to all
mailboxes that will be migrated
• SMTP domain(s) configured in Office 365 tenant
• DirSync cannot be enabled on the Office 365 tenant
• Max of 1,000 mailboxes
Accounts and Passwords Provisioning
• Accounts Provisioning
 Migration process creates users, mailboxes, distribution groups and e-mail contacts
 Mailboxes are configured so that replies to migrated messages will work after
migration
(i.e. provision process brings over the Legacy DNs)
• Passwords
 No access to passwords from source directory
 New passwords created for all provisioned users
 A link to download passwords is sent to admin
 Users must change password on their first login
Migration Flow
Limitations of Cutover Migrations
• These items are NOT migrated
 Security Groups, Dynamic Distribution Lists, System mailboxes, Dumpster, Send-As
Permissions, messages larger than 35 MB
 Mailboxes enabled for Unified Messaging cannot be migrated
 Existing cached-mode files (OST files) cannot be preserved
• Partial migrations are not possible
 Folder exclusion
 Time range selection
• Not possible to configure the incremental sync interval (24 hours)
What’s Migrated
• Message Items • Calendar items • Other Items
• Delivery Reports • Recurrences • Tasks
• Read/Non-Read Receipts • Exceptions • Notes
• NDRs • Meeting • Contacts
• Folders Requests/Cancelations • Public delegates
• Rules /Responses • Folder permissions
• Categories • Out-of-Office settings • Custom forms
• Categories • Outlook settings (e.g.
folder favorites)
End User Experience
• Admin needs to distribute new passwords to end users
• Users’ Outlook profiles are re-created using new password
• All mail is downloaded from the Office 365 mailbox
 (i.e. the OST file must be re-created)
• User sets personalized password
Typical Exchange Cutover Migration Flow
Module 7: Exchange Online Deployment &
Migration
For Midsize Businesses and Enterprises

• Deployment Considerations
• Migration Options Decision Framework
• Simple Migrations
• Exchange Cutover Migration
• Staged Migration
• Remote Move Migration
Staged Exchange Migration

Migrate All Mailboxes to the Cloud with a Staged Exchange Migration

http://technet.microsoft.com/en-us/library/jj898486(v=exchg.150).aspx
Exchange Staged Migration
• Objective  Capability
 Simple Exchange migration  Migration from Exchange
solution for medium and Server 2003 and Exchange
large size organizations 2007 only (*)
 Migrate in batches
 High fidelity migrations
 Mail, calendar, tasks & many
more
 * for Exchange 2010 or
2013 consider Cutover
or Hybrid
Requirements For Staged Migrations
• Outlook Anywhere on source Exchange Org
 Must have SSL certificate issued by a public CA
• Migration Account with Full Access or Receive-As permissions to all
mailboxes that will be migrated
• SMTP domain(s) configured in Office 365 tenant
• DirSync must be enabled on the Office 365 tenant
• Simple Coexistence
• No limit on the overall number of mailboxes to migrate (up to
1,000 mailboxes in each CSV batch)
Simple Coexistence
• Use DirSync to establish address book in Office 365
• Mail flow between all mailboxes
• During migration, mailboxes exist across on-premises and Office
365
• End goal is to fully migrate to Office 365
• No Free/Busy calendar sharing
Accounts and Passwords Provisioning
• Accounts Provisioning
 For every on-premises mailbox to be migrated there needs to be a MEU or
Mailbox in Office 365
 Migration Service relies on DirSync to do the provisioning
• Passwords
 Target mailbox passwords need to specified for all the users
 Administrators can force users to change passwords on first login
• Profiles
 Users must create new Outlook Profiles
• Staged batches of 1,000 users (max per batch), no upper limit
 Incremental syncs not needed
• Users start using their cloud mailboxes upon creation
 New mail is available immediately, old content fills in
• Stamps targetAddress on source mailboxes to support mail flow
from on-premises to cloud (*)
• Optional password change

*In Exchange 2010 and Exchange 2013, the TargetAddress property can't be modified.

This is the reason that staged Exchange migration doesn't support migrating Exchange
2010 and Exchange 2013 mailboxes to Exchange Online.
Typical Exchange Staged Migration Flow
Module 7: Exchange Online Deployment &
Migration
For Midsize Businesses and Enterprises

• Deployment Considerations
• Migration Options Decision Framework
• Simple Migrations
• Exchange Cutover Migration
• Staged Migration
• Remote Move Migration
Remote Move Migration

Exchange Server 2013 Hybrid Deployments

http://technet.microsoft.com/en-us/library/jj200581(v=exchg.150).aspx
Remote Move Migration
• Objective  Capability
 provides the seamless look and  Migration from Exchange Server
feel of a single Exchange 2010 and Exchange 2013 only
organization between an on-  Migrate in batches, groups or one
premises Exchange Server at a time
2013 organization and  Free/busy and calendar sharing
Exchange Online in Microsoft between on-premises and
Office 365 Exchange Online
 Mail, calendar, tasks & many more

**You have to implement a hybrid deployment to migrate more than 1,000 Exchange 2010 or
Exchange 2013 mailboxes to Exchange Online.
Hybrid Key Features
• Delegated authentication for on-premises/cloud web services
Federation Trust • Enables Free/Busy, calendar sharing, message tracking, online
archive, and more

Integrated Admin • Manage all of your Exchange functions, whether cloud or on-
premises from the same place - Exchange Administration Center
Experience (EAC)

Native Mailbox • Online mailbox moves

• Preserve the Outlook profile and offline file (OST)
Move • Leverages the Mailbox Replication Service (MRS)

• Authenticated and encrypted mail flow

Secure Mail Flow • Preserves the internal Exchange messages headers
• Support for compliance mail flow scenarios (central transport)
Hybrid Coexistence Feature Comparison
Feature Simple Hybrid
Mail routing between on-premises and cloud (recipients on either side)  
Mail routing with shared namespace (if desired) on both sides  
Unified GAL  
Free/Busy and calendar sharing cross-premises 
Out of Office understands that cross-premises is “internal” to the organization 
Mailtips, messaging tracking, and mailbox search work cross-premises 
OWA redirection cross-premise (single OWA URL for both on-premises and cloud) 
Single tool to manage cross-premises Exchange functions (including migrations) 
Mailbox moves support both onboarding and offboarding 
No outlook reconfiguration or OST resync required after mailbox migration 
Preserve auth header (ensure internal email is not spam, resolve against GAL, etc.) 
Centralized mail flow , ensures that all email routes inbound/outbound via on-prem 
Requirements for Remote Move Migration
• Exchange 2013 CAS/MBX server on-premises
• Hybrid configuration in place
 On-premises config, O365 config, federation using MFG, certificates, etc.
 Much of the config is automated by the Hybrid Configuration Wizard
• SMTP domain(s) configured in O365 tenant
• Directory Sync tool enabled in O365 tenant
2013 Hybrid Limitations
• Exchange 2003 is not supported
• Delegation coexistence cross-premises
(delegate permissions are migrated when users are in
the same batch)
• Migration of Send As/Full Access permissions
Hybrid user experience
• If configured for SSO, users login with their AD credentials.
Otherwise, admin needs to distribute new password to
user.
• User’s current Outlook profile is updated with the Exchange
Online server name via Autodiscover.
• Offline files (OST files) do not have to be recreated.
• If using Outlook at the time of the mailbox move, user is
prompted to close and reopen Outlook.
Remote Move Migration Process

Publish the
Register Install
Deploy CAS Server
your Exchange Run the
Sign up for Office 365 2013 CAS & (Assign SSL
domains Hybrid
Office 365 Directory MBX Servers certificate,
with Office Wizard
Sync firewall
365 (Edge opt)
rules)

General Office 365 deployment tasks Exchange specific deployment tasks

(deep dive on next slide)
• Migration Tools Set of Hybrid Move Cmdlets
• Also available via  New-MoveRequest

PowerShell  Get-MoveRequest
 Get-MoveRequestStatistics
 Suspend-MoveRequest
• Example:-  Resume-MoveRequest
• new-MoveRequest -identity $_.UserPrincipalName -Remote
-RemoteHostName 'mail.company.com' -RemoteCredential
$cred -TargetDeliveryDomain
 Remove-MoveRequest
‘tenantname.mail.onicrosoft.com'
Resources
• Exchange Deployment Assistant
 http://technet.microsoft.com/en-US/exdeploy2013/Checklist?state=1119-W-AAAAAAAAQAAAAA~~

• IMAP/POP Migration
 http://technet.microsoft.com/en-us/library/jj159545.aspx

• Exchange Cutover Migration

 http://technet.microsoft.com/en-us/library/jj874016(v=exchg.150).aspx ‘

• Exchange Staged Migration

 http://technet.microsoft.com/en-us/library/jj898486(v=exchg.150).aspx

• Exchange Remote Move Migration

 http://technet.microsoft.com/en-us/library/jj200581(v=exchg.150).aspx