Moving your business to Office 365 may seem like a pretty daunting task but with a careful planning you could be up and running before you know it. In this deep dive we take you through the maze of planning to configuration and mail migration. Exploring simple, staged and hybrid solutions. Packed with tips, tricks and solutions that will ensure your adoption of Office 365 will be a smooth one. We will cover various scenarios, from a simple hosted email migration to the complexities of the Exchange hybrid.

1. OFC312

3. Introduction
Are you ready to make the move
Identity
Email migrations
IMAP migrations
Exchange cutover and staged migrations
Exchange Hybrid

5. Microsoft Cloud Principles

6. Service Descriptions and Updates
http://technet.microsoft.com/en-us/library/jj819284.aspx
http://office.microsoft.com/en-nz/products/office-365-roadmap-FX104343353.aspx
http://technet.microsoft.com/en-us/library/office-365-system-requirements.aspx
http://blogs.office.com
http://deploy.office.com/

9. Network Requirements
http://technet.microsoft.com/en-us/library/jj688118.aspx
http://www.microsoft.com/en-
us/download/details.aspx?id=19011
http://gallery.technet.microsoft.com/office/Exchange-Client-Network-8af1bf00
http://technet.microsoft.com/en-
us/library/cc262952(v=office.12).aspx
http://onlinehelp.microsoft.com/en-us/office365-enterprises/hh416761.aspx

11. Connecting to Office 365
http://onlinehelp.microsoft.com/en-us/office365-enterprises/hh373144.aspx
http://technet.microsoft.com/en-us/exchangelabshelp/gg263350
http://go.microsoft.com/fwlink/?linkid=236301
http://office.microsoft.com/en-au/business/office-365-trust-center-cloud-
computing-security-FX103030390.aspx

13. Office 365
http://www.microsoftvirtualacademy.com/
http://office.microsoft.com/en-au/support/office-365-administrator-resource-
center-FX103995410.aspx
https://www.microsoft.com/learning/en-au/office365-training.aspx
http://ignite.office.com
http://summit.office.com

14. Introduction
Are you ready to make the move
Identity
Email migrations
IMAP migrations
Exchange cutover and staged migrations
Exchange Hybrid

15. Federated IdentityCloud Identity
Directory & Password
Synchronization*
Single identity in the cloud
Suitable for small
organizations with no
integration to on-
premises directories
Single identity
Suitable for medium
and large organizations
without federation*
Single federated identity
and credentials
Suitable for medium and
large organizations

16. •
•
•
•

17. 1.
2.
3.
Technical requirements
4.
5.
6.
7.
Policy requirements
8.
9.
10.
11.
Existing infrastructure

18. Introduction
Are you ready to make the move
Identity
Email migrations
IMAP migrations
Exchange cutover and staged migrations
Exchange Hybrid

19. Migration
IMAP migration
Supports wide range of email platforms
Email only (no calendar, contacts, or tasks)
Cutover Exchange migration
Good for fast, cutover migrations
No Exchange upgrade required on-premises
Staged Exchange migration
No Exchange upgrade required on-premises
Identity federation with on-premises directory
Not just migration
Hybrid deployment
Manage users on-premises and online
Enables cross-premises calendaring,
smooth migration, and easy off-boarding
IMAP
migration
and 3rd
party tools
Cutover
migration
Staged
migration Hybrid
Exchange 5.5 X
Exchange 2000 X
Exchange 2003 X X X X*
Exchange 2007 X X X X
Exchange 2010 X X X
Exchange 2013 X X X
Notes/Domino X
GroupWise X
Other X

20. Control Deployment Type Description
User driven
New mailbox
User receives new “green field”
mailbox – i.e. user is onboarded to
without data migration.
New mailbox + Outlook PST
User receives new mailbox and either
attaches or imports PST files for
access to pre-Office 365 data.
New mailbox + connected accounts
User receives new mailbox and
configures connected accounts
via OWA.
Admin driven New mailbox + PST Import
User receives a new mailbox and
admin uses the PST Capture Tool to
import PST data into the user’s
Exchange Online mailbox.

21. 21 | Microsoft Confidential
DEPLOYMENT
PLAN
Migration
solution is part
of the plan
Source
server
Exchange
IMAP
Lotus Notes
Google
Size
Large
Medium
Small
Identity
management
On-premises
Single sign-on
On-cloud
Provisioning
DirSync
Manual/Bulk
Provisioning
Automatic
Provisioning
Coexistence
requirement
Simple
Rich
Migration option decision factors
21

22. Migration solutions
Cutover
Staged
Hybrid
small medium large
Organizational
size in users
<1 week 2 weeks 3 weeks several monthsTime for
migration
incl. planning
none mailflow/GALSync free/busy, archive in cloud
Features

23. In EAC, select
recipients | migration
Start migration
wizard
Choose migration
type and follow
prompts

24. Set of Migration Cmdlets
 New-MigrationBatch
 Start-MigrationBatch
 Get-MigrationBatch
 Get-MigrationStatus
 Complete-Migration
 Test-MigrationServerAvailability

26. Introduction
Are you ready to make the move
Identity
Email migrations
IMAP migrations
Exchange cutover and staged migrations
Exchange Hybrid

28. 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)
Not Migrated
 Contacts, Calendars, Tasks, etc.
 Excluded folders
 Folders with a forward slash
( / ) in the folder name
 Messages larger than 25 MB

29. Works with a large number of
source mail systems
Works with on-premises or
hosted systems
Users can be migrated in
batches
On-premises migration tool
is not required
Users + mailboxes must be
provisioned prior to migration

30. IMAP – Requirements and Limitations
 On-premises migration tool is not required
 Access to IMAP ports (TCP/143/993)
 Users + mailboxes must be provisioned prior to migration
 Bulk provisioning, CSV parser, manual, etc.
 SMTP domains configured in O365 tenant
 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

31. Migration CSV file

32. Delta
sync
every 24
hours
Mark
migration
as
complete
Change
MX
record
Gather
IMAP
creds and
prepare
CSV
IMAP – Migration Flow
Provision
users
+
mailboxes
in O365
(license
assigned)
Wizard:
Enter
server
settings
and
upload
CSV
Initial
sync
Final
sync and
cleanup

33. Introduction
Are you ready to make the move
Identity
Email migrations
IMAP migrations
Exchange cutover and staged migrations
Exchange Hybrid

35. Migrated
 Mail messages and folders
 Rules and categories
 Calendar (normal, recurring)
 Out-of-Office settings
 Contacts
 Tasks
 Delegates and folder perms
 Outlook settings (e.g. favorites)
Not Migrated
 Security Groups, DDLs
 System mailboxes
 Dumpster
 Send-As Permissions
 Messages larger than 25 MB

37. Existing Exchange environment
(Exchange 2003 or later)
Office 365
Users, contacts & groups via Outlook Anywhere (NSPI)
Mailbox data via Outlook Anywhere (MAPI)

38.  Accounts provisioning


 Passwords





40. Existing Exchange environment
(Exchange 2003 or 2007)
Office 365
Mailbox data via Outlook Anywhere (MAPI)
Users, contacts & groupsvia Outlook Anywhere (NSPI)
Office 365 Active
Directory synchronization

41.  Accounts provisioning
 Migration tool relies on DirSync to do provisioning
 For every on-premises mailbox to be migrated there needs
to be a MEU or Mailbox in Office 365
 Passwords
 Target mailbox passwords must be specified for all users
 Administrators can force users to change passwords
on first login

42. C/SEM Migration Scope
 Partial migrations are not possible (folder exclusion, time range)
 Mailboxes enabled for Unified Messaging cannot be migrated
 Existing cached-mode files (OST files) cannot be preserved
User Experience

43. Wizard:
Enter
server
settings
and admin
creds Delta
sync
every 24
hours
Mark
migration
as
complete
Change
MX
record
Initial
sync
Final
sync and
cleanup
License
users
Configure
Outlook
Anywhere
Test using
ExRCA
Assign
migration
perms
CEM
provisions
users
mailboxes
DLs
Contacts
SEM
configures
AD
attribute

44. Cutover
Cutover is designed for small/fast migrations to
Office 365
As the name sounds it’s an “all at once” move
Limited to a maximum of 1000 mailboxes total
Mailbox and address book data is synced from
on-premises to Exchange Online using Outlook
Anywhere (RPC over HTTPS)
Staged
Staged uses the same migration engine as
cutover but in conjunction with Office 365
directory synchronization to allow you to
move a few users at a time
Mailbox data is copied via Outlook Anywhere
Users/contacts and groups are synchronized
via Directory Sync
Exchange 2010 and later are not supported
(because hybrid-based is used instead)

45. Mail routing: pre-coexistence
On-premises
Messagefiltering
MX Record:
contoso.com
User Object
Mailbox-enabled
ProxyAddresses:
SMTP: John.Doe@contoso.com
ExchangeActive Directory

46. SEM Mail flow: on-premises to Office 365
On-premises
Messagefiltering
MX Record:
contoso.com
ExchangeActive Directory
Office 365
MX Record:
contoso.onmicrosoft.com
contoso.mail.onmicrosoft.com
ExchangeOnlineProtection
Exchange Online OnlineDirectory
DirSync DirSync Web
Service
Logon Enabled User
Mailbox-enabled
ProxyAddresses:
SMTP: John.Doe@contoso.com
smtp: John.Doe@contoso.onmicrosoft.com
smtp: John.Doe@contoso.mail.onmicrosoft.com
User Object
Mail-enabled (not mailbox-enabled)
ProxyAddresses:
SMTP: John.Doe@contoso.com
TargetAddresses:
SMTP: John.Doe@contoso.mail.onmicrosoft.com

47. SEM Mail flow: Office 365 to on-premises
On-premises
Messagefiltering
MX Record:
contoso.com
ExchangeActive Directory
Office 365
MX Record:
contoso.onmicrosoft.com
contoso.mail.onmicrosoft.com
ExchangeOnlineProtection
Exchange Online OnlineDirectory
DirSync DirSync Web
Service
Logon Enabled User
Mail-enabled (not mailbox-enabled)
ProxyAddresses:
SMTP: Jane.Doe@contoso.com
smtp: Jane.Doe@contoso.onmicrosoft.com
smtp: Jane.Doe@contoso.mail.onmicrosoft.com
TargetAddresses:
SMTP: Jane.Doe@contoso.com
User Object
Mailbox-enabled
ProxyAddresses:
SMTP: Jane.Doe@contoso.com

48. Introduction
Are you ready to make the move
Identity
Email migrations
IMAP migrations
Exchange cutover and staged migrations
Exchange Hybrid

50. Delegated authentication
for on-premises/cloud
web services
Enables free/busy,
calendar sharing,
message tracking &
online archive
Online mailbox moves
Preserve the Outlook
profile and offline folders
Leverages the Mailbox
Replication Service (MRS)
Manage all of your
Exchange functions,
whether cloud or on-
premises from the
same place: Exchange
Admin Center
Authenticated and encrypted mail
flow between on-premises and
the cloud
Preserves the internal Exchange
messages headers, allowing a
seamless end user experience
Support for compliance mail flow
scenarios (centralized transport)

51. On-premises Exchange organization
Existing Exchange environment
Exchange 2007 or later
Office 365 Active
Directory synchronization
Exchange 2013
Client Access &
Mailbox server
Office 365
User, contacts, & groups via Azure AD Sync
Secure mail flow
Mailbox data via Mailbox Replication Service (MRS)
Sharing (free/busy, Mail Tips, Archive, PF, etc.)

52. Hybrid deployment process
Sign up for
Office 365
Register
your
domains
with Office
365
Deploy
Office 365
Directory
Sync
Install
Exchange
2013 CAS &
MBX
Servers
(Edge opt)
Publish the
CAS Server
(Assign SSL
certificate,
firewall
rules)
Run the
Hybrid
Wizard
Exchange specific deployment
tasks (deep dive on next slide)
General Office 365 deployment tasks

53. autodiscover.contoso.com
mail.contoso.com
E2010 or
2007 Hub
E2010 or
2007 CAS
E2010 or 2007 MBX
E2013 CAS
E2013 MBX
E2013 EDGE Exchange 2010 or 2007 Servers
Intranet site
SP3/RU10 SP3/RU10
Internet-facing site
1. Prepare
Install Exchange SP and/or updates across the ORG
Prepare AD with E2013 schema
2. Deploy Exchange 2013 servers
Install both E2013 MBX and CAS servers
Set an ExternalUrl & enable MRSProxy on the Exchange Web
Services vdir
3. Obtain and deploy Certificates
Obtain and deploy certificates on E2013 CAS servers & E2010
servers
4. Publish protocols externally
Create public DNS A records for the EWS and SMTP
endpoints
Validate using Remote Connectivity Analyzer
5. Switch autodiscover namespace to E2013 CAS
Change the public autodiscover DNS record to resolve to
E2013 CAS
6. Run the Hybrid Configuration Wizard
7. Move mailboxes
EWS SMTP
From an existing Exchange 2007 or 2010 environment

54. On-Premises Exchange
Hybrid Configuration Engine
Desired
state
Internet
Step 5
Exchange
Management
Tools
Organization Level
Configuration
Objects
(Exchange Federation Trust,
Organization Relationship,
Forefront Inbound
Connector, & Forefront
Outbound Connector)
Domain Level
Configuration
Objects
(Accepted Domains &
Remote Domains)
Hybrid
Configuration
Object
Exchange Server Level
Configuration
(Mailbox Replication Service
Proxy, Certificate Validation,
Exchange Web Service
Virtual Directory Validation,
& Receive Connector)
Domain Level
Configuration Objects
(Accepted Domains,
Remote Domains, &
E-mail Address Policies)
Organization Level
Configuration Objects
(Exchange Federation Trust,
Organization Relationship,
Availability Address Space,
& Send Connector)
1
2 4 5
5
4
Step 1 The Update-HybridConfiguration
cmdlet triggers the Hybrid
Configuration Engine to start.
Based on the desired state,
topology data, and current
configuration, across both the
on-premises Exchange and
Exchange Online organizations,
the Hybrid Configuration Engine
establishes the “difference” and
then executes configuration tasks
to establish the “desired state.”
Step 4 The Hybrid Configuration
Engine discovers topology data
and current configuration from
the on-premises Exchange
organization and the Exchange
Online organization.
Step 3 The Hybrid Configuration Engine
connects via Remote PowerShell
to both the on-premises and
Exchange Online organizations.
Step 2 The Hybrid Configuration Engine
reads the “desired state” stored
on the HybridConfiguration
Active Directory object.
Remote
Powershell
Remote
Powershell
3
3

57. Exchange Admin Center (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)
Support for a merged recipient
views for helpdesk staff

60. External recipient
DAVID
On-premises mailbox
Exchange
CHRIS
Cloud mailbox
Third Party Email
Security System
Secure Mail
Encrypted &
authenticated mail flow

61. All email between Exchange on-premises and Exchange Online is encrypted and authenticated
Internal mail flow going from Exchange to Exchange must go direct and not through 3rd party
gateways
External (Internet) mail can be routed to wherever you choose – on premises, 3rd party service,
EOP
The MX record for the domain controls where inbound external email is received
The hybrid wizard’s “OnPremisesSmartHost” property controls the flow of internal mail from
Exchange Online to Exchange on-premises
The FQDN defined within OnPremisesSmartHost can be:
A single Exchange 2013 CAS or 2010 Edge server
Multiple round robin Exchange 2013 CAS or 2010 Edge servers
Multiple load balanced Exchange 2013 CAS or 2010 Edge servers (recommended)

63. Exchange Topologies Supported
Exchange 2013 RTM
Single Forest Model: Accounts and Mailboxes in
single forest
Resource Forest Model: Multiple Account
Forests, Single Resource Forest
1:1 relationship between Exchange Organization
and single O365 tenant
Exchange 2013 Service Pack 1
Supports multiple Exchange Organizations
configured against a single O365 tenant
Multiple forests, each containing accounts and
Exchange organizations
Multi-Org Hybrid Support
N:1 relationship between Exchange Organization
and single O365 tenant
Office 365
Hybrid
Office 365
Hybrid Hybrid
contoso.com fabrikam.comcontoso.com
R R R

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