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OFFICE365
Migrating
Exchange
Dave Stork – Jetze Mellema
@dmstork – @JetzeMellema
OFFICE365
Dave Stork
• Architect @ OGD ict-diensten
• Office Servers and Services
MVP
• @dmstork
dave.stork@ogd.nl
Dirteam.com/dave
• www.practicalpowershell.com
OFFICE365
Jetze Mellema
• Consultant @ Mellema ICT
• Microsoft MVP 2005-2012
• @JetzeMellema
• jetzemellema.blogspot.com
• Tweakers, Reddit, etc.
OFFICE365
Topics
Migration scenarios
Directory synchronization
Hybrid migrations
Tenant to tenant migrations
OFFICE365OFFICE365
Introduction
OFFICE365
Migration types
• From product X to Y
• Upgrades
• Cross-forest
• Out of scope for today
OFFICE365
Let’s talk about…
• Exchange Hybrid
• Full
• Minimal
• Tenant to Tenant
• Express Migration
OFFICE365OFFICE365
But first…
OFFICE365OFFICE365
Identities and authentication
OFFICE365
Options
• Synchronization
• Provisioning
• Maintenance
• Authentication
• Where?
• SSO/Same set of credentials
OFFICE365
Office 365
Azure AD
On-premises
Active Directory
B
A
Office 365
Azure AD
On-premises
Active Directory
A
A
+ Password
Hash
Office 365
Azure AD
On-premises
Active Directory
A
A
PTA
Office 365
Azure AD
On-premises
Active Directory
A
A
ADFS
OFFICE365
Sync Tools
• FIM/MIM
• AAD Connect
• Sync engine
• Deployment
OFFICE365OFFICE365
Full Exchange Hybrid
OFFICE365
Full Hybrid
• Configured with Hybrid Configuration
Wizard
• ‘Virtual single Exchange organization’
• Best user experience
• Supports long-term coexistence
OFFICE365
Requirements
• Exchange 2010 or newer
• 3rd party trusted SSL certificate
• Directory synchronization
OFFICE365
Plaatje hybrid
OFFICE365
“Hybrid server”
• Not a server: set of configuration items
• Exchange 2010 whitepaper: 75 tasks
• HCW configures:
• Exchange on-premises
• Exchange Online
• Exchange Online Protection
OFFICE365
Upgrade first?
• Newer hybrid features required?
• Exchange 2013/2016 hybrid offers:
• OAuth
• Multi-forest to single tenant
• Hybrid modern authentication
OFFICE365
Else…
• Implement Exchange 2010 based hybrid
• Migrate mailboxes
• Update DNS records
• Upgrade to most recent hybrid
management server
OFFICE365
Mail flow: Inbound
• Two options:
• MX to on-premises
• MX to Exchange Online Protection
• EOP requires licenses
• Single MX record
OFFICE365
Mail flow: Outbound
• Two options:
• On-premises and cloud
• Centralized Mail Transport (CMT)
• Use CMT only when required
• SPF!
OFFICE365
Mail flow: Outbound
OFFICE365
Mail flow: Outbound
OFFICE365
Mail flow: cross premises
• Configured by HCW
• Send Connector/Receive connector
• Inbound/Outbound connector
• To cloud: <tenant>.mail.onmicrosoft.com
• To on-premises: <domain.tld>
OFFICE365
Mail flow: cross premises
• TLS
• Headers for coexistence features
• No 3rd party host in front:
• Route email to internal Exchange
• Or deploy Edge Transport in DMZ
OFFICE365
Exchange
On-premises
Exchange
Online
Send
Connector
Outbound
Connector
Internet
OFFICE365
Exchange org config
• New HCW feature: Hybrid Organization
Configuration Transfer
• On-time copy, not sync
• Limited set of objects, will expand
OFFICE365
OFFICE365
Exchange org config
• Phase 1:
• Retention Policy
• Retention Policy Tags
• OWA Mailbox Policy
• Mobile Device Mailbox Policy
• Active Sync Mailbox Policy
OFFICE365
Exchange org config
• Phase 2:
• More config objects
• Conflict handling
• Phase x:
• Transport rules
OFFICE365
Mailbox moves
• Mailbox Replication Service
• Batches
• Created in the cloud (pull)
• Firewall and reverse proxy:
• allow EWS/MRSProxy.svc
• SSL bridging OK, offloading not!
OFFICE365
Public Folders
• Legacy vs Modern Public Folders (PFs)
• Coexistence with EXO
• Either On-prem or Online
Scenario On-Premises
Exchange 2010 User
Mailbox
On-Premises
Exchange 2016 User
Mailbox
Exchange Online User
Mailbox
On-Premises
Exchange 2010 Public
Folders
- - Supported
On-Premises
Exchange 2013 or
Exchange 2016 Public
Folders
- - Supported
Exchange Online
Public Folders
Not supported Supported -
OFFICE365
Migrating Public Folders
• Consider converting to
• Shared/Room/Equipment mailbox
• SharePoint
• Office 365 Groups
• Process depends on on-prem Exchange
• Always batch migration & cut-over
• Extra care with Mail-Enabled PFs
OFFICE365
Long term hybrid
• Directory sync -> on-premises AD is
Source of Authority
• Keep an on-premises Exchange server
• Required to managed Exchange objects
• ADSI Edit, 3rd party tools may work, but
not supported
OFFICE365
Long term hybrid
• Hybrid recipient management
• Update object in cloud
• Replicate to on-prem
• Sync to Exchange Online
• No on-premises Exchange required
• TBD
OFFICE365OFFICE365
Minimal Hybrid
OFFICE365
Minimal Hybrid
Same as Full Hybrid
• On-prem Exchange
• Directory synchronization
• Mailbox moves
Except…
OFFICE365
Minimal Hybrid
If you do not need:
• Availability (Free/Busy)
• TLS protected Mailflow
• Cross-premises eDiscovery
• OWA & ActiveSync redirection
• Archive Mailbox Retention
OFFICE365
Minimal Hybrid
• MRS moves
• No rich coexistence
• Less configuration
OFFICE365OFFICE365
Tenant to tenant
OFFICE365
When?
• Acquisitions and mergers
• Tenant name change
• Region change
OFFICE365
Challenges
• Which workload(s)
• Which tool(s)
• Identities and authentication
• Licenses
• Mail flow
OFFICE365
DNS domains
• Can exist in only one tenant
• Add to second tenant
• Add validation DNS record
• Remove from first tenant
• Finalize in second tenant
OFFICE365
Recommendations
• Understand your data
• Understand the tooling
• Plan and test
• Plan for downtime and manual tasks
OFFICE365OFFICE365
Express Migration
OFFICE365
Express Migration
• Minimal migration scenario
• Configured with Hybrid Configuration
Wizard
• One-time directory sync
• Limited coexistence (mail flow)
• Multiple migration batches
OFFICE365
Express Migration
• Use only when NO need for:
• Directory synchronization
• On-prem mail flow
• Public Folder migration
OFFICE365
Express Migration
• No recreation of Outlook Profile
• No downtime
• Ideal when going cloud-only
• Less configuration
• Replaces staged and cut-over
OFFICE365OFFICE365
In summary
OFFICE365
What to choose?
• Full Hybrid: best experience
• Minimal Hybrid: less configuration
• Express Migration: no dir sync
OFFICE365
Tenant to tenant
• Plan and prepare
• Know what you’re about to migrate
• Know how you’re about to migrate
• Do not underestimate
OFFICE365OFFICE365
Resources
OFFICE365
References
Microsoft Exchange Server Deployment Assistant
Office 365 URLs and IP address ranges
How to set up a multifunction device or application to send email
using Office 365
Organization Configuration Transfer Attributes
Hybrid Identity directory integration tools comparison
PAW your way into Office 365 Migrations
Overview of delegation in an Office 365 hybrid environment
OFFICE365
References
HCW Improvement: The Minimal Hybrid Configuration option
Understanding Office 365 identity and Azure Active Directory
Set up SPF in Office 365 to help prevent spoofing
OFFICE365
See you next year!

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