What are the challenges involved with migrating to the cloud and what can you do about them? What tools can you use for deploying hybrid environment? How does a typical hybrid deployment unfold? What are some tips for managing a Hybrid Deployment? What tools can you use for monitoring & reporting on a hybrid deployment? http://www.enowsoftware.com

1. Stairway to Heaven: Best Practices for Hybrid Deployments
www.ENowSoftware.com
Michael Van Horenbeeck, Exchange MVP, MCM

2. Michael Van Horenbeeck
• Microsoft Certified Solutions Master: Messaging
• Exchange Server MVP
• Microsoft Certified Trainer
• Co-author of “Exchange 2013 Cookbook”, regular speaker at
various international events (Microsoft Exchange
Conference, Exchange Connections) and regular contributor
to “The UC Architects” and michaelvh.wordpress.com

3. What you will learn
• What are the challenges involved with migrating to
the cloud and what can you do about them?
• What tools can you use for deploying hybrid
environment?
• How does a typical hybrid deployment unfold?
• What are some tips for managing a Hybrid
Deployment?

4. When you do not plan your migration to the
cloud, things go wrong.

5. When things go wrong, your email system
will be disrupted.

6. When your email system is disrupted, your
CIO gets embarrassed.

7. When your CIO gets embarrassed, you
lose your job.

8. When you lose your job, you have to cancel
your family vacation to Disney.

9. Don’t cancel your family vacation!
Prepare for your migration to the cloud!

10. Deployment Challenges…

11. Planning
Exchange
Lotus Notes
Gmail
Yahoo
...
Source
Large
Medium
Small
Size
DirSync
Bulk Provisioning
Manual
Provisioning
On-Premises
(Single Sign-On)
On-Cloud
Identity
Management

12. Planning
• What Source?
• Tooling?
– Office 365 Migration tools?
– 3rd party tools needed?
– PST Export/Import?
– Hybrid deployment?
• Can influence migration path
– e.g. Exchange 2003 -> Office 365
IMAPmigration
Cutovermigration
Stagedmigration
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
Notes/Domino X
GroupWise X
Other X

13. What?
• What date are you moving?
• How large is the data?
• Where is it located?
• Can you reduce the amount of data?
• Infrastructure
• How much bandwidth do you have available?
• Provisioning

14. • It’s no longer only
about Exchange.
Many different teams
are involved:
– Active Directory
– Networking
– Exchange
– …
Many moving parts…

15. Implementation
Navigating your way through the migration

16. ACTIVE DIRECTORY
OFFICE 365 TENANT
EXCHANGE ONLINE
TENANT
MICROSOFT DATA CENTER INTERNET PERIMETER
NETWORK
INTERNAL NETWORK
EXCHANGE ON-PREM ORG.
AZURE AD
ADFS
PROXY
ADFS
ACTIVE
DIRECTORY
DIRSYNC
SERVER
EXCHANGE
2013
(CAS)ORGANIZATIONAL RELATIONSHIP
EXCHANGE
2013
(MBX)
ONLINE PROTECTION
HYBRID MAIL FLOW
SMTP
EXCHANGE ONLINE
AUTHENTICATION
SERVICE
EXTERNAL USER
(O365)
SYNC
HTTP(S)
HTTPS
HTTPS
OWA USER
(O365)
HTTPS
MAIL FLOW
AUTHENTICATION
SYNCHRONIZATION
APP. ACCESS (HTTP(S))
INTERNAL USER
(O365)
EXCHANGE USER
HTTPS
INTERNAL OWA USER
(O365)
16
Hybrid Architecture

17. Office 365 (v 2010) Office 365 (v 2013)
w/ On-Prem 2010
Office 365 (v 2013)
w/ On-Prem 2013
Exchange 2003 SP2 (X) (X)
Exchange 2007 SP2/SP3 (X) (X)
Exchange 2007 SP3 Urx (X) (X) (X)
Exchange 2010 SP1 X
Exchange 2010 SP2 X
Exchange 2010 SP3 X X X
Exchange 2013 N/A X
(X) = supported w/ dependencies
X = supported
Supported Topologies

18. Decisions, decisions, decisions
• High Availability?
• ADFS
• DirSync
• Hybrid Exchange environment?
• Executing the migration:
• Pilot?
• Deciding who gets in first
• Cross-premises permissions

19. “The Internet”
Deploy
Exchange
1.
Configure
SSO
(optional)
2.
Setup
DirSync
3.
Configure
Certificates
4.
Configure
WebServices
5.
Run Hybrid
Configuration Wizard
6.
Configure
MX Records
MX
7.
Deployment Process

20. Validating the deployment
• Is the environment ‘ready’?
• Is Exchange configured properly?
• Is everyone properly trained?
Visit: bit.ly/ExchangeTools for information on what tools you
can use to validate your deployment

21. Exchange
On-Prem
“The Internet”
Exchange
Online
(Office 365)
MRS
Admin
Hybrid Mailbox Moves

22. Tips for living in the cloud

23. Managing hybrid deployments
• New challenges:
• Lots of moving pieces
• What do you have to monitor?
• How to monitor cloud components?
• Complexity & lack of experience can become a problem

24. Common Issues
• Certificates
• Expired
• Not from a trusted source
• Missing/Wrong subject (alternative) name
• Single Sign-On not functioning
• Free/Busy not working properly
• Peers not recognized as “internal”
• Outlook-related (e.g. missing updates)

25. Troubleshooting steps
• Hybrid Configuration Log Files
• Review Federation Information
• Review OrganizationRelationShips
• Troubleshoot connection issues

26. Mailscape for Exchange Online
• Award Winning Software
• Used in over 50 countries
• Named Best Exchange Reporting tool for 3 years.
• Monitoring Hybrid Deployments since 2012, including:
• ADFS, DirSync, Office365 connections
• Gain visibility into Office 365, with over 30 reports,
including:
• Mailbox stats, Auditing, Mobile Devices, License
reporting.

27. Thank You
www.ENowSoftware.com