1. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Deploying Exchange 2016
On-premises and hybrid

2. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
@enowconsulting
Find us!
ENow Software
ENowSoftware
ENowSoftware.com
Some of ENow’s Loyal Customers
• Microsoft Silver ISV & Messaging Microsoft Partner
• Focused on building software solutions that simplify the life of IT administrators
• Software architected by MVPs with >15 years experience in high-end Microsoft
consulting and management
• Customers in over 60 countries ENow Software
About ENow

3. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T

4. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Speaker Introduction
• Director of Product
Research at ENow
Software
• Exchange Server MVP
• Certified Solutions Master
Messaging (MCSM)
Twitter: @mvanhorenbeeck
Blogs: blog.enowsoftware.com, vanhybrid.com

5. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Please save your questions
for the end of the
presentation.
We will be giving away two
“Office 365 for Exchange
Professionals” e-books for our
favorite questions!
Ask & Win!

6. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Agenda
Deploying Exchange 2016 on-premises
Exchange 2016 in a hybrid world

7. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Disclaimer
Anything I say only applies to Exchange 2016 in its current
form (October 27, 2015). Given the high-paced rate of
change (updates) to Exchange and Office 365, some
elements from this presentation are likely to change and
look different in the (near) future.

8. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
On-premises

9. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Exchange 2016 or not?
• If you are running Exchange 2010, upgrading to Exchange
2016 makes a lot of sense.
• If you are running Exchange 2013, upgrading to Exchange
2016 is nice, but not really necessary. Unless…
…which aren’t available yet!
… you want to take advantage of some
really cool new collaboration features…

10. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Know before you go!
You cannot mix and match Exchange 2013/2016
mailbox servers in a single DAG
Outlook 2007 is NOT supported
You cannot migrate from Exchange 2003 (shame on
you!) or Exchange 2007; double-hop is required then.

11. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Prerequisites
Active Directory: Windows Server 2008 (or higher) Domain
Functional Level / Forest Functional Level
Windows Server 2012 (or higher)
.NET Framework 4.5.2
Unified Communication Management API 4.0
OS-level requirements

12. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Coexistence
Server-side
• Exchange 2010 Service
Pack 3 Update-Rollup 11
• Exchange 2013 Cumulative
Update 10
Client-Side
• Outlook 2010 Service Pack
2 (or higher)
• Outlook for Mac 2011 (or
higher)

13. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Planning
• Exchange 2016 Role Requirements calculator (recently
updated)
• Exchange 2016 Preferred Architecture
• Exchange Deployment Assistant (aka.ms/exdeploy)

14. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Preferred Architecture
• Unbound namespace model
• Namespace per “protocol” (HTTP, POP, IMAP, SMTP)
• Load balancing w/ equal distribution across datacenters
(ie DNS RR)
• Physical Servers 
• Two Office Servers per DC (when available, of course)

15. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
‘NEW’ Recommendations
• Enable Bitlocker for disk encryption; protect against data
theft (physical disk)
• Data Volumes should use ReFS (w/ data integrity features
disabled)
• Interesting article by Exchange MVP Michel de Rooij on ReFS
performance vs. NTFS

16. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Exchange 2010 Interoperability
Down-level proxying only! (or redirect)
Ex2016
MBX
Ex2010
CAS
Site A Site B
Ex2010
CAS

17. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Exchange 2013 Interoperability
Up-level proxying Down-level proxying
Ex2013
CAS
Ex2016
MBX
Ex2016
MBX
Ex2013
MBX

18. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Cert Namespaces w/ 2010
Unbound Namespace
• Autodiscover (1)
• General Namespace (1)
• Internal URL (1)
• 2 Office Web Apps URLs
per DC (4)
Bound Namespace
• Autodiscover (1)
• General Namespace (1)
• External URL per DC (2)
• Internal URL per DC (2)
• Failback URLs per DC (2)
• 2 Office Web Apps URLs
per DC (4)

19. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Cert Namespaces w/ 2013
Unbound Namespace
• Autodiscover (1)
• General Namespace (1)
• Internal URL (1)
• 2 Office Web Apps URLs
per DC (4)
Bound Namespace
• Autodiscover (1)
• General Namespace (1)
• External URL per DC (2)
• Internal URL per DC (2)
• 2 Office Web Apps URLs
per DC (4)

20. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Cert Namespaces in 2016-only
Unbound Namespace
• Autodiscover (1)
• General Namespace (1)
• Internal URL (1)
• 2 Office Web Apps URLs
per DC (4)
Bound Namespace
• Autodiscover (1)
• General Namespace (1)
• External URL per DC pair (2)
• Internal URL per DC pair (2)
• 2 Office Web Apps URLs
per DC (4)

21. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Load Balancing
• No specific load-balancing requirements; can use Layer 4
or Layer 7 load balancing (same as Exchange 2013)
• If you use a load balancer, use it smart
• Leverage Managed Availability where possible
(healthcheck.htm)
• Delayed start to avoid servers being overrun when added to the
“pool”

22. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Pre-deployment tasks
• Configure Exchange 2010 Outlook Anywhere; include
NTLM on the IIS Authentication Methods
• Define existing OAB on existing DBs prior to installing
Exchange 2016 to avoid all clients downloading new
default OAB (Ex2016/2013 create new default OAB as part
of setup)
• Re-run Edge subscriptions (if any)

23. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Installing Exchange 2016
• Setup is pretty straightforward… but do not forget to
/IacceptExchangeServerLicenseTerms ;-)
1
2
Install Prerequisites. Reboot.
• Consider using Exchange Server MVP
Michel de Rooij’s Unattended Installation script
• Consider using a ‘staging AD site’ to avoid interference with
operations; if not – configure/remove SCP right after installation!
Install Exchange 2016 (GUI or CLI). Reboot.
High-Level process:

24. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Cutting over to Exchange 2016
• The process of “switching” over to Exchange 2016 is
different, depending on what version of Exchange you are
migrating from.
• You can switch over mail flow (SMTP) at any time
during/after the migration;
• Typically done when 50% (or more) of the users are migrated

25. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Post-Installation tasks
• Do not to configure Autodiscover/set the SCP to avoid
cert pop-ups etc…
• Move system mailbox from legacy version to 2016 to allow
the following to work properly:
• Admin Audit Logging
• eDiscovery Searches
• New 2016 functionality

26. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Hybrid

27. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Should you upgrade?
Exchange
Version?
Use Exchange 2013 or
2016 HCW
Migration only
or Coexistence?
Do you need
new features?
Really?
Use Exchange 2010
HCW
2010
2013/2016
CoexistenceMigration
No
No
Yes
Yes

28. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Exchange 2016 Hybrid
• The ‘new’ Hybrid Configuration Wizard offers Microsoft
more flexibility; you are always running the latest version
• Must be run from an Exchange 2016 server;
• Downloads components onto the server from
configure.office.com

29. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Hybrid namespace?
Office365
Autodiscover hybrid.domain.com
Ex2016
Ex2010
• Not supported…!
• Chances are you will switch over in the
future anyway
• Added complexity = higher change to
failure/issues!

30. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Mailscape
Fully supports Exchange 2016 

31. A W A R D W I N N I N G E X C H A N G E M A N A G E M E N T
Q&A