Migrating From Exchange 2010 To 2016 PDF

Migrating from Exchange
2010 to 2016 – Step by Step

Volume 1
Dave Kawula - MVP

Cary Sun – Cisco Champion (CCIE)
PUBLISHED BY
MVPDays Publishing
http://www.mvpdays.com
Copyright © 2018 by MVPDays Publishing
All rights reserved. No part of this book may be reproduced or transmitted in any form or by any
means without the prior written permission of the publisher.
ISBN: TBA
Warning and Disclaimer

Every effort has been made to make this manual as complete and as accurate as possible, but no
warranty or fitness is implied. The information provided is on an “as is” basis. The authors and
the publisher shall have neither liability nor responsibility to any person or entity with respect to
any loss or damages arising from the information contained in this book.
Feedback Information
We’d like to hear from you! If you have any comments about how we could improve the quality
of this book, please don’t hesitate to contact us by visiting www.checkyourlogs.net or sending an
email to feedback@mvpdays.com.
Acknowledgements
iii
Acknowledgements
Acknowledgements
From Dave
Cristal, you are my rock and my source of inspiration. For the past 20 + years you have been
there with me every step of the way. Not only are you the “BEST Wife” in the world you are my
partner in crime. Christian, Trinity, Keira, Serena, Mickaila and Mackenzie, you kids are so patient
with your dear old dad when he locks himself away in the office for yet another book. Taking the
time to watch you grow in life, sports, and become little leaders of this new world is incredible to
watch.
Thank you, Mom and Dad (Frank and Audry) and my brother Joe. You got me started in this crazy
IT world when I was so young. Brother, you mentored me along the way both coaching me in
hockey and helping me learn what you knew about PC’s and Servers. I’ll never forget us as
teenage kids working the IT Support contract for the local municipal government. Remember
dad had to drive us to site because you weren’t old enough to drive ourselves yet. A great
career starts with the support of your family and I’m so lucky because I have all the support one
could ever want.
A book like this filled with amazing Canadian MVP’s would not be possible without the support
from the #1 Microsoft Community Program Manager – Simran Chaudry. You have guided us
along the path and helped us to get better at what we do every day. Your job is tireless and
your passion and commitment make us want to do what we do even more.
Last but not least, the MVPDays volunteers, you have donated your time and expertise and
helped us run the event in over 20 cities across North America. Our latest journey has us
expanding the conference worldwide as a virtual conference. For those of you that will read this
book your potential is limitless just expand your horizons and you never know where life will take
you.
iv
About the Authors
About the Authors

Dave Kawula - MVP
Dave is a Microsoft Most Valuable Professional (MVP) with over 20 years of experience in the IT
industry. His background includes data communications networks within multi-server
environments, and he has led architecture teams for virtualization, System Center, Exchange,
Active Directory, and Internet gateways. Very active within the Microsoft technical and
consulting teams, Dave has provided deep-dive technical knowledge and subject matter
expertise on various System Center and operating system topics.
Dave is well-known in the community as an evangelist for Microsoft, 1E, and Veeam
technologies. Locating Dave is easy as he speaks at several conferences and sessions each year,
including TechEd, Ignite, MVP Days Community Roadshow, and VeeamOn.
Recently Dave has been honored to take on the role of Conference Co-Chair of TechMentor with
fellow MVP Sami Laiho. The lineup of speakers and attendees that have been to this conference
over the past 20 years is really amazing. Come down to Redmond or Orlando in 2018 and you
can meet him in person.
As the founder and Managing Principal Consultant at TriCon Elite Consulting, Dave is a leading
technology expert for both local customers and large international enterprises, providing optimal
guidance and methodologies to achieve and maintain an efficient infrastructure.
BLOG: www.checkyourlogs.net
Twitter: @DaveKawula
v
Cary Sun – CCIE #4531
Cary Sun is CISCO CERTIFIED INTERNETWORK EXPERT (CCIE No.4531) and MCSE, MCIPT, Citrix
CCA with over twenty years in the planning, design, and implementation of network technologies
and Management and system integration. Background includes hands-on experience with multi-
platform, all LAN/WAN topologies, network administration, E-mail and Internet systems, security
products, PCs and Servers environment. Expertise analyzing user’s needs and coordinating
system designs from concept through implementation. Exceptional analysis, organization,
communication, and interpersonal skills. Demonstrated ability to work independently or as an
integral part of team to achieve objectives and goals. Specialties: CCIE /CCNA / MCSE / MCITP /
MCTS / MCSA / Solution Expert / CCA
Cary’s is a very active blogger at checkyourlogs.net and always available online for questions
from the community. He passion about technology is contagious and he makes everyone around
him better at what they do.
Blog:http://www.checkyourlogs.net
Twitter:@SifuSun
vi
Technical Editors
Cristal Kawula – MVP
Cristal Kawula is the co-founder of MVPDays Community Roadshow and #MVPHour live Twitter
Chat. She was also a member of the Gridstore Technical Advisory board and is the President of
TriCon Elite Consulting. Cristal is also only the 2nd Woman in the world to receive the prestigious
Veeam Vanguard award.
Cristal can be found speaking at Microsoft Ignite, MVPDays, and other local user groups. She is
extremely active in the community and has recently helped publish a book for other Women
MVP’s called Voices from the Data Platform.
BLOG: http://www.checkyourlogs.net
Twitter: @supercristal1
vii
Emile Cabot - MVP

Emile started in the industry during the mid-90s working at an ISP and designing celebrity web
sites. He has a strong operational background specializing in Systems Management and
collaboration solutions, and has spent many years performing infrastructure analyses and
solution implementations for organizations ranging from 20 to over 200,000 employees.
Coupling his wealth of experience with a small partner network, Emile works very closely with
TriCon Elite, 1E, and Veeam to deliver low-cost solutions with minimal infrastructure
requirements.
He actively volunteers as a member of the Canadian Ski Patrol, providing over 250 hours each
year for first aid services and public education at Castle Mountain Resort and in the community.
BLOG: http://www.checkyourlogs.net
Twitter: @ecabot
viii
ix
Contents
Contents
Acknowledgements ...................................................................................................... iv
From Dave ............................................................................................................. iv
About the Authors ......................................................................................................... v

Dave Kawula - MVP ..................................................................................................... v
Cary Sun – CCIE #4531 ................................................................................................ vi

Technical Editors ....................................................................................................... vii
Cristal Kawula – MVP ............................................................................................ vii
Emile Cabot - MVP ............................................................................................... viii
Contents......................................................................................................................... x
Introduction ................................................................................................................. 14
North American MVPDays Community Roadshow ................................................... 14

Sample Files ............................................................................................................. 15
Additional Resources ................................................................................................ 15
Chapter 1...................................................................................................................... 17
Exchange 2016 Design Guidance............................................................................... 17

Exchange 2016 System requirements ...................................................................... 19
Coexistence of Exchange 2016 with earlier versions of Exchange Server ............ 19
Network and directory server requirements for Exchange 2016 ........................... 20
Supported operating systems for Exchange 2016 ................................................ 20
x
Contents
.NET Framework .................................................................................................. 21

Supported clients ................................................................................................. 22
Chapter 2...................................................................................................................... 23
Exchange 2016 Prerequisites ..................................................................................... 23

Exchange 2016 Mailbox Server Role Prerequisites .................................................. 23
Follow steps to install prerequisites for Windows Server 2016 ............................. 23
Follow steps to install prerequisites for Windows Server 2012 R2 ........................ 27
Prepare Active Directory ........................................................................................... 29
Chapter 3...................................................................................................................... 36
Deploy Exchange Server 2016 Mailbox Role Server ................................................. 36

Deployment of Certificates ........................................................................................ 39
Chapter 4...................................................................................................................... 56
Configure Exchange Server 2016 ............................................................................... 56

Verify Existing Client Access Namespaces ............................................................... 56
Configuring the Autodiscover Services Connection Point (SCP) for Exchange 2016
Server .................................................................................................................. 64
Configuring the Client Access Namespaces for Exchange 2016 Server ............... 65
Testing the Client Access Namespaces ............................................................... 66
Cut Over the Client Access namespace to Windows 2016 ................................... 67
Configuring New Offline Address Book for Exchange 2016 Server....................... 69
Configuring Receive Connectors for Exchange 2016 server................................. 71
Change Outbound Mail flow Routing (Send Connectors) ..................................... 77
Chapter 5...................................................................................................................... 80
Connectivity and Mail Flow Test ................................................................................ 80

xi
Contents
Outlook Connectivity Test..................................................................................... 80

Outlook Autodiscover Connectivity Test ............................................................... 84
Exchange ActiveSync Connectivity Test............................................................... 86
Exchange ActiveSync Autodiscover Connectivity Test ......................................... 92
Exchange Web Services Connectivity Test – Synchronization, Notification,
Availability, and Automatic Replies ....................................................................... 94
Testing Inbound Mail Flow.................................................................................... 95
Testing Outbound Mail Flow ............................................................................... 100
Chapter 6.................................................................................................................... 104
Post-Configuration Steps ......................................................................................... 104

Configuring the Default Mailbox Database for Exchange Server 2016 .................... 104
Create a New Mailbox Database ........................................................................ 106
Configuring Mailbox Database Quota ................................................................. 107
Configuring Offline Address Book....................................................................... 108
Migrate Arbitration Mailboxes ............................................................................. 109
Chapter 7.................................................................................................................... 112
Mailbox Migration ...................................................................................................... 112

Migrate Pilot mailboxes via Exchange Administrative Center ............................. 112
Chapter 8.................................................................................................................... 118
Public Folder Migration ............................................................................................. 118
Contact Us ................................................................................................................. 140
Join us at MVPDays and meet great MVP’s like this in person .............................. 140
Live Presentations .................................................................................................. 140
Video Training......................................................................................................... 140
xii
Contents
Live Instructor-led Classes ...................................................................................... 141

Consulting Services ................................................................................................ 141
Twitter ..................................................................................................................... 142
xiii
Introduction North American MVPDays Community Roadshow
Introduction
North American MVPDays

Community Roadshow
The purpose of this book is to showcase the amazing expertise of our guest speakers at the
North American MVPDays Community Roadshow. They have so much passion, expertise, and
expert knowledge that it only seemed fitting to write it down in a book.
MVPDays was founded by Cristal and Dave Kawula back in 2013. It started as a simple idea;
“There’s got to be a good way for Microsoft MVPs to reach the IT community and share their
vast knowledge and experience in a fun and engaging way” I mean, what is the point in
recognizing these bright and inspiring individuals, and not leveraging them to inspire the
community that they are a part of.
We often get asked the question “Who should attend MVPDays”?
Anyone that has an interest in technology, is eager to learn, and wants to meet other like-
minded individuals. This Roadshow is not just for Microsoft MVP’s it is for anyone in the IT
Community.
Make sure you check out the MVPDays website at: www.mvpdays.com. You never know maybe
the roadshow will be coming to a city near you.
The goal of this particular book is to show you how to Migrate your legacy Exchange 2010
environment to Exchange 2016. We built based on our experience migrating live customer
environments.
14
Sample Files
All sample files for this book can be downloaded from www.checkyourlogs.net and
www.github.com/dkawula
Additional Resources
In addition to all tips and tricks provided in this book, you can find extra resources like articles
and video recordings on our blog http://www.checkyourlogs.net.
15
16
Chapter 1 Exchange 2016 Design Guidance
Chapter 1
Exchange 2016 Design

Guidance
This document serves as both a guideline for redeployment document for the Exchange
Migration performed at the [Company]. The information within will be primarily prescriptive,
but will include annotations of any issues encountered, as well as any issues that might arise
should the need to redeploy occur.
The process described mainly focuses on a typical transition of Exchange 2010 to Exchange 2016
environment, converting the Exchange 2010 server to Exchange 2016 Server MBX role.
Additional role options such as the Unified Messaging Server role and Edge Transport role, are
out-of-scope within this document.
17
Current State Feature State
Internet
Internet
Internal corporate network
Exchange
2010 servers
Internal corporate network
Exchange Exchange Exchange

2010 MBX 2010 CAS/
server HUB server 2016 Server
Active On-premises Active Directory

On- Directory users Domain Services
premises Domain
users Services
18
Exchange 2016 System requirements
Coexistence of Exchange 2016 with earlier versions of Exchange

Server
Exchange version Exchange organization coexistence
Exchange 2007 and earlier versions Not supported
Exchange 2010 Supported with Update Rollup 11 for Exchange 2010 SP3
or later on all Exchange 2010 servers in the organization,
including Edge Transport servers.
Exchange 2013 Supported with Exchange 2013 Cumulative Update 10 or

later on all Exchange 2013 servers in the organization,
Mixed Exchange 2010 and Supported with the following minimum versions of
Exchange 2013 organization Exchange:
 Update Rollup 11 Exchange 2010 SP3 or later on

all Exchange 2010 servers in the organization,
 Exchange 2013 Cumulative Update 10 or later on
all Exchange 2013 servers in the organization,
19
Network and directory server requirements for Exchange 2016
Component Requirement
Domain controllers All domain controllers in the forest need to be running one
of the following:
 Windows Server 2016 Standard or Datacenter
 Windows Server 2012 R2 Standard or Datacenter
 Windows Server 2008 R2 Standard or Enterprise
 Windows Server 2008 R2 Datacenter RTM or later
 Windows Server 2008 Standard, Enterprise, or

Datacenter
Active Directory forest The Active Directory forest functionality level needs to be
at Windows Server 2008 or higher.
Supported operating systems for Exchange 2016
Component Requirement
Mailbox and Edge Transport server  Windows Server 2016 Standard or Datacenter
roles (Requires Exchange Server 2016 Cumulative
Update 3 or later)
20
Management tools  Windows Server 2016 Standard or Datacenter*
 64-bit edition of Windows 10
 64-bit edition of Windows 8.1
.NET Framework
Exchange version .NET Framework 4.6.2 .NET Framework 4.6.1 .NET Framework 4.5.2
Exchange 2016 CU5 V Not supported Not supported

or later
Exchange 2016 CU4 V V V
(Starting with (Starting with

Exchange 2016 CU5, Exchange 2016 CU5,
.NET Framework 4.6.1 .NET Framework 4.6.1
and 4.5.2 will no and 4.5.2 will no
longer be supported longer be supported
with Exchange 2016. with Exchange 2016.
While those versions While those versions
of .NET Framework of .NET Framework
are supported by are supported by
Exchange 2016 CU4, Exchange 2016 CU4,
we strongly we strongly
recommend that you recommend that you
upgrade servers upgrade servers
running Exchange running Exchange
2016 to .NET 2016 to .NET
Framework 4.6.2.) Framework 4.6.2.)
21
Exchange 2016 CU3 V V V
Exchange 2016 CU2 Not supported V V
(.NET Framework
4.6.1 requires post-
release fixes if you
want to install it on a
server running
Exchange 2016 CU2.)
(If you're upgrading to

Exchange 2016 CU4
from Exchange 2016
RTM, CU1, or CU2, we
strongly recommend
that you install
Exchange 2016 CU4
before .NET
Framework 4.6.2 or
.NET Framework 4.6.1
and its related post-
release fixes)
Exchange 2016 RTM Not supported Not supported V

or CU1
Supported clients
 Outlook 2016
 Outlook 2013
 Outlook 2010 SP2 and updates KB2956191 and KB2965295
 Outlook for Mac for Office 365
 Outlook for Mac 2011
22
Chapter 2 Exchange 2016 Prerequisites
Chapter 2
Exchange 2016 Prerequisites

Exchange 2016 Mailbox Server Role
Prerequisites
Follow steps to install prerequisites for Windows Server 2016
1. Login to Windows Server 2016 server.

2. Open Windows PowerShell as administrator
3. Run cmdlet as follow:
Install-WindowsFeature NET-Framework-45-Features, RPC-over-HTTP-proxy,

RSAT-Clustering, RSAT-Clustering-CmdInterface, RSAT-Clustering-Mgmt,
RSAT-Clustering-PowerShell, Web-Mgmt-Console, WAS-Process-Model, Web-Asp-
Net45, Web-Basic-Auth, Web-Client-Auth, Web-Digest-Auth, Web-Dir-
Browsing, Web-Dyn-Compression, Web-Http-Errors, Web-Http-Logging, Web-
Http-Redirect, Web-Http-Tracing, Web-ISAPI-Ext, Web-ISAPI-Filter, Web-
Lgcy-Mgmt-Console, Web-Metabase, Web-Mgmt-Console, Web-Mgmt-Service, Web-
Net-Ext45, Web-Request-Monitor, Web-Server, Web-Stat-Compression, Web-
Static-Content, Web-Windows-Auth, Web-WMI, Windows-Identity-Foundation,
RSAT-ADDS
23
4. Download and Install .NET Framework 4.6.2
24
Note
You can check for a minimum-required .NET Framework version by querying the
registry in PowerShell (.NET Framework 4.5 and later).
Get-ChildItem “HKLM:SOFTWARE\MICROSOFT\NET Framework

SETUP\NDP\V4\FULL\” | Get-ItemPropertyValue -Name Release | ForEach-Object {
$_ -ge 394802 }
You can replace 394802 in the previous example with another value from the following
table to check for a different minimum-required .NET Framework version.
Minimum value of the Release

Version
DWORD
.NET Framework
378389
4.5
.NET Framework
378675
4.5.1
.NET Framework
379893
4.5.2
.NET Framework
393295
4.6
.NET Framework
394254
4.6.1
.NET Framework
394802
4.6.2
25
.NET Framework
460798
4.7
.NET Framework
461308
4.7.1
5. Download and install Microsoft Unified Communications Managed API 4.0, Core Runtime
64-bit
26
Follow steps to install prerequisites for Windows Server 2012 R2
1. Login Windows Server 2012 R2 Server.

2. Open Windows PowerShell as administrator
3. Run cmdlet as follow:
Install-WindowsFeature AS-HTTP-Activation, Server-Media-Foundation, NET-

Framework-45-Features, RPC-over-HTTP-proxy, RSAT-Clustering, RSAT-
Clustering-CmdInterface, RSAT-Clustering-Mgmt, RSAT-Clustering-
PowerShell, Web-Mgmt-Console, WAS-Process-Model, Web-Asp-Net45, Web-
Basic-Auth, Web-Client-Auth, Web-Digest-Auth, Web-Dir-Browsing, Web-Dyn-
Compression, Web-Http-Errors, Web-Http-Logging, Web-Http-Redirect, Web-
Http-Tracing, Web-ISAPI-Ext, Web-ISAPI-Filter, Web-Lgcy-Mgmt-Console,
Web-Metabase, Web-Mgmt-Console, Web-Mgmt-Service, Web-Net-Ext45, Web-
Request-Monitor, Web-Server, Web-Stat-Compression, Web-Static-Content,
Web-Windows-Auth, Web-WMI, Windows-Identity-Foundation, RSAT-ADDS
4. Download and Install .NET Framework 4.6.2
Note
Exchange 2016 CU5 and later require .NET Framework 4.6.2.
Upgrade your servers to .NET Framework 4.6.2 before you install
Exchange 2016 CU5 or you'll receive an error. If .NET Framework
4.5.2 is installed on your Exchange servers, upgrade your servers
to Exchange 2016 CU4 before installing .NET Framework 4.6.2.
5. Download and install Microsoft Unified Communications Managed API 4.0, Core Runtime
64-bit
27
28
Prepare Active Directory
Follow steps to check Active Directory and make sure they are meet the requirements in
Exchange 2016 system requirements.
1. Download Get-ADinfo.ps1 PowerShell script from follow link and save to c:\post-install:
https://github.com/cunninghamp/Powershell-Exchange/tree/master/ADInfo
2. Login exchange 2016 server, the account needs to be a member of the Schema Admins
and Enterprise Admins security groups.
3. Open PowerShell as administrator and run Get-ADinfo.ps1
29
4. Review all of information and mare sure they are meet the requirements in Exchange
2016 system requirements.
30
Note
You also can use cmdlet as follow to check the Active Directory and Domain Controller
information.
Get-ADForest
Get-ADDomainController | Select Name,OperatingSystem
5. Download Cumulative Update 7 for Exchange Server 2016 (KB4018115) from link
https://www.microsoft.com/en-us/download/details.aspx?id=55953
31
6. Open a Windows Command Prompt as administrator and go to Exchange Server 2016

Cumulative Update 7 installation file folder.
7. Run the following command to extend the schema.
Setup.exe /PrepareSchema /IAcceptExchangeServerLicenseTerms
8. Run the following command to Prepare Active Directory.
Setup.exe /PrepareAD /IAcceptExchangeServerLicenseTerms
32
9. Run the following command to Prepare Active Directory domains
Setup.exe /PrepareAllDomains /IacceptExchangeServerLicenseTerms
33
10. You can review settings via ADSI EDIT tool and make sure everything is correct.
Exchange rangeUpper objectVersion objectVersion

version
Naming Schema Default Configuration

context
Container ms-Exch- Microsoft CN=<your

Schema- Exchange System organization>,
Version-Pt Objects CN=Microsoft
Exchange,
CN=Services,
CN=Configuration,
DC=<domain>
13236
Exchange 15332 16213
2016 CU7
34
13236
2016 CU6
13236
2016 CU5
13236
2016 CU4
13236
2016 CU3
13236
2016 CU2
13236
2016 CU1
13236
2016 RTM
13236
2016 Preview
35
Chapter 3 Deploy Exchange Server 2016 Mailbox Role Server
Chapter 3
Deploy Exchange Server 2016

Mailbox Role Server
1. Login exchange 2016 server

2. Open Windows command prompt as administrator
3. Run follow command to install Exchange Server 2016 Mailbox Role
Setup.exe /mode:Install /r:MB /IAcceptExchangeServerLicenseTerms
36
37
Note
Please make sure you are using the correct .Net Framework with
exchange 2016 version. It will happen error message as follow when they are
not match.
4. Restart exchange 2016 server after deployment finish.
38
Deployment of Certificates
We can re-use existing SSL certificate for new Exchange 2016 server.
1. Logon to Exchange 2010 Server.
2. Go to Exchange Management Console, expand Microsoft Exchange On-Premises.
3. In the Console tree, click Server Configuration.
4. Select exchange CAS/HUB server and click certificate which use for exiting exchange
services.
5. On the Action pane select Export Exchange Certificate….
39
6. On the Export Exchange Certificate page, click Browse...
7. On the Save As page, select path and type file name and then click Save.
40
8. On Export Exchange Certificate page, type password and then click Export.
41
9. On the Completion page, click Finish.
42
10. Copy certificate file from exchange 2010 server to exchange 2016 server.
11. Login to Exchange 2016 server.
12. Open Exchange Administrative Center, select Continue to this website (not
recommended).
43
13. On the Exchange Admin Center page, type user name and password and then click sign
in.
14. On the Exchange admin center page, click servers.
44
15. Select certificates and then click and then select Import Exchange Certificate.
16. On the import Exchange certificate page, type certificate file name from a UNC path
and password and then click Next.
45
17. On the Specify the servers where you want to install the certificate page, click +.
46
18. Select server form list, click add and then click OK.
47
19. On the Specify the servers where you want to install the certificate page, click Finish.
48
49
Note
Run follow cmdlet to use the Exchange Management Shell to import a
certificate on an Exchange server.
Import-ExchangeCertificate -FileName \\localhost\c$\post-
install\certificate\gdmexternal.pfx -Password (ConvertTo-
SecureString -String 'super$2013' -AsPlainText -Force) -
PrivateKeyExportable $true -Server GDMEX02
You need to write down the Thumbprint if you would like to assign exchange
services for this certificate via cmdlet.
20. On the certificates page, select new add certificate and the click .
50
21. Select services, click SMTP, IIS (specify the exchange services that you want to assign
this certificate) and then click Save.
51
22. On the Warning page, click Yes.
52
53
Note
Run follow cmdlet to use the Exchange Management Shell to assign
Exchange services to a certificate on an Exchange server.
Enable-ExchangeCertificate -Thumbprint
E6195C7F197AAD4C3E087C976EB9B0BC744D21C5 -Services SMTP,IIS -
Server GDMEX02
Run follow cmdlet to verify that you have successfully assigned a certificate to one
or more Exchange services.
Get-ExchangeCertificate | Format-List
FriendlyName,Subject,CertificateDomains,Thumbprint,Services
54
55
Chapter 4 Configure Exchange Server 2016
Chapter 4
Configure Exchange Server

2016
Verify Existing Client Access Namespaces

It’s a good time to verify the Namespace configuration and correct them if there are any
misconfigured namespaces.
56
57
2. Open Exchange Management Shell
3. Run follow cmdlet to check outlook Anywhere namespace
Get-OutlookAnywhere | Select Server,Internalhostname,Externalhostname |

Fl
58
Note
If upgrading from exchange 2010. Outlook Anywhere must be enabled and
IIS Authentication Must be configured for co-existence, run follow cmdlet to enable
Outlook Anywhere and configure IIS Authentication.
Get-ExchangeServer | Where {($_.AdminDisplayVersion -Like
"Version 14*") -And ($_.ServerRole -Like "*ClientAccess*")} |
Get-ClientAccessServer | Where {$_.OutlookAnywhereEnabled -Eq
$False} | Enable-OutlookAnywhere -ClientAuthenticationMethod
Basic -SSLoffloading $False -ExternalHostName
mail.gooddealmart.ca -IISAuthenticationMethod NTLM,Basic
Run follow cmdlet to configure IIS Authentication if Outlook Anywhere already

enabled.
Get-ExchangeServer | Where {($_.AdminDisplayVersion -Like
"Version 14*") -And ($_.ServerRole -Like "*ClientAccess*")} |
Get-ClientAccessServer | Where {$_.OutlookAnywhereEnabled -Eq
$True} | ForEach {Set-OutlookAnywhere "$_\RPC (Default Web
Site)" -ClientAuthenticationMethod Basic -SSLoffloading $False
-ExternalHostName mail.gooddealmart.ca -
IISAuthenticationMethod Basic}
4. Run follow cmdlet to check OWA Virtual Directory
Get-OWAVirtualDirectory -ADPropertiesOnly | Select

Server,Internalurl,Externalurl | Fl
59
Note
Run follow cmdlet to change settings.
Get-OWAVirtualDirectory -Server GDMEX01 | Set-
OWAVirtualDirectory -ExternalUrl mail.gooddealmart.ca/owa
-InternalUrl mail.gooddealmart.ca/owa
5. Run follow cmdlet to check ECP Virtual Directory
Get-ECPVirtualDirectory -ADPropertiesOnly | Select

60
Note
Get-ECPVirtualDirectory -Server GDMEX01 | Set-
ECPVirtualDirectory -ExternalUrl mail.gooddealmart.ca/ecp
-InternalUrl mail.gooddealmart.ca/ecp
6. Run follow cmdlet to check OAB Virtual Directory
Get-OABVirtualDirectory -ADPropertiesOnly | Select

Note
Get-OABVirtualDirectory -Server GDMEX01 | Set-
OABVirtualDirectory -ExternalUrl mail.gooddealmart.ca/OAB
-InternalUrl mail.gooddealmart.ca/OAB
7. Run follow cmdlet to check WebServices Virtual Directory

61
Get-WebServicesVirtualDirectory -ADPropertiesOnly | Select

Note
Get-WebServicesVirtualDirectory -Server GDMEX01 | Set-
WebServicesVirtualDirectory -ExternalUrl
mail.gooddealmart.ca/EWS/Exchange.asmx -InternalUrl
mail.gooddealmart.ca/EWS/Exchange.asmx
8. Run follow cmdlet to check ActiveSync Virtual Directory
Get-ActiveSyncVirtualDirectory -ADPropertiesOnly | Select

62
Note
Get-ActiveSyncVirtualDirectory -Server GDMEX01 | Set-
ActiveSyncVirtualDirectory -ExternalUrl
mail.gooddealmart.ca/Microsoft-Server-ActiveSync -InternalUrl
mail.gooddealmart.ca/Microsoft-Server-ActiveSync
9. Run follow cmdlet to check ClientAccessServer Virtual Directory
Get-ClientAccessServer | Select Identity,AutodiscoverServiceInternaluri
63
Note
Set-ClientAccessServer -Identity GDMEX01 -
AutodiscoverServiceInternalUri
https://mail.gooddealmart.ca/Autodiscover/Autodiscover.xml
Configuring the Autodiscover Services Connection Point (SCP)

for Exchange 2016 Server
3. Run follow cmdlet to check the existing Autodiscover SCP settings.
Get-ClientAccessService -Identity GDMEX02 | Select

Name,AutodiscoverServiceInternalUri | Fl
4. Run follow cmdlet to update Autidiscover SCP
Set-ClientAccessService -Identity GDMEX02 -AutoDiscoverServiceInternalUri

https://mail.gooddealmart.ca/Autodiscover/Autodiscover.xml
64
Configuring the Client Access Namespaces for Exchange 2016

Server
1. Login Exchange 2016 Server.
3. Run follow cmdlet to change namespaces settings.
$ExternalHostname = “mail.gooddealmart.ca”
$InternalHostname = “mail.gooddealmart.ca”
$Servername = “GDMEX02”
Get-OWAVirtualDirectory -Server $Servername | Set-OWAVirtualDirectory -

ExternalUrl https://$ExternalHostname/owa -InternalUrl
https://$InternalHostname/owa
Get-ECPVirtualDirectory -Server $Servername | Set-ECPVirtualDirectory -

ExternalUrl https://$ExternalHostname/ecp -InternalUrl
https://$InternalHostname/ecp
Get-ActiveSyncVirtualDirectory -Server $Servername | Set-

ActiveSyncVirtualDirectory -ExternalUrl
https://$ExternalHostname/Microsoft-Server-ActiveSync -InternalUrl
https://$InternalHostname/Microsoft-Server-ActiveSync
Get-WebServicesVirtualDirectory -Server $Servername | Set-

WebServicesVirtualDirectory -ExternalUrl
https://$ExternalHostname/EWS/Exchange.asmx -InternalUrl
https://$InternalHostname/EWS/Exchange.asmx
65
Get-OABVirtualDirectory -Server $Servername | Set-OABVirtualDirectory -

ExternalUrl https://$ExternalHostname/OAB -InternalUrl
https://$InternalHostname/OAB
Get-MapiVirtualDirectory -Server $Servername | Set-MapiVirtualDirectory -

ExternalUrl https://$ExternalHostname/mapi -InternalUrl
https://$InternalHostname/Mapi
Get-OutlookAnywhere -Server $Servername | Set-OutlookAnywhere -

ExternalHostname $ExternalHostname -InternalHostname $InternalHostname -
ExternalClientsRequireSsl $true -InternalClientsRequireSsl $true -
DefaultAuthenticationMethod NTLM
Testing the Client Access Namespaces
We can use a host to test with pilot users and make sure there are no issues.
1. Login to a pilot user’s desktop.
2. Open hosts file from c:\Windows\System32\drivers\etc
3. Add mail.gooddealmart.ca map to the IP of exchange 2016 server, save and then close
the hosts file
66
4. Open outlook from the desktop of pilot user and make sure there are no issues.
Cut Over the Client Access namespace to Windows 2016
1. Login to Domain Controller Server and make DNS change for internal clients
2. Open DNS Manager tool
3. Select View and click Advanced
67
4. Change mail.gooddealmart.ca IP address to the same as Exchange 2016 server.
5. Change the TTL from 1 HH to 1 MM and then click OK
6. Change autodiscover.gooddealmart.ca IP address to the same as Exchange 2016 server
7. Change the TTL from 1 HH to 1 MM and then click OK

68
8. Change firewall NAT settings for external clients, make sure change the NAT map form
exchange 2010 to exchange 2016 server
Configuring New Offline Address Book for Exchange 2016 Server
1. Login to Exchange 2016 Server
3. Run follow cmdlet to create a new Offline Address Book and set it as Default
New-OfflineAddressBook -Name “OAB2016” -AddressLists “\Default Global

Address List”
69
4. Run follow cmdlet to check OAB Status
Get-OfflineAddressBook
70
Configuring Receive Connectors for Exchange 2016 server
We need to check the existing Receive Connectors of exchange 2010 server, and then create
them at exchange 2016 server.
1. Login to exchange 2016 server
2. Open Exchange Administrative Center
3. On the Exchange admin center, select mail flow and then click receive connectors.
4. Select Exchange 2016 server from Select server:
71
5. Click + and give the name of the receive connector.
6. Select Frontend Transport Role and select Customize as type and then click Next.
72
7. On the Network adapter binding, keep the default IP ADDRESS and port 25 settings,
click Next.
73
8. On the Remote network settings, click – to remove the default IP ADDRESS and click +
to add IP address that the receive connector will accept mail and then click Finish.
74
9. Double-click the new receive connector, select security.
10. Check the existing receive connector settings and select the same settings at
Authentication and Permission groups and then click Save.
75
11. Repeat steps to create all existing receive connectors.
76
Change Outbound Mail flow Routing (Send Connectors)
We will change the SMTP out bound email flow from the old exchange 2010 server to exchange
2016 server.
1. Login to Exchange 2016 Server.
2. Open Exchange Administrative Center.
3. On the Exchange admin center, select mail flow and then click send connectors.
4. Double-click the existing send connector and select scoping.
77
5. On the Source server: , click – to remove exchange 2010 server and click + to add
exchange 2016 server and then click Save.
78
79
Chapter 5 Connectivity and Mail Flow Test
Chapter 5
Connectivity and Mail Flow

Test
Microsoft Remote Connectivity Analyzer a very good tool to test connectivity and mail flow.
Outlook Connectivity Test
1. Open Microsoft Remote Connectivity Analyzer tool via http://exrca.com.
2. Select Exchange Server and click Outlook Connectivity and then click Next.
3. Fill in all information and click Perform Test.
80
4. Make sure that The Outlook connectivity test completed successfully.
81
82
Note
If Connectivity test failed, you need to Expand All and figure out the error and then fix
it, for this case, it’s Testing HTTP Authentication Method test failed, Run follow cmdlet to
verify and change settings.
Get-OutlookAnywhere | FT Identity,*auth* -AutoSize
Set-OutlookAnywhere -Identity "GDXEX02\rpc (Default Web Site)" -

IISAuthenticationMethods Basic
83
You may need to reboot Exchange servers
Outlook Autodiscover Connectivity Test
1. Open Microsoft Remote Connectivity Analyzer tool via http://exrca.com
2. Select Exchange Server and click Outlook Autodiscover and then click Next.
84
4. Make sure that The Outlook Autodiscover test completed successfully.
85
Exchange ActiveSync Connectivity Test
2. Select Exchange Server and click Exchange ActiveSync and then click Next.
86
4. Make sure that Exchange ActiveSync was tested successfully.
87
Note
If Connectivity test failed, you need to Expand All and figure out the errors and then
fix it, in this case, the error is Exchange ActiveSync returned an HTTP 500 response (Internal
Server Error), Run follow steps to fixed it.
1. Open Active Directory Users and Computers, right-click the test user name
and then select Properties.
88
2. On the Properties page, select Security and then click Advanced.
89
3. On the Advanced Security Settings page, click Enable inheritance and then
click Apply.
90
4. On the Permissions Warning page, click Yes and then click OK.
91
5. Go to Exchange Remote Connectivity Analyzer tool and run test again.
Exchange ActiveSync Autodiscover Connectivity Test
2. Select Exchange Server and click Exchange ActiveSync Autodiscover and then click
Next.
92
4. Make sure that Autodiscover was successfully tested for Exchange ActiveSync.
93
Exchange Web Services Connectivity Test – Synchronization,

Notification, Availability, and Automatic Replies
2. Select Exchange Server and click Synchronization, Notification, Availability, and

Automatic Replies and then click Next.
94
4. Make sure that Tests of all Exchange Web Services tasks completed successfully.
Testing Inbound Mail Flow
2. Select Exchange Server and click Inbound SMTP Email and then click Next.
95
4. Make sure that Inbound SMTP mail flow was verified successfully.
96
5. Make sure the test user received a Microsoft Remote Connectivity Analyzer Test
Message.
6. Open the message in its own window.
7. On the File tab, select Properties.
97
8. Header information appears in the Internet headers box, select and copy all Internet
headers.
10. Select Message Analyzer, paste Internet headers and click Analyze headers.
98
11. Review the Inbound mail flow.
99
Testing Outbound Mail Flow
2. Select Exchange Server and click Outbound SMTP Email and then click Next.
4. Make sure that Outbound SMTP Test was successfully.
100
5. Logon outlook with test user account.
6. Send an email to outside Gmail account.
7. Login Gmail Account and open the email and select Show original.
101
8. Select and copy all Internet headers.
10. Select Message Analyzer, paste Internet headers and click Analyze headers.
102
11. Review the Outbound mail flow.
103
Chapter 6 Post-Configuration Steps
Chapter 6
Post-Configuration Steps
Configuring the Default Mailbox Database for

Exchange Server 2016
1. Logon Exchange 2016 Server, open Exchange Management Shell.
2. Get all mailbox databases information via follow cmdlet.

Get-MailboxDatabase -IncludePreExchange2013
3. Change the Default Mailbox Database name via follow cmdlet.

Set-MailboxDatabase “Mailbox Database 1278187797” -Name DB01-2016
104
4. Run follow cmdlet to check Mailbox Database path.

Get-MailboxDatabase DB01-2016 | Fl *path*
5. Run follow cmdlet to move Mailbox Database to right path.

Move-DatabasePath -Identity DB01-2016 -EdbFilePath E:\DB01-2016\DB01-
2016_DB\DB01-2016.edb -LogFolderPath E:\DB01-2016\DB01-2016_LOGS
105
Create a New Mailbox Database
2. Run follow cmdlet to create a new Mailbox Database.
New-MailboxDatabase -Name DB02-2016 -Server GDMEX02 -EdbFilePath E:\DB02-

2016\DB02-2016_DB\DB02-2016.edb -LogFolderPath E:\DB02-2016\DB02-
2016_LOGS
3. Restart the Microsoft Exchange Information Store Service.
106
4. Run follow cmdlet to mount Mailbox Database.
Mount-Database -Identity DB02-2016
Configuring Mailbox Database Quota
To further verify that you have the same Quota settings for all Mailbox Database.
107
2. Run follow cmdlet to check Mailbox Database Quota settings.
Get-MailboxDatabase -IncludePreExchange2013 | Select

Name,IssueWarningQuota,ProhibitSendQuota,ProhibitSendReceiveQuota
3. Run follow cmdlet to change Mailbox Database Quota settings.
Get-MailboxDatabase -Server GDMEX02 | Set-MailboxDatabase –

IssueWarningQuota 15GB –ProhibitSendQuota 16GB -ProhibitSendReceiveQuota
20GB
Configuring Offline Address Book
2. Run follow cmdlet to check Mailbox Database Offline Address Book settings.
108
Get-MailboxDatabase -IncludePreExchange2013 | Select Name,offline*
Get-OfflineAddressBook
3. Run follow cmdlet to change Mailbox Database Offline Address Book settings.
Get-MailboxDatabase -Server GDMEX02 | Set-MailboxDatabase -

OfflineAddressBook “OAB2016”
Migrate Arbitration Mailboxes

109
2. Run follow cmdlet to check Arbitration Mailboxes.
Get-Mailbox -Arbitration | Select Name,Database
3. Run follow cmdlet to move Arbitration Mailboxes.
Get-Mailbox -Arbitration |New-MoveRequest
4. Run follow cmdlet to check Arbitration Mailboxes move Statistics.
Get-MoveRequest | Get-MoveRequestStatistics
110
111
Chapter 7 Mailbox Migration
Chapter 7
Mailbox Migration
Migrate Pilot mailboxes via Exchange Administrative Center
1. Logon Exchange 2016 Server, open Exchange Administrative Center.
2. On the Exchange admin center page, select recipients.
3. Select Migration, click + sign and select Move to a different database.
112
4. Click Select the users that you want to move and click + sign.
5. On Select Mailbox page, Select Pilot users, click Add, click OK and then click Next.
113
6. On the Move configuration page, enter New migration batch name and select
others required options, click Next.
114
7. On the Start the batch page, select recipients to receive the report after batch
complete, click new.
115
8. Wait until status is completed and the user will receive complete report.
116
117
Chapter 8 Public Folder Migration
Chapter 8
Public Folder Migration
There is no more legacy public folder database, public folder mailboxes also knows as modern
public folders, if you still need public folders, migrate them to Exchange 2016.
Public folder migration is a one-way process, if something goes wrong, you can roll back but any
changes made since the migration will be lost.
1. Login Exchange 2010 Server

2. Download all scripts and supporting files from following link and save to c:\post-
install\pfscripts.
https://www.microsoft.com/en-us/download/details.aspx?id=38407
118
119
3. Open Exchange Management Shell.

4. Run the following command to take a snapshot of the original source public folder
structure.
Get-PublicFolder -Recurse | Export-CliXML C:\Post-

Install\PFMigration\Legacy_PFStructure.xml
5. Run the following command to take a snapshot of public folder statistics such as
item count, size, and owner.
Get-PublicFolderStatistics | Export-CliXML C:\Post-

Install\PFMigration\Legacy_PFStatistics.xml
120
6. Run the following command to take a snapshot of the permissions.
Get-PublicFolder -Recurse | Get-PublicFolderClientPermission | Select-

Object Identity,User -ExpandProperty AccessRights | Export-CliXML
C:\Post-Install\PFMigration\Legacy_PFPerms.xml
121
7. If the name of a public folder contains a backslash \, the public folders will be
created in the parent public folder when migration occurs. Before you migrate,
we recommend that you rename any public folders that have a backslash in the
name. Run the following command to locate public folders that have a backslash
in the name.
Get-PublicFolderStatistics -ResultSize Unlimited | Where {$_.Name -like

"*\*"} | Format-List Name, Identity
122
8. If any public folders are returned, you can rename them by running the following
command.
Set-PublicFolder -Identity <public folder identity> -Name <new public

folder name>
9. To make sure there isn’t a previous record of a successful migration, run following
cmdlet to check the public folder migration status.
Get-OrganizationConfig | Format-List PublicFoldersLockedforMigration,

PublicFolderMigrationComplete
123
10. If the status of the PublicFoldersLockedforMigration or

PublicFolderMigrationComplete properties is $true, run the following command to
set the value to $false.
Set-OrganizationConfig -PublicFoldersLockedforMigration:$false -
PublicFolderMigrationComplete:$false

13. Run the following command to discover any existing serial migration requests.
Get-PublicFolderMigrationRequest | Get-
PublicFolderMigrationRequestStatistics -IncludeReport | Format-List
124
14. Run the following command to removes any existing public folder serial migration
requests.
Get-PublicFolderMigrationRequest | Remove-PublicFolderMigrationRequest
15. Run the following command to discover any existing batch migration requests.
Get-MigrationBatch | where {$_.MigrationType.ToString() -eq

"PublicFolder"}
16. Run the following command to remove any existing batch migration requests.
$batch = Get-MigrationBatch | where {$_.MigrationType.ToString() -eq

"PublicFolder"}
$batch | Remove-MigrationBatch -Confirm:$false
17. Run the following command to make sure no public folder mailboxes exist on the
exchange 2016 server.
Get-Mailbox -PublicFolder
125
18. If the command returned any public folders, run the following command to see if
any public folders exist
Get-PublicFolder
19. If you have any public folders, run the following commands to remove them. Make
sure you've saved any information that was in the public folders.
Get-Mailbox -PublicFolder | Where{$_.IsRootPublicFolderMailbox -eq

$false} | Remove-Mailbox -PublicFolder -Force -Confirm:$false
Get-Mailbox -PublicFolder | Remove-Mailbox -PublicFolder -Force -

Confirm:$false

21. Open Exchange Management Shell as local administrator
22. Run the Export-PublicFolderStatistics.ps1 script to create the folder name-to-
folder size mapping csv file.
.\Export-PublicFolderStatistics.ps1 C:\Post-
Install\PFMigration\PFSizeMap.csv GDMEX01.gooddealmart.ca
126
23. Run the PublicFolderToMailboxMapGenerator.ps1 script to create the public

folder-to-mailbox mapping file. This file is used to calculate the correct number of
public folder mailboxes on the Exchange 2016 Mailbox server.
127
.\PublicFolderToMailboxMapGenerator.ps1 20000000000 C:\Post-

Install\PFMigration\PFSizeMap.csv C:\Post-
Install\PFMigration\PFMailboxMap.csv
128
Note:
Maximum mailbox size in bytes = 20000000000, the value 20000000000 is used to
represent 20 GB
Folder to size map path = C:\Post-Install\PFMigration\PFSizeMap.csv
Folder to mailbox map path = C:\Post-Install\PFMigration\PFMailboxMap.csv
24. Open PFMailboxMap.csv file and change “Mailbox1” to “PFMailbox1” and then
save.
129
25. Copy C:\Post-Install\pfscripts and C:\Post-Install\PFMigration folders from

exchange 2010 server to exchange 2016 server.
27. Copy PFMailboxMap.csv and PFSizeMap.csv files from C:\Post-Install\PFMigration
to C:\Post-Install\pfscripts folder.
29. Run the following command to create the target public folder mailboxes.
.\Create-PublicFolderMailboxesForMigration.ps1 -FolderMappingCsv
PFMailboxMap.csv -EstimatedNumberOfConcurrentUsers:200
Note:
30. Run the following command to create the migration batch.
130
New-MigrationBatch -Name PFMigration -SourcePublicFolderDatabase (Get-

PublicFolderDatabase -Server GDMEX01) -CSVData (Get-Content C:\Post-
Install\PFMigration\PFMailboxMAP.csv -Encoding Byte) -NotificationEmails
csun@gooddealmart.ca
31. Run the following command to start the migration.
Start-MigrationBatch PFMigration
131
32. Open Exchange Admin Center and click recipients and then select migration, you
will see the PFMigration batch status change to Syncing now.
132
33. Once InitialSync is complete, the status will show Synced.
133
34. We are going to lock and complete the public folder for migration
(downtime required)
36. Open Exchange Management Shell as local administrator
37. Run the following command to lock the legacy public folders for
finalization.
Set-OrganizationConfig -PublicFoldersLockedForMigration:$true

39. Open the Exchange Management Shell on your Exchange 2016 server.
40. Run the following command to change the Exchange 2016 deployment
type to Remote.
Set-OrganizationConfig -PublicFoldersEnabled Remote
134
41. Run the following command to complete the public folder migration.
Complete-MigrationBatch PFMigration
42. If the final synchronization is successful, the public folders on the

Exchange 2016 server will be unlocked and the status of the migration
batch will change to Completing, and then Completed.
135
43. Run the following command to assign some test mailboxes to use any
newly migrated public folder mailbox as the default public folder
mailbox.
Set-Mailbox -Identity GDMUSER2 -DefaultPublicFolderMailbox

PFMailbox1
136
44. If everything looks okay, run the following command to unlock the
public folders for all other users.
Get-Mailbox -PublicFolder | Set-Mailbox -PublicFolder -
IsExcludedFromServingHierarchy $false

46. Open Exchange Management Shell as local administrator.
47. Run the following command to indicate that the public folder migration
is complete.
Set-OrganizationConfig -PublicFolderMigrationComplete:$true
137

49. Open the Exchange Management Shell on your Exchange 2016 server.
50. Run the following command on the Exchange 2016 server.
Set-OrganizationConfig -PublicFoldersEnabled Local
51. Run following command on the Exchange 2016 and compare files
contents with previously files and verify success.
Get-PublicFolder -Recurse | Export-CliXML C:\Post-

Install\PFMigration\EX2016_PFStructure.xml
Get-PublicFolderStatistics -ResultSize Unlimited | Export-CliXML

C:\Post-Install\PFMigration\Ex2016_PFStatistics.xml
Get-PublicFolder -Recurse | Get-PublicFolderClientPermission |

Select-Object Identity,User -ExpandProperty AccessRights | Export-
CliXML C:\Post-Install\PFMigration\Ex2016_PFPerms.xml
Well that wraps up this amazing book on Exchange 2010 to Exchange 2016 migration. Stay
tuned as in our next book we will Migrate this Exchange 2016 environment to Office 365.
138
139
Contact Us Join us at MVPDays and meet great MVP’s like this in person
Contact Us
Join us at MVPDays and meet

great MVP’s like this in
person
If you liked their book, you will love to hear them in person.
Live Presentations
Dave frequently speaks at Microsoft conferences around North America, such as TechEd,
VeeamOn, TechDays, and MVPDays Community Roadshow.
Cristal runs the MVPDays Community Roadshow.
You can find additional information on the following blog:
www.checkyourlogs.net
www.mvpdays.com
Video Training
For video-based training, see the following site:
www.mvpdays.com
140
Live Instructor-led Classes

Dave has been a Microsoft Certified Trainer (MCT) for more than 15 years and presents
scheduled instructor-led classes in the US and Canada. For current dates and locations, see the
following sites:
 www.truesec.com
 www.checkyourlogs.net
Consulting Services
Dave and Cristal have worked with some of the largest companies in the world and have a
wealth of experience and expertise. Customer engagements are typically between two weeks
and six months.
141
Twitter
Dave, Cristal, Émile, and Cary on Twitter tweet on the following aliases:
 Dave Kawula: @DaveKawula
 Cristal Kawula: @SuperCristal1
 Émile Cabot: @Ecabot
 Cary Sun: @SifuSun
142

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Migrating from Exchange

2010 to 2016 – Step by Step

Dave Kawula - MVP

Copyright © 2018 by MVPDays Publishing

Warning and Disclaimer

About the Authors

Cary Sun – CCIE #4531

Emile Cabot - MVP

About the Authors ......................................................................................................... v

Cary Sun – CCIE #4531 ................................................................................................ vi

North American MVPDays Community Roadshow ................................................... 14

Exchange 2016 Design Guidance............................................................................... 17

.NET Framework .................................................................................................. 21

Exchange 2016 Prerequisites ..................................................................................... 23

Deploy Exchange Server 2016 Mailbox Role Server ................................................. 36

Configure Exchange Server 2016 ............................................................................... 56

Connectivity and Mail Flow Test ................................................................................ 80

Outlook Connectivity Test..................................................................................... 80

Chapter 6.................................................................................................................... 104

Post-Configuration Steps ......................................................................................... 104

Chapter 7.................................................................................................................... 112

Mailbox Migration ...................................................................................................... 112

Chapter 8.................................................................................................................... 118

Public Folder Migration ............................................................................................. 118

Contact Us ................................................................................................................. 140

Live Instructor-led Classes ...................................................................................... 141

North American MVPDays

We often get asked the question “Who should attend MVPDays”?

Exchange 2016 Design

Current State Feature State

Internal corporate network

Internal corporate network

Exchange Exchange Exchange

Active On-premises Active Directory

Exchange 2016 System requirements

Coexistence of Exchange 2016 with earlier versions of Exchange

Exchange version Exchange organization coexistence

Exchange 2007 and earlier versions Not supported

Exchange 2013 Supported with Exchange 2013 Cumulative Update 10 or

 Update Rollup 11 Exchange 2010 SP3 or later on

Network and directory server requirements for Exchange 2016

 Windows Server 2016 Standard or Datacenter

 Windows Server 2012 R2 Standard or Datacenter

 Windows Server 2012 Standard or Datacenter

 Windows Server 2008 R2 Standard or Enterprise

 Windows Server 2008 R2 Datacenter RTM or later

 Windows Server 2008 Standard, Enterprise, or

Supported operating systems for Exchange 2016

 Windows Server 2012 R2 Standard or Datacenter

 Windows Server 2012 Standard or Datacenter

Management tools  Windows Server 2016 Standard or Datacenter*

 Windows Server 2012 R2 Standard or Datacenter

 Windows Server 2012 Standard or Datacenter

 64-bit edition of Windows 10

 64-bit edition of Windows 8.1

Exchange 2016 CU5 V Not supported Not supported

Exchange 2016 CU4 V V V

(Starting with (Starting with

Exchange 2016 CU3 V V V

Exchange 2016 CU2 Not supported V V

(If you're upgrading to

Exchange 2016 RTM Not supported Not supported V

Exchange 2016 Prerequisites