Migrating to Office 365 - Step by Step
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Migrating to Office 365 - Step by Step

Volume 1

About the Book

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 bring you real world step-by-step guidance from our expert MVP Authors on Migrating to Office 365 from an on premises Exchange environment. It has been written with the most current techniques possible to help with your migrations and learning process.    

About the Authors

Dave Kawula
Dave Kawula

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

Dave Kawula

Episode 87

Cary Sun
Cary Sun

Cary Sun is an Principal Consultant, He has a strong background specializing in datacenter and deployment solutions, and has spent many years performing infrastructure analyses and solution implementations for organizations ranging from 20 to over 600,00 employees. He hold CISCO CERTIFIED INTERNETWORK EXPERT (CCIE No.4531) from 1999 , Cisco Champion 2018-2019 and Microsoft Most Valuable Professional (MVP). Cary is a published author with serveral titles, include blogs on Checkyourlogs.net, technical editors/reviewer for many books, including Master Storage Space Direct Volume 1.

BLOG: www.checkyourlogs.net

Personal Website: carysun.com

Twitter: @SifuSun


Specialties: CCIE /CCNA / MCSE / MCITP / MCTS / MCSA / Solution Expert / CCA

Table of Contents

Acknowledgements iv

From Dave iv

About the Authors v

Dave Kawula - MVP v

Cristal Kawula – MVP vi

Cary Sun – CCIE #4531 (Cisco Champion) vii

Contents ix

Introduction 13

North American MVPDays Community Roadshow 13

Sample Files 14

Additional Resources 14

Chapter 1 16

Environment Overview 16

Exchange Migration to Office 365 16

Prerequisites 17

On-premises Exchange organization 17

On-premises Exchange releases 18

On-premises server roles 18

Office 365 19

Custom domains 19

Active Directory synchronization 19

Autodiscover DNS records 19

Office 365 organization in the Exchange admin center (EAC) 19

Certificates (If Active Directory Federation Services is being deployed) 20

Hybrid deployment protocols, ports, and endpoints 20

On-premises Active Directory 22

Hybrid Identity Required Ports and Protocols 23

Chapter 2 24

Configure Azure AD (Office365) 24

Add and verify the on-premise domain in Azure AD (Office 365) 24

Chapter 3 31

Configuring Hybrid Identity with Office 365 31

Add and verify the on-premise domain in Azure AD (Office 365) 31

Deployment Certificate (If Active Directory Federation Services is being deployed) 38

Configure UPN suffix 41

Enable Active Directory Recycle Bin 42

Deployment Azure AD Connect 43

Prerequisites 44

Install Azure AD Connect with Express settings 45

Install Azure AD Connect with Customized settings 55

Enable Password Change for ADFS 90

Deploy Active Directory Federation Service (ADFS) 94

Install Active Directory Federation Services Server (if you Install Azure AD Connect with Customized settings, this was being installed) 95

Install the AD FS server role via Windows PowerShell 96

Configure External DNS A Record for ADFS 96

Configure Internal DNS for ADFS 96

Configure the first federation server in a new federation server farm (if you Install Azure AD Connect with Customized settings, this was being configured) 98

Verify Active Directory Federated Services (ADFS) 104

Federate your Domain with office 365 105

Chapter 4 110

Configure Hybrid Services between on-premises Exchange 2016 (2013/2010) with Office 365 110

Install and Run Hybrid Configuration wizard with Hybrid Configuration (without ADFS) 111

Install and Run Hybrid Configuration wizard with Minimal Hybrid Configuration (with ADFS) 130

Install and Run Hybrid Configuration wizard with Full Hybrid Configuration (with ADFS) 140

Verify Hybrid Configuration 157

Add Office 365 Forest to Exchange Management Console 161

Set up connectors to route mail between Office 365 and on-premises exchange Server 163

Create a connector from Office 365 to on-premises email server (It will be added automatically if you were using Full Hybrid configuration) 163

Create a connector from on-premises email server to Office 365 (It will be added automatically if you were using Full Hybrid configuration) 177

Configure on-premises email server send connector to Office 365 (It will be added automatically if you were using Full Hybrid configuration) 182

Configure on-premises email server Receive Connector to relay email 187

Change MX record to redirect mail flow from the Internet to Office 365 194

Migration Mailboxes between on-premises exchange server with Office 365 195

Review and Enable the MRSProxy service 195

Create a migration endpoint 196

Move on-premises mailboxes to Exchange Online 203

Move Exchange Online mailboxes to the on-premises organization 210

Chapter5 216

Meet great MVP’s like this in person 216

Live Presentations 216

Video Training 216

Live Instructor-led Classes 216

Consulting Services 217

Twitter 218

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