Part 2 of this Screencast is available here.

In this two-part screencast we demonstrate how to upgrade from Exchange 2013 to Exchange 2019. As usual, we follow our step-by-step approach; each step encompasses a set of logically related tasks. In addition, our demonstration is focused on the practical side of the upgrade and outlines some of the most common problems that you might hit on the field.

While most guides and instructions on the web use the so called textbook style – they assume that you have a perfectly configured network, and healthy Active Directory and Exchange Organization – in part one, we start with the obligatory health checks and reports that are always required when you introduce or upgrade applications that bring schema changes and rely heavily on Active Directory.

As you will see, many of the tasks and prerequisite checks are performed in PowerShell and command line. For your convenience, we have published the text file with our project plan and the commands that we are using in the Screencast here .

Step 1 We start with an overview of our existing configuration and discuss the plan that we will be following.

Step 2 Next, we discuss the Active Directory requirements and confirm that we are covering them. Then we run an Active Directory Health Check, test the AD replication, check the DNS health and create a DNS report with DNSLint.

Step 3 We cover a lot of ground in this step. We start with checking the Exchange 2013 prerequisites and the Exchange Organization health. As you will see in this video, the Exchange HealthChecker.ps1 PowerShell script is extremely helpful in diagnosing issues that need to be fixed before we move further. Making sure that all mailboxes have a default OAB assigned is quite often missed and should be done as well. We document the existing configuration – mailbox storage quotas, namespaces, email routing topology, any custom connectors, and export the trusted Exchange SSL certificate.

Step 4 In this step, we configure the new server for Exchange 2019 and prepare Active Directory and Domains. It is a good idea to extend the AD schema and prepare the AD domains in advance so you can catch earlier any underlying issues and resolve them before the actual Exchange 2019 installation. In addition, we configure dedicated volumes for the Exchange Databases and Log files using ReFS with the integrity streams feature disabled as recommended by Microsoft. Finally, we install the Exchange 2019 prerequisites.

Step 5 This is where we perform the actual Exchange 2019 installation. Keeping an eye on the tasks that are happening in the background can turn out to be extremely helpful in case you hit any issues, and we show you how to start monitoring in real time the ExchangeSetup.log before you launch the Exchange Installation Wizard. When the installation completes, we pay special attention to the problem introduced with the additional Service Connection Point (SCP) that is added automatically to Active Directory during the Exchange 2019 installation, and that needs to be addressed ASAP.

Step 6 In this step, we start with a validation of the Exchange 2019 installation. Then we move to the SCP issue – since Exchange 2019 uses a self-signed certificate, the Outlook clients that get the new SCP when querying Active Directory will get a certificate popup warning. To resolve the issue, we configure the Exchange 2019 internal and external virtual directories and the SCP based on the virtual directories namespaces that we have documented earlier in step 3. At the end, we import the Exchange trusted certificate to Exchange 2019.

Step 7 In the last step, we run again the Exchange HealthChecker.ps1 on the newly installed Exchange 2019 to detect and resolve any problems with the server and its configuration. In addition, we make sure that Exchange 2019 is fully updated and all Security Updates are installed.