Plan to Migrate to an Exchange 2019 Server

In this article, we will look at the option of upgrading to the latest Exchange Server 2019. As it is difficult to showcase every possible method or checklist in a single article, we will explore the most common setups, along with comparisons, tips and other factors to consider. You would have the following scenarios:

- New server implementation

- Upgrading from Exchange 2010, 2013 or 2016

Let’s take a look at the checklist that you may need before embarking on the installation or migration to Exchange Server 2019.

1. Exchange Server Edition and Licensing

If you are going for standalone version, the Exchange Server 2019 — Standard is enough. If you are planning to have not more than 5 mailbox databases, you can remain with it. This doesn’t mean that you cannot have more than 5 mailbox databases, but you can only mount 5 concurrent databases. If you are planning to split databases and have more than 5 mailbox databases mounted, then you would need to go for the Enterprise edition.

With regards to server licenses, if you are going to set up a Database Availability Group (DAG) for high availability of Exchange, you would need an Exchange Server 2019 Standard or Enterprise for every server in your DAG.

With regards to usage by the users, if you are upgrading from an existing Exchange Server, you need to re-purchase the user client access licenses (CALs) for all the users, which will be accessing the server.

The purchase of CALs is a one-time cost and will not have an impact on server cost as nothing extra is needed to be installed. If you have a DAG, you need to purchase user CALs for only the number of users and not for other members.

So, if you have a DAG with 2 member servers and a total of 30 users, you need to purchase:

- X2 Microsoft Exchange Server 2019 Enterprise

- X30 Microsoft Exchange Server 2019 User CALs

2. Operating System

For installing Exchange Server 2019, you must have Windows Server 2019. You cannot install Exchange Server 2019 on another operating system. So, you would need to consider the purchase of Windows Server 2019 Standard in your budget.

If you are installing Windows Server 2019 in a virtual environment with only one Exchange Server 2019 installation, you will not have any problems as you can install two virtual servers with one license. This will allow you to install one Active Directory server and the other to be used for the Exchange Server.

3. Active Directory

One important thing to take into consideration is the compatibility of Exchange Server 2019 with the Active Directory forest and domain level. If you have an infrastructure running with Windows Server 2008 R2 or Windows Server 2012 forest/domain levels, you need to consider the upgrade as these operating systems are out of support. You cannot have an Exchange Server 2019, if the forest level is not set at Windows Server 2012 R2 or higher.

With regards to the operating system of your Active Directory servers, you can run the following operating systems:

- Windows Server 2019 Standard or Datacenter

- Windows Server 2016 Standard or Datacenter

- Windows Server 2012 R2 Standard or Datacenter

4. Co-Existence

This part will only be useful if you are going to upgrade from older version of Exchange Server to Exchange Server 2019. It is to be noted that only Exchange Server 2013 or 2016 can co-exist with the Exchange Server 2019.

If you still have Exchange Server 2010, you will not be able to install Exchange Server 2019 alongside of it and move the mailboxes from one to another. You will need to hop migrate to either Exchange 2013 or 2016 before moving to Exchange Server 2019. So, in this case, follow the below given steps to migrate from Exchange 2010 to 2019.

- Install Exchange 2013 or Exchange 2016

- Move all mailboxes to the newly installed server

- Decommission Exchange 2010

- Upgrade the Active Directory servers (if needed)

- Make sure to have the forest/domain level on Windows Server 2012 R2 or higher

- Install Exchange Server 2019

- Move all mailboxes to the newly installed server

- Decommission Exchange Server 2013 or 2019

5. Unified Communications Integration

With Exchange 2019, your Lync 2013 must be updated to Cumulative Update 10 (CU 10). If you are running Skype for Business server, Cumulative Update 7 (CU 7) or later must be installed. Older versions or versions which are not in line with the above will not be compatible. Now, if you are using the Lync server attached with your telephone system and want to continue using mailbox facility, think again if you are installing Exchange Server 2019. If you decide to upgrade to Exchange Server 2019, you would need to find another solution as Unified Messaging in Exchange Server 2019 has been removed and third-party application must be used.

6. User Software

Office applications form an essential part when installing and upgrading to Exchange Server 2019. This is because if you have an old version of Outlook, users will not be able to connect to their respective mailboxes. Only the following Office versions are compatible with Exchange Server 2019.

- Microsoft 365 Apps for enterprise

- Outlook 2019

- Outlook 2016*

- Outlook 2013*

- Outlook for Mac for Office 365

- Outlook 2016 for Mac

* Only compatible with Windows 7 if the KB3140245 is applied to allow TLS 1.1 and 1.2, otherwise it will not work.

Since Windows 7 has reached its end-of-life, it is highly recommended for safety and compatibility to have all the user machines running with the latest Windows 10. Windows 7 can still work with Exchange 2019, if you have the necessary patching to allow the new cryptographies.

Wrapping Up

In this article, we have discussed some important considerations that you need to go through before migrating to Exchange Server 2019. These include Exchange Server Edition and Licensing, Operating System, Active Directory, Co-Existence, Unified Communications Integration, and User Software. But we forgot to consider the fact that “what if the upgrade or migration goes wrong”. Well, in this case, you need to have in hand Stellar Converter for EDB, which is an essential tool for every Exchange Admin and assists in exports and migrations. With Stellar Converter for EDB, you can easily attach an EDB database of any version, export it to PST and other formats, and can also migrate mailboxes, public folders directly to a live Exchange or Office 365 tenant.