As you may know, SharePoint Server 2019 is now out of preview. Its general availability was announced on October 22, 2018.

With this recent announcement, two questions at the top of the minds of many SharePoint Server admins are:

1. How do we get to SharePoint 2019 from our current SharePoint Server version?
2. And what will the upgrade process be like?

The answer to both questions is, “It depends on your current SharePoint version and the upgrade option that you choose”.

This article will dig deep into the available upgrade options starting from MOSS 2007 (WSS 3.0) all the way up to SharePoint Server 2019.

In the process, I will provide insights on upgrade versus migration and information that will help you in selecting the best upgrade option for your company.

Related Reading: Setting up a SharePoint 2016 dev farm in Azure

Available Upgrade Options To SharePoint 2019

Usually, Microsoft provides a native upgrade option with new SharePoint Server versions. SharePoint Server 2019 is no exception. But the native upgrade option is certainly not the only option and many times, it may not even be the best option.

To clarify, let us first review three common SharePoint upgrade situations:

1. Native SharePoint Upgrade

Microsoft’s official native SharePoint upgrade works via a “database attach” process. So, if you were upgrading from SharePoint 2016 to SharePoint 2019, this would involve “detaching” your existing content databases from SharePoint 2016 and “attaching” them to SharePoint 2019. During the attach process, the content databases will be upgraded after which they will be made available in SharePoint 2019.

I used the above example of upgrading from SharePoint 2016 to SharePoint 2019 for good reason – the native upgrade option only supports upgrading from one version of SharePoint Server to the next immediate higher version. It does not allow you to skip versions.

So, using the native upgrade option, you can upgrade from SharePoint 2013 to 2016 or from SharePoint 2016 to 2019. It does not allow directly upgrading from SharePoint 2013 to 2019.

More on this below.

Specific To SharePoint 2013: You may also want to note that if you want to upgrade a SharePoint 2013 environment (to 2016) using the native upgrade method, any web applications that are in windows authentication mode must first be converted to to claims authentication because claims authentication is the default mode in SharePoint 2016 and SharePoint 2019.
 
In addition, all SharePoint 2013 site collections must be upgraded from compatibility level 14 to compatibility level 15. This can be done using the Upgrade-SPSite cmdlet. This will ensure that the database versions are upgraded to 15.0.4481.1005 or higher (required for SharePoint 2016 and above).

You may notice from the above that if the version of SharePoint you want to upgrade to 2019 is NOT SharePoint 2016, multiple sequential upgrades will be required.

Here’s how the native upgrade path will look like starting from MOSS 2007 (WSS 3.0):

Steps	Source	Target	Upgrade Options
Step 1	MOSS 2007 (WSS 3.0)	SharePoint 2010	In-place upgrade, Database attach upgrade, Hybrid upgrade
Step 2	SharePoint 2010	SharePoint 2013	Database attach upgrade only
Step 3	SharePoint 2013	SharePoint 2016	Database attach upgrade only
Step 4	SharePoint 2016	SharePoint 2019	Database attach upgrade only

From the above table, if you want to upgrade SharePoint 2010 to SharePoint 2019 using the native upgrade method, you will have to do this: SharePoint 2010 >> SharePoint 2013 >> SharePoint 2016 >> SharePoint 2019.

IMPORTANT: When you do a native (database attach) upgrade, only your content databases get upgraded. This is known as a content-only upgrade. Your configuration does not get upgraded. This means that, while your documents, libraries, lists, pages, and site structure will be upgraded, aspects of your customizations will not be upgraded and stuff like your custom code, WSPs, workflows, custom WebParts, etc. will not be upgraded either. They will need to be rebuilt, redeployed, and/or reconfigured (as the case may be) in your new SharePoint version.

2. Selective/Parallel SharePoint Upgrade (Or Migration)

This selective or parallel SharePoint upgrade option is not really an upgrade method, technically speaking. It is a migration.

This option involves creating a whole new SharePoint 2019 environment that runs in parallel with your existing (older) SharePoint environment. Then you just selectively migrate the content, features, custom solutions, and configurations that you want to keep on SharePoint 2019.

In most cases, this is usually the preferred upgrade method. It is certainly the upgrade approach I’d generally recommend for most organizations that already have full-blown SharePoint Server installations. It offers several advantages over the native upgrade technique.

Some of these advantages include:

• It allows you to selectively migrate only the content you want to keep and shed the stuff that your organization no longer wants (or stuff that are not supported anymore). The native upgrade method doesn’t let you do this.
   
• Another major advantage of this parallel upgrade path is that it is the only upgrade path that lets you directly migrate to SharePoint 2019 from versions of SharePoint that are NOT SharePoint 2016.
   
  With this parallel upgrade method, you can skip a version or even skip multiple versions. For example, if you have SharePoint 2010 and want to move straight to SharePoint 2019, no problem. Just install a fresh copy of SharePoint 2019 in parallel and then gradually migrate your content and configuration over. Easy.
   
  No headaches about first upgrading to SharePoint 2013, figuring out bugs and incompatibilities, worrying about database and site collection compatibility levels, upgrading again to SharePoint 2016, fixing bugs again, and then finally upgrading to SharePoint 2019.
   
• This parallel upgrade path also allows for great flexibility during your migration. You can make changes to your content and structure during the migration process itself. You can even update workflows in the process if you like. This is as opposed to the big bang approach of the native upgrade technique where everything must happen in one shot.

3. Upgrading To Office 365

This approach is quite different from the others because it involves upgrading straight to the cloud. So, instead of on-premise SharePoint 2019, we just upgrade our old on-premise SharePoint implementation to Office 365.

The latest on-premise versions of SharePoint are actually quite similar to Office 365 from a look-and-feel and features perspective. And considering the cloud-first approach that most organizations are taking these days, it makes sense to consider Office 365 as an upgrade option.

One key advantage of Office 365 is that since it generally receives features first (before on-premise), it allows companies to always have all the best stuff that SharePoint provides without ever needing to worry about versions and upgrades and all that stuff.

Choosing An Upgrade Path

In order to decide on the best SharePoint upgrade path for your organization, you may want to consider the following questions:

1. Do You Already Have Everything You Need In Your Existing SharePoint Version?

If you love technology like I do, you could easily get carried away with excitement over fancy new tech and may lose sight of the actual benefits the new tech provides. Since businesses run to make money, it is important to carefully consider the business reasons for a SharePoint upgrade and whether the potential benefits of the new SharePoint version are enough to justify the cost of upgrading.

So, if your existing version of SharePoint continues to meet your requirements and helps you solve your major business challenges and if it is a version that is still well supported by Microsoft, then it may be a good idea to stay with the old SharePoint version for now and defer upgrading to a later date.

But if you are still on very old versions like SharePoint 2010 or MOSS 2007 or even SharePoint 2003, then you should seriously consider upgrading very soon. SharePoint upgrades or migrations require a good amount of time, especially if you have a big implementation (lots of users, documents, workflows, etc). So, the earlier you start moving away from unsupported versions, the better.

As previously mentioned, the native upgrade method from SharePoint 2010 or MOSS 2007 will require a number of sequential upgrades. So, if you’re on any of those older versions, I strongly recommend the selective/parallel migration approach instead.

Unless you’re already on SharePoint 2016, I think the parallel migration path should be the primary upgrade path to consider.

2. Do You Have A Simple Or Complex SharePoint Environment?

If your organization has a complex SharePoint environment, the big bang approach of the native upgrade technique via database detach and attach is almost a no go. The number of things that could break if you use the native upgrade method on a complex environment are just too many. And the time spent hunting down and fixing issues could easily end up being more than the time that would have been required to do a low-impact parallel migration.

There is also the issue of how to deal with downtime during a big bang upgrade. In my experience, it could get messy really quick.

Besides the associated risks of the native upgrade option (as compared with the parallel upgrade option), companies with complex SharePoint environments might also want to make changes to their SharePoint content and configuration on the way to SharePoint 2019. This is just not possible with the native upgrade option.

If however, your SharePoint environment is small and relatively simple (no much customizations, OOTB functionality for the most part), you may want to consider the native upgrade method as it may be much quicker in your case. This is even more so if you’re already on SharePoint 2016 and only need one upgrade step to get to the latest SharePoint version.

3. Will You Be Migrating Everything?

If your current SharePoint environment has been running for a while, you will have quite a lot of data. Probably more than you realize. Unless your organization has excellent information management practices (which is hardly ever the case).

There will be lots of documents (and probably multiple versions of those documents if versioning is turned on), lots of users, lots of workflows, and lots of custom configurations. Much of this data may no longer be needed and the SharePoint version upgrade is a great opportunity to perform some “spring cleaning” and eliminate all content and configuration that you no longer need. The parallel/selective upgrade method is the best way to do this.

4. Is Office 365 Even An Option For Your Organization?

Not all organizations are ready to move their SharePoint implementations to the cloud. However, many organizations do have data subsets and workloads that are well suited to the cloud and may benefit from a hybrid (on-premise AND Office 365) SharePoint approach. Another option could even be “on-premise” SharePoint hosted on Azure Servers.

If on the other hand, your organization is fast embracing cloud technologies, then Office 365 is an option you may want to strongly consider.

5. Are Regulatory And Legal Requirements Becoming A Concern?

Many companies are good at accumulating data but very poor at data governance and information management. If this is becoming a problem in your current SharePoint environment, the upgrade to SharePoint 2019 provides a great opportunity to review everything, make appropriate changes, and put in place proper data governance and information management procedures.

The parallel/selective upgrade technique is best for this scenario because of the flexibility is provides.

Conclusion

As quite clearly expressed in this article, if you are remaining on-premise, I have a strong bias and highly recommend the parallel/selective upgrade path. This position is shared by many other SharePoint experts in the industry and the justification for it has been explained above.

Upgrading SharePoint is a great opportunity to not just have a shiny new SharePoint environment but to actually “upgrade” your processes and how SharePoint is used across the board. The analysis required during a SharePoint upgrade can easily be extended to kill multiple birds with a single stone.

In the end, no matter the upgrade path you choose, native, parallel, or Office 365, the ultimate goal usually remains to get the most value out of SharePoint for our businesses and our users.

I hope the insights I shared in this article will help simplify your decision making process.