Trials of a Network Admin

Office 2019 recently released and accordingly, you may be looking into the upgrade process and any challenges it may bring. We recently found ourselves in this situation and the upgrade is, unfortunately, anything but simple. My usual disclaimer applies: some of the information below is a result solely of my own experiences in trying to upgrade our organization. If there are any errors, please comment and let me know.

MSI vs. Click-To-Run

Prior versions of the Office Suite used the well-known MSI format. MSI allows the use of Group Policy for network installs, and most large organizations have plenty of experience with the format. So of course Microsoft had to fix something that wasn’t broken.

Office Pro Plus 365 and Office 2019 (I’ll cover the differences in a moment) use Click-To-Run technology (CTR) which Microsoft touts as a “modern” deployment method.

Here’s a quick comparison of the two methods:

MSI

• Deployed via Group Policy
• Installs from local media
• Patches directly from Windows Update or through WSUS

CTR

• Deployed via the Office Deployment Tool
• Installs from local media or directly from the Internet
• Patches directly from the Internet or from a network share (not through WSUS)

There are plusses and minuses to both methods, but CTR is seemingly the future so we have no choice but to deal with it.

Product Channels

For all practical purposes, there are five variants of the current Office Suite, each of which is considered a “channel.”

• Office 365 Pro Plus Semi-Annual
• Office 365 Pro Plus Semi-Annual (Targeted)
• Office 365 Pro Plus Monthly
• Office 365 Pro Plus Monthly (Targeted)
• Office 2019

The 365 SKUs are retail, and their license is tied to an appropriate Office 365 subscription that includes the Office Suite. You can choose to get either monthly or semi-annual feature updates, while security patches are applied regularly regardless. The “targeted” channels are essentially “sneak-peeks” of upcoming changes.

Where it gets confusing is that Office 2019 is essentially nothing more than a point-in-time snapshot of Office 365 Pro Plus, that will not get any feature updates; it will receive security updates only. This version is also the only one that can be volume-licensed using KMS.

As of November 1st, the most recent O365 Pro Plus Semi-Annual channel is version 1803, Office 2019 is considered version 1808, while the O365 Pro Plus Monthly channel is 1809, and the monthly targeted channel is 1810. Each has different feature sets. See Microsoft’s update history for O365 Pro Plus for more info.

Licensing

As mentioned, any of the Pro Plus channels imply retail licensing, and they must be activated against an Office 365 account that is entitled to the appropriate applications. This is fairly straightforward in an office setting where people don’t switch computers too often, but it poses a challenge in a school or other shared computer setting. In this case, you want to use shared computer licensing, and ideally license token roaming as well.

Office 2019 implies volume licensing, either using MAK or KMS. In this sense it’s identical to prior volume-licensed versions of the Office Suite. Note your KMS server will need an update to activate Office 2019.

Installation

Whether you want to install Pro Plus or 2019, and regardless of the desired channel, you will need to use the Office Deployment Tool (ODT). Essentially you will need to create an XML file that defines various options, including the desired channel, the installation source, and the update method. Microsoft’s documentation is actually pretty thorough, so you shouldn’t run into too many problems. There are a few caveats though:

• The setup.exe that you run to install the suite is actually just a stub installer. In some cases (and I haven’t yet figured out the specifics), setup.exe will terminate successfully before the apps are installed. There is a further installer that will continue to run in the background.
• The XML file gives you an option to remove any MSI-installed versions found. In my testing, this setting is ignored and the installer will always remove any older versions of Office. Even better, it will remove applications like Visio or Project that aren’t part of the suite and are thus not going to get reinstalled.
  
• Normally, the suite is going to be configured to take updates directly from Microsoft. You can no longer use WSUS to patch Office. You can technically control patches by disabling updates from the Internet and then manually downloading them to a network share, but that’s likely impractical. Realistically administrators have no choice but to accept giving up control of Office patches if they want to stay reasonably current. As an example of how little control we now have over the patch process, I left Word open with this document being edited on Friday, running version 1809. I came in Monday morning to the document still open, with Word running version 1810.

Co-Existence With Visio or Project

While neither Visio nor Project are included in the O365 Pro Plus suite, or in Office 2019, they are considered part of Office and the ODT is used to install them as well. This has implications for installing either application alongside the Office Suite. Microsoft has a KB article about that here, but it’s missing one critical bit of info.

According to Microsoft, it is possible to install Office 365 Pro Plus with a retail (subscription-based) license alongside Project 2019 or Visio 2019 using a volume license. However in the “additional information” section of the linked article, Microsoft adds a major restriction: all installed Office applications must be using the same update channel.

The reality is that restriction precludes using O365 Pro Plus along with volume-licensed copies of Project or Visio, because the retail versions use one set of update channels, and the volume license versions use a different one. Perhaps I’m missing something here but I could not get retail O365 Pro Plus to work properly alongside volume licensed (either MAK or KMS) versions of Project or Visio.

If a volume-licensed edition of Project 2019 or Visio 2019 is already installed, the O365 Pro Plus install may succeed (it did for me), however none of the applications will activate. The volume-license apps generate an error that the license has changed, and the retail apps simply refuse to license with a generic error.

If O365 Pro Plus is installed first, the volume license versions will refuse to install due to the unavoidable channel mismatch.

If you install the retail versions of Project or Visio alongside O365 Pro Plus, you cannot activate them using KMS or MAK because only the volume license version supports volume activation.

So the long and short of it is that if you need either Project or Visio, you either have to use Office 2019 and the volume license edition of Project or Visio, or you need an O365 subscription that includes rights to all applicable products.

In Conclusion

Anytime a long-standing technology changes, there are growing pains. We’re still too new to using CTR to see any clear advantages, but the move itself isn’t all that painful. However, the changes to how applications are updated, licensing, and the restrictions on product coexistence all have significant implications to cost, both in dollars and labor.

Most corporations will probably be content to stay with the volume-license editions of Office, but in education, Microsoft continues to add – and quickly publicize – new features that are only available in the monthly retail channel. So while we have the option of staying volume-licensed, the reality is we would be doing our students a disservice by not offering the latest features. And that means dealing with all the accompanying quirks.