Evaluate Weigh the pros and cons of technologies, products and projects you are considering.

Microsoft subscriptions aren't right for everyone

With the push to deliver Office and Windows as services, Microsoft subscriptions will be a reality in most IT departments one way or another. But not all organizations are good candidates for going all-in.

Microsoft will continually update Windows 10 rather than release another version going forward, and earlier this month, the company announced that Office 2019 would only be available on Windows 10. That means organizations must either adopt the new Windows as a service model if they want to stay with on-premises Office, or shell out for the cloud-based Office 365 if they stay on earlier OSes. And without confirmation of another version of Office after 2019, Office 365 could be the only way for companies to go in the future.

“It’s a phenomenon that’s been a long time coming,” said Jon Hassell, a freelance technical writer and consultant in Charlotte, N.C. “This seems to be the first announcement that really tightens the noose around people who want to opt out of the subscription model.”

Businesses that don’t have a lot of IT staff might be better off with Microsoft subscriptions for Office 365 and Windows as a service, as well as people that work for themselves, because cloud helps offload management from IT, Hassell said. But application deployment isn’t a one-size-fits-all scenario, so it might not make sense for all organizations to be cloud-only.

Larger organizations that support a lot of different business applications, for example, could run into problems with apps that integrate with Microsoft but might not update at the same cadence as Microsoft’s products. It’s largely on the third-party software providers — take SAP, for instance — to make sure their applications update in tandem so the integrations continue to work properly.

But it’s far-fetched to imagine that all vendors that integrate with Windows or Office 365 could promise to update their applications at the same cadence as Microsoft. Even now, Microsoft could be a little bit better about testing compatibility to make sure organizations’ other apps will work with their existing integrations after Microsoft updates, Hassell said.

For that, the onus tends to be on IT departments themselves. If the continual automatic Windows 10 updates are any indication, it’s going to be tricky for organizations to keep pace with the incompatibilities and other issues that arise post-update.

“Synchronizing all of that stuff is a full time job already, so when you move the goal post all the time … it gets more complicated,” Hassell said.

One example of recent issues with updates is the Windows patches that Microsoft released in January for the Meltdown and Spectre vulnerabilities. Organizations saw a variety of problems result from the patches. Some IT pros, facing a strong sense of urgency from Microsoft because of the vulnerabilities’ high security risks, regretted patching their software quickly without testing everything first.

“There’s this mentality within Microsoft that it’s better to just move fast and break things,” Hassell said.

Now IT pros must determine whether to accept this new-world model of Microsoft subscriptions and go all-in on Windows as a service and Office 365 in the coming years.

“We see the direction Microsoft is going in more clearly now,” Hassell said. “It’s decision time for companies.”