Microsoft wants to make life easier for enterprise customers. Starting today, it is committing to fix any custom applications that may break as a result of updates to Windows 10 or the Office 365 product suite.

Most large companies have a series of custom applications that play a crucial role inside their organizations. When you update Windows and Office 365, Murphy’s Law of updates says one or more of those applications is going to break.

Up until this announcement when that inevitably happened, it was entirely the problem of the customer. Microsoft has taken a huge step today by promising to help companies understand which applications will likely break when you install updates, and working to help fix them if it ultimately happens anyway.

One of the reasons the company can afford to be so generous is they have data that suggests the vast majority of applications won’t break when customers move from Windows 7 to Windows 10. “Using millions of data points from customer diagnostic data and the Windows Insider validation process, we’ve found that 99 percent of apps are compatible with new Windows updates,” Microsoft’s Jared Spataro wrote in a blog post announcing these programs.

To that end, they have a new tool called Desktop Deployment Analytics, which creates a map of your applications and predicts using artificial intelligence which of them are most likely to have problems with the update.

“You now have the ability with the cloud to have intelligence in how you manage these end points and get smart recommendations around how you deploy Windows,” Spataro, who is corporate vice president of Microsoft 365, told TechCrunch.

Even with that kind of intelligence-driven preventive approach, things still break, and that’s where the next program, Desktop App Assure, comes into play. It’s a service designed to address any application compatibility issues with Windows 10 and Office 365 ProPlus. In fact, Microsoft has promised to assign an engineer to a company to fix anything that breaks, even if it’s unique to a particular organization.

That’s quite a commitment, and Spataro recognizes that there will be plenty of skeptics where this program in particular is concerned. He says that it’s up to Microsoft to deliver what it’s promised.

Over the years, organizations have spent countless resources getting applications to work after Windows updates, sometimes leaving older versions in place for years to avoid incompatibility problems. These programs theoretically completely remove that pain point from the equation, placing the burden to fix the applications squarely on Microsoft.

“We will look to make changes in Windows or Office before we ask you to make changes in your custom application,” Spataro says, but if that doesn’t solve it, they have committed to helping you fix it.

Finally, the company heard a lot of complaints from customers when they announced they were ending extended support for Windows 7 in 2020. Spataro said Microsoft listened to its customers, and has now extended paid support until 2024, letting companies change at their own pace. Theoretically, however, if they can assure customers that updating won’t break things, and they will commit to fixing them if that happens, it should help move customers to Windows 10, which appears to be the company’s goal here.

They also made changes to the standard support and update cadence for Windows 10 and Office 365:

All of these programs appear to be a major shift in how Microsoft has traditionally done business, showing a much stronger commitment to servicing the requirements of enterprise customers, while shifting the cost of fixing custom applications from the customer to Microsoft when updates to its core products cause issues. But they have done so knowing that they can help prevent a lot of those incompatibility problems before they happen, making it easier to commit to this type of program.

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