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Wait, the Windows 10 Anniversary Update wasn't already enterprise-ready?

Microsoft’s declaration in November that the latest version of Windows 10 is enterprise-ready created confusion in some businesses that had already been using it for months.

After Microsoft releases a Windows 10 Anniversary Update, as it did in August, the company spends 90 days noting and responding to all the issues customers and independent software vendors have. IT experts who were not aware of this process said they’d like better communication from the vendor.

“Microsoft has always done a poor job of communicating this kind of stuff,” said Doug Grosfield, president and CEO of Five Nines IT Solutions, a Microsoft partner in Kitchener, Ont. “And then there is always a cleanup operation involved. It’s unfortunate for the customer and creates extra work.”

For example, Grosfield’s customers faced issues with VPN client software from providers including Dell, Cisco and SonicWall. Following the installation of the Windows 10 Anniversary Update, some businesses needed to reinstall their VPN client software for them to work again, Grosfield said. Initially, this caused many problems and halted productivity for remote workers.

Microsoft should have addressed these and other issues and labeled the Windows 10 Anniversary Update as enterprise-ready when the company released it, Grosfield said.

“Microsoft has got some ground to make up on the Anniversary Update because it was released in a way that broke a lot of things,” he said. “It would take hours to actually do the update, which was very disruptive, and it created some problems to solve with a bunch of software.”

The Anniversary Update also caused problems for many antivirus software platforms initially, but they have since been resolved.

It’s always a good idea to wait to install any software update because of situations like this, where the update causes problems with other software or has its own bugs, said Robby Hill, founder and CEO of HillSouth, an IT consultancy in Florence, S.C.

“It’s been a best practice in IT services for quite a while,” Hill said.