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Windows 10 Upgraders Beware

August 4, 2016
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As seen on The Hedge Connection

The allure of a free upgrade to Windows 10 is great, and the effort to avoid upgrading is significant. But upgraders beware — the decision to upgrade a corporate environment to Windows 10 should not be taken lightly. Considerations of risk surrounding a decision to upgrade are more than technology concerns, and suggest that involvement of senior level corporate management is appropriate.

Microsoft introduced Windows 10 in July 2015 as the latest major release of their hugely successful operating system platform. To encourage rapid acceptance of Windows 10, Microsoft offered free upgrades for computers with valid Windows 7 or Windows 8.1 licenses for one year, i.e. until July 29, 2016; after this date upgrades to Windows 10 require payment of additional licensing fees. Additionally, after October 31, 2016, new computers will no longer be available with pre-installed copies of Windows 7 or Windows 8.1.

Windows 10 has been demonstrated to be fast, reliable and largely compatible with a wide array of hardware and software. To keep systems up-to-date, Windows 10 automatically applies patches to all computers, eliminating the need to perform this maintenance task. However, with this mandatory update process comes a loss of control that may be significant to corporate users.

Microsoft issues updates to its products on a regular, frequent basis to provide enhanced functionality, correct bugs and enhance security. Most of these updates are beneficial, and do not interfere with the normal operation of the computer hardware or software. However, some of these updates can wreak havoc with systems, with issues ranging from limiting functionality or causing system hangs to preventing the use of some software altogether.

Sometimes the issues are more subtle, or are unique to a specific network configuration. In July 2015 Microsoft released a patch that prevented one of our clients from cutting-and-pasting data between two critical line of business applications. The results included a significant increase in data entry errors, reduction in productivity and increase in user frustration.

Resolving patch-related problems requires identifying which patch is causing the problem, then uninstalling the patch. With prior versions of Windows, it was possible to then prevent the problematic patch from being reinstalled and thus re-introducing the problem. With Windows 10 however, patch installation is automatic and unavoidable — the best that a company can do is delay installation of the patch, not completely prevent its installation. As such, it’s possible that a problem caused by a patch conflicting with your company’s software may not be resolvable.

While it’s generally advantageous to stay reasonably current with technology, Windows 10 creates the need to decide between retaining older technology and better control over the corporate technology vs. upgrading to newer technology but giving up an element of control.

If your company uses exclusively mainstream software, such as products from Microsoft, Adobe or Intuit, then the risk of introducing Windows 10 with its mandatory updates is likely low — there’s reason to expect that these products and Windows 10 will undergo ongoing compatibility testing and that any issues will be addressed by the respective vendors. If, however, your company utilizes software for accounting, process control, data modeling, Enterprise Resource Planning (ERP) or Customer Relationship Management (CRM), of if your business relies on custom-developed or older versions of legacy software, then it’s critical that you discuss Windows 10 support and maintenance plans with the product vendor, test the software thoroughly in a sandbox environment, and evaluate the risk of mandatory Windows 10 patches before deciding to introduce this operating system into your environment.

Companies depend on their technology to function reliably and securely. Windows 10 is not a bad product, but requires a decision regarding associated risks that must be considered carefully.

For more information about Citrin Cooperman Technology Consulting, please contact David Rosenbaum, Principal, at 914.693.7000 or