When Should You Upgrade Operating Systems and Other Software?

On an enterprise-wide basis, OS and other software upgrades are periodically performed only when cost, number of licenses, IT installation time, and follow-up troubleshooting all meet the auspices of the IT powers that be. In some instances, an upgrade to the latest version of a program is necessary just to get the job done and interact with customers and colleagues worldwide. How does your company approach this never-ending dilemma? How do you handle the situation for your personal PCs? Do glitches reported by other users ever figure into the equation of whether to upgrade now or later?

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