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But the XP end-of-life event has turned out to be pretty lucrative for them, with companies and government agencies opening their wallets in exchange for extended support. I wonder if they'll be enticed to shake that tree again more frequently in future.

I think this is one of those "Some money is too expensive" kind of situations, really. The drain on Microsoft's resources, and the knock-on effects of having increasingly vulnerable windows installs around, are probably worth far more, in the long run, than any amount anyone would ever pay them.

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