Good idea to make them upgrade. Here's a suggestion: like with arms in warzones, allow people to trade in their old softmare for money (so they can decide what to do with it) or give them (right, give !) a fully-equipped new box with the up-to-date software and hardware that is required to run it.

Wait, why give ? Microsoft needs to make a living ! (sure, they're almost bankrupt).
Not worth the money ? Apparently it is, since there's so much fuzz about it.
Why should Microsoft pay for this ? Well, it's their software, right ? What happens if your car that's almost 10 years old seems to have a defect that could endanger your but more importantly the live of other people on the street ? Will the manufacturer, if it turns out that your car is not the only one, in fact every other car of the same make seems to have the same problems, wait for 10 years to call these cars in for a major overhaul ?
If the answer is yes, the manufacturer would have been sued to bankruptcy already in the meantime.

At least a good way to spend that money, give it back to those you stole it from

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