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Microsoft should follow Apple move and make its latest Windows 8.1 operating system free to all Windows users. The time has come for Microsoft to take "a page from Apple’s playbook" and offer existing Windows users a free upgrade. Google has been selling Chromebook laptops with Chrome OS (free updates forever) and is currently selling like a hot cake. I have already moved away from Windows to Chrome OS and will do that for home PC. I bet there are many fence-sitters who are in the same boat and Microsoft has a chance to pull them by offering free upgrade.
Pretty sure my dad's 12-year-old machine has no hope of running Windows 8, and even if it could, what exactly would be the upgrade path?
> Microsoft should follow Apple move and make its latest Windows 8.1 operating system free to all Windows users

Apples operating system is not free, you have to purchase an over price computer aka a mac to get it for free.

Except Apple make money on the hardware, Google on the services, and Microsoft would be shooting itself in the foot by cutting off its main revenue source, not to mention the bad press it would generate if Windows 8 failed to run sufficiently well on some of those (understandably) outdated machines.
Can a WinXP mode app in Win7 be safely isolated from the network, accessing local files only so it can't be exploited?
You mean Windows XP Mode? Well you can completely disable networking in settings, or set to "Internal network" to be able to only communicate with host. However if host is infected with some network-spreading virus, I suspect XP still could get infected.
Hopefully this will lead to more people installing Ubuntu, which has a modern browser (Firefox) bundled as the default browser.
I've had a bad experience with Unity, it would be too big of a switch. I doubt it would work on xp machines anyway.
I've been using Ubuntu 12.04 LTS in a VirtualBox with 512mb of memory - it runs surprisingly well.
When DNSChanger was spreading, the FBI eventually shut down their command & control servers, which disconnected approximately 300000 computers from the Internet. Although it was an indirect shutdown of peoples' Internet connections, there wasn't much of an outcry when it happened.

If Windows XP gets sufficiently targeted by malware authors using derivative Vista/7 zero-days unlatched in XP, is there a point where it makes more sense to forcefully disconnect WinXP machines from the Internet for the greater health of the Internet?

All it would take is something like the Morris worm.
There are still so many ATMs running Windows XP. Not that the regional banks running them are actually patching them in the first place, but still.
Correct me if I'm wrong, but I doubt ATMs are connected directly to the internet.
They are, and if you flip one hardware switch inside you go into diagnostic mode and can print out the IP and all config information and trivially reconfigure without any sort of security or logging. The days of expensive dedicated lines are long gone. Most ATMs run off of the bank location's LAN, which given the quality of regional banking IT is not secured all that well.

A lot of the machines I worked on in remote locations (in highrise offices away from bank locations) were hooked up through the building's wifi via a wireless router sitting unsecured on top of the machine, just out of sight. I mean, you have easy physical access to the connections in that case.

Time to install Ubuntu.
I'm not sure why you got down-voted, as that seems like a reasonable strategy for some businesses.

Many of these companies are running old hardware that can't handle a newer flavor of Windows, but many variants of Linux are comparatively lightweight. Most of the applications they use will either be cross-platform or there will be a reasonable replacement. Several distros have commercial support, which is important for businesses.

That's not to say that transition would be painless, but I think it's going to be a viable option for some people.

The looming end of XP comes up periodically, usually with some mention of needed enterprise and small business software that does not run on anything else. (I recently noticed that my dentist's systems were running XP; and wondered, without asking, if she could upgrade even if she wanted to.)

But I think part of the problem is that it's so inconvenient for an individual to move from an XP machine even if (s)he can--even moving to another XP machine is a pain. I remember our VP turning down a laptop upgrade (this was 2006 or so) because she didn't want to fuss with the settings on a new machine. Coming from a VMS/Unix/Linux background, this just struck me as out-of-place (though, of course, I'd gone through the same difficulty at home).

Seems like there would be a good opening for a third-party company to offer XP support updates going forward on a subscription basis. If hackers can reverse engineer updates and figure out the weaknesses, couldn't another company do the same but offer the patches?