The marginal cost of sending updates to pirated machines is probably negligible, and pirates adapted to WGA within a couple weeks.
So – they managed to convert a few Western users who didn't know they were running a pirated copy. I would place a good bet that the total volume of pirated licenses remained the same, though.
More recent experiments have shown that piracy is really more about customer service than straight up cost [0]. As a result, we have large hordes of unpatched machines that are easy to convert into zombies and running outdated software the rest of us have to support.
[0] http://www.geekwire.com/2011/experiments-video-game-economic...
Do we really, though? If the boxes running IE6 are in Asia and elsewhere in the developing world, how many of us really need to develop for them? I can't think of many websites that need to cater to Chinese pirates.
Why would you support outdated software only used by pirates? Just don't support it to force the pirates to update.
I regularly pay for stuff on the internet (domains, hosting, invoicing apps, ios apps, etc. etc.) as long as Paypal is supported (we cannot use credit cards to make international payments).
You need to support as many people as possible with your webapp, you never know who your customer is.
You're criticizing MS for not pushing updates to pirated versions of their software?