Well, the end of support for Windows XP in 2014 was announced in 2008. Windows Vista and 7 were available, and the Windows 8 launch was at hand before the date

Well, the end of support for Windows XP in 2014 was announced in 2008. Windows Vista and 7 were available, and the Windows 8 launch was at hand before the date of his arrest. But the text omits to mention Windows 8.1 which was announced by Microsoft in 2013, after the arrest but well before the Truecrypt announcement was published in 2014. This could be because Windows 8.1 was only considered a relatively minor upgrade to Windows 8 by the author, or because it's existence was unknown at the time when the text was written. This remains open to speculation, but it does not refute the possibility of a dead man's switch.