So when did the former community organizer learn that he had failed to organize the community of software developers implementing the ObamaCare website? According to HHS head Kathleen Sebelius, he found out along with the rest of us. Kinda like Benghazi, or Fast and Furious, except one might have thought that Obama would pay a bit more attention to his legacy achievement.
However, there may have been an odd benefit to keeping the President in the dark (and feeding him BS, natch) about the status of the impending website fail. By September it was clear to all (and reported in the President's preferred paper) that Republicans would be likely to target ObamaCare in the upcoming Continuing Resolutiuon and debt limit fights.
Those were fights the President wanted to have so that he could shut down everything, blame the Republicans, rally his base, and have some stronger message for 2014 than "Let's fail at gun control - again". Imagine the awkwardness if the President's team had been trying to spend September vigorously opposing a delay in ObamaCsre while simultaneously announcing that the website launch would be, well, delayed. My goodness - that whole fight might have been avoided, and what would those fund-raising appeals say now?