The Obama administration dreamed that its health insurance exchanges--the websites that were supposed to make it easy to buy health insurance--would function as smoothly as online consumer sites like Expedia or Amazon.com. But as head-scratching continues about how a famously web-savvy administration could have flubbed its Internet homework so badly, an examination by the Sunlight Foundation shows the administration turned the task of building its futuristic new health care technology planning and programming over to legacy contractors with deep political pockets.

One result: Problem-plagued online exchanges that make it all but impossible for consumers to buy insurance and ...