Thus the depressing answer to the question “Do conjoined twins always die at the same time?” is “More or less, yes.” Sorry, but I don’t want to sugar-coat it. Doctors are developing new imaging technology which may help us better understand what’s going on deep inside conjoined twins. But the twins are connected in ways (physically and emotionally) that even the latest, most expensive technology will struggle to perceive. Conjoined twins are real people, with real lives and personalities.