The main assumption in this paper is that there are important, unfamiliar andobscure qualities of information technology as it intertwines with people’s everyday life.That is, aspects that so far and to a large extent has escaped critical scrutiny. It is alsotentatively suggested that these unknown qualities are being prevented from criticalexaminations as long as we pursue investigations based on design and/or useperspectives. In this paper a tentative response to the request for new perspectives oncritical research is formulated. The response is based on my assessment of Critical Theoryand Critical Theory of Technology where an aesthetic understanding is suggested to alterour critical sense of how people today form meaningfulness by, through and withinformation technology. So, without neglecting other commonly held critical positions thispaper tentatively concludes that an understanding of the reflexive nature of informationtechnology in conjunction with the basic spirit behind the Frankfurt School empowercritical IS researchers with a new sensibility for what might constitute contemporary criticalconcerns.