By drawing on the philosophy of Bernard Stiegler, the phenomena of mechanical (a.k.a. artificial, digital, or electronic) intelligence is explored in terms of its real significance as an ever-repeating threat of the reemergence of stupidity (as cowardice), which can be transformed into knowledge (pharmacological analysis of poisons and remedies) by practices of care, through the outlook of what researchers describe equivocally as “artificial stupidity”, which has been identified as a new direction in the future of computer science and machine problem solving as well as a new difficulty to be overcome. I weave together of web of “artificial stupidity”, which denotes the mechanic (1), the human (2), or the global (3). With regards to machine intelligence, artificial stupidity refers to: 1a) Weak A.I. or a rhetorical inversion of designating contemporary practices of narrow task-based procedures by algorithms in opposition to “True A.I.”; 1b) the restriction or employment of constraints that weaken the effectiveness of A.I., which is to say a “dumbing-down” of A.I. by intentionally introducing mistakes by programmers for safety concerns and human interaction purposes; 1c) the failure of machines to perform designated tasks; 1d) a lack of a noetic capacity, which is a lack of moral and ethical discretion; 1e) a lack of causal reasoning (true intelligence) as opposed to statistical associative “curve fitting”; or 2) the phenomenon of increasing human “stupidity” or drive-based behaviors, which is considered as the degradation of human intelligence and/or “intelligent human behavior” through technics; and finally, 3) the global phenomenon of increasing entropy due to a black-box economy of closed systems and/or industry consolidation.