Lady Lovelace’s notes on Babbage’s Analytical Engine never refer to the concept of surprise. Having some pretension to ‘originate’ something—unlike the Analytical Engine—is neither necessary nor sufficient to being able to surprise someone. Turing nevertheless translates Lovelace’s ‘this machine is incapable of originating something’ in terms of a hypothetical ‘computers cannot take us by surprise’ objection to the idea that machines may be deemed capable of thinking. To understand the contemporary significance of what is missed in Turing’s ‘surprise’ translation of (...) Lovelace’s insight, one needs to distinguish between trivial surprises and those events, propositions or encounters that lead us to question our understanding of ourselves or what surrounds us. Only some of these non-trivial surprises are the product of originality endeavours. Not only is it uncommon for surprises to track such endeavours, the type of autonomy that would be required on the part of ‘digital computers’ for originality and surprise to intersect in that way goes far beyond the operational autonomy that can be achieved by ‘learning machines’. This paper argues that a salient translation of Lovelace’s originality insight—for contemporary and future ‘learning machines’—is an upside-down version of Turing’s surprise question: can computers be surprised by us in a non-trivial, ‘co-produced’ way? (shrink)