In this paper we discuss two types of nominal copular sentences (Canonical and Inverse, Moro 1997) and we demonstrate how the peculiarities of these two configurations are hardly considered by standard NLP tools that are currently publicly available. Here we show that example-based MT tools (e.g. Google Translate) as well as other NLP tools (UDpipe, LinguA, Stanford Parser, and Google Cloud AI API) fail in capturing the critical distinctions between the two structures in the end producing both wrong analyses and, possibly as a consequence of a non-coherent (or missing) structural analysis, incorrect translations in the case of MT tools. To support the proposed analysis, we present also an empirical study showing that native speakers are indeed sensitive to the critical distinctions. This poses a sharp challenge for NLP tools that aim at being cognitively plausible or at least descriptively adequate (Chowdhury & Zamparelli 2018)