This scratches at the surface of the very complex field of hermeneutics (basically how can humans* understand the semantics of utterances or other representations).
In the west it got its start in religious enquiry (loosely: the Bible is ambiguous, or at least people disagree about interpretation; can we figure out what the real underlying message is and thus correct errors made by humans because obviously the "real" text must be absolutely correct).
In the 20th century this discipline was broadened primarily by Heidigger whose work is famously incomprehensible yet filled with insight along with many others; it also lead to insight (e.g. semiotics) and extreme absurdity (e.g. 99.9% of the deconstructionists, sadly despite their having started with a useful insight).
* and in more modern times, machines. I spent several years in the 1980s working on how it even makes sense to talk about a machine "understanding". It definitely changed how I view the world, but IMHO so far has had essentially no impact on the world itself.