&gt; Define &#x27;squishy&#x27;. You can&#x27;t, can you?<p>Underspecified.<p>Understanding, correctly, what an underspecified system should do is a strong AI problem (in most cases, at least).  All (or nearly all) unbuilt systems are underspecified (as well as many built ones).  We do not yet have strong AI.  Hence, we have developers who will continue to collect paychecks for the foreseeable future (your &quot;tired meme&quot;).<p>&gt; What is it about information machines (as opposed to humans) that make them unable to handle ambiguity? Why can&#x27;t a machine handle ambiguous input?<p>Your focus on &quot;ambiguous input&quot; misleads you.  The difficulty is more like <i>ambiguous output</i>.