I've seen this video; heavily recommend it.
In a nutshell, what computers can't reliably understand is anything that relies on "world knowledge" - that is, knowledge outside the language that you need to know to parse it correctly. Stuff like "apples fall down, not up", "a container needs to be bigger than the item that it contains", stuff like this.
Note that the common NLP (natural language processing) methods do not even try to address this, as they often rely on brute force - "if you feed enough language into the computer, it'll eventually get it".