The English language word assert here is used in the sense of swear, affirm, avow. It doesn't mean "check" or "should be". It means that you as a coder are making a sworn statement here:
# I solemnly swear that here I will tell the truth, the whole truth,
# and nothing but the truth, under pains and penalties of perjury, so help me FSM
assert answer == 42
If the code is correct, barring Single-event upsets, hardware failures and such, no assert will ever fail. That is why the behaviour of the program to an end user must not be affected. Especially, an assert cannot fail even under exceptional programmatic conditions. It just doesn't ever happen. If it happens, the programmer should be zapped for it.