Y2K problem, because someone at some point decided that two digits was enough to represent years. Thus when 99 came to an end, the clock would show 00 for year. It was an undefined behavior how to interpret it.
The event was rather boring, because a huge effort went into making sure that critical infrastructure was "Y2K Ready".
So my point was that pushing the problem in front of us until it becomes too large to ignore, is not a good strategy when we're talking (it) infrastructure. Handling leap seconds every now and then are the lesser evil.