Where modern gun-based night attacks might still work

Could a World War Two-style gun night attack work today if the attacker were stealthy enough?

Yes in confined littoral waters, where geography and stealth together can conceal the approach to an unarmored modern target.

Stealth helps a modern gun attack, but it is not the decisive condition by itself. Islands, coasts, and cluttered littoral waters provide the concealment needed to approach without standing out against the open sea. Finnish and Swedish designs illustrate how a small combatant can exploit that geography to close the distance. Once in range, rapid gunfire can do serious damage because most modern warships carry little armor around vulnerable systems.