OptionalLolz.java

import java.util.Optional;
import java.util.function.Function;

class Main {
  public static void main(String[] args) {
    Optional<String> o = Optional.of("foo");
    Function<String, String> f = s -> null;
    Function<String, String> g = String::valueOf;
    
    //lawless lolz
    System.out.println(    o.map(g.compose(f))   ); //Optional[null]
    System.out.println(    o.map(f).map(g)       ); //Optional.empty
    
    //This is because
    System.out.println(    o.map(f)              ); //Optional.empty
    
    //Once again for clarity
    System.out.println(    o.map(s -> null)      ); //Optional.empty
    
    //And now for more lolz
    System.out.println(    o.flatMap(s -> null)  ); //throws NullPointerException
  }
}

That's correct. Optional has been designed to explicitly never be able to contain a null value. Arguably more correct behaviour would have been to have map to throw an NPE if the function application returned null - but you'd still have the issue that o map f map g and o map (g compose f) would be different.

Presumably one "advantage" for explicitly disallowing Optional(null) might raise its head when the JVM gets value classes.

FWIW, we tried this (failed) experiment about 12 years ago. The correct solution is to assume that null does not exist, at all.