In this situation, the decisions to make crypt implementations stop returning null in favor of a string error token were made not because C programs that misuse crypt are difficult to fix, but because they are in the form of unknown binaries in the wild that you cannot fix.

And that analogous situation can happen in the safer language where crypt returns an Optional(String) which some bad programs assume is always present. You don't know where all such programs exist, and people use them who don't have the code and cannot fix them.

Returning an error token which is carefully different from crypt's second argument was an attempt to fix programs that cannot be hunted down, patched and recompiled, even if fixing them would be easy to do.

Of course the tooling for C pointers being null or not is not comparable to optional types; that's not debatable.