Perl doesn't guess at encodings, so I don't know to what you are referring.
Perl does guess. Not "at encodings" perhaps, but tosh didn't say Perl guesses at encodings. Those are your words, ikegami, not tosh's.
The guesswork (or whatever you want to call the legerdemaine) that Perl does is documented in perlunicode:
The "Unicode bug" involves exactly those characters in the Latin-1 Supplement Block (U+0080 through U+00FF) that tosh said "mugged" him.
The problem is that the explanations and workarounds are incomprehensible by mere mortals who just want to write a script to do something simple with modern text (Unicode). It's way too hard to sort out Perl's impenetrable Unicode model.
Evidence that it's way too hard abounds on PerlMonks. Thread after thread about Perl's Unicode support quickly devolve into a debate among the cognoscenti here about how it all works. Even the wizards never seem to agree how to handle Unicode correctly using Perl.
In reply to Re^5: Mugged by UTF8, this CANNOT be right
by Jim
in thread Mugged by UTF8, this CANNOT be right
by tosh
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