in reply to Re: Regex - Matching prefixes of a word
in thread Regex - Matching prefixes of a word

That's overly complicated. Move the \b to the end.
$line =~ /\bh(?:e(?:l(?:l(?:o)?)?)?)?\b/i;
In 5.10, you can even disable needless backtracking
$line =~ /\bh(?:e(?:l(?:l(?:o)?+)?+)?+)?+\b/i;