my $brackets = qr(\[[^\]]*\]); # text enclosed in brackets my $char = qr([^\[\]\s]); # not spaces or brackets s{ ( # group to $1 (?: $char # a char (?:$brackets*) # followed by any number of brackets ) {3} # 3 times ) (?!(?:$brackets*)(?:\s|\Z)) # ADDED: eliminates '-' on the end of words w/ a multiple of 3 chars (?= # looking forward to ensure that [^\[\]]* # we are not inside of a brackets (?: \[ | \z ) ) } {$1-}gx; print;