I like this approach, I am trying to exclude the inserting of a break if the string in the sentence its a link starting with "http", it gets complicated I guess:

Um, are you trying to invent the syntax or guess?

This is your regex

use YAPE::Regex::Explain;
print YAPE::Regex::Explain ->new(
    qr/([^http.*?\s+]\S{30})/
)->explain;
__END__
The regular expression:

(?-imsx:([^http.*?\s+]\S{30}))

matches as follows:
  
NODE                     EXPLANATION
----------------------------------------------------------------------
(?-imsx:                 group, but do not capture (case-sensitive)
                         (with ^ and $ matching normally) (with . not
                         matching \n) (matching whitespace and #
                         normally):
----------------------------------------------------------------------
  (                        group and capture to \1:
----------------------------------------------------------------------
    [^http.*?\s+]            any character except: 'h', 't', 't',
                             'p', '.', '*', '?', whitespace (\n, \r,
                             \t, \f, and " "), '+'
----------------------------------------------------------------------
    \S{30}                   non-whitespace (all but \n, \r, \t, \f,
                             and " ") (30 times)
----------------------------------------------------------------------
  )                        end of \1
----------------------------------------------------------------------
)                        end of grouping
----------------------------------------------------------------------
[download]

Neither approach is going to work

Try

s{(\S{30,}){
    my $ret = $1;
    if( $ret !~ /http/ ){
        $ret .= " ";
    }
    $ret;
}ge;
[download]

see also perlintro, perlretut, perlre#(?<!pattern)