I don't have Windows, and your scripts run on Linux; but it seems you have 2 fileevents on the $socket filehandle. That does not look right, as it may prevent the new_connection sub from getting triggered.

Also there is a faq for this at ActiveState Windows socket faq, which may have a clue for your version of Windows.

$mw ->fileevent($socket, readable => sub {
                    my $line = <$socket>;
                      unless (defined $line) {
                       $mw->fileevent($socket => readable => '');
                       return;
                       }
         $text->insert(end => $line);
  });

my $client;

$mw->fileevent($socket, 'readable', sub { new_connection($socket) });
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