in reply to Re^2: Can't get Net::SMTP to work
in thread Can't get Net::SMTP to work

In the that I can look into, the code is like

sub connect { @_ == 2 or croak 'usage: $sock->connect(NAME)'; my $sock = shift; my $addr = shift; my $timeout = ${*$sock}{'io_socket_timeout'}; my $err; my $blocking; $blocking = $sock->blocking(0) if $timeout; if (!connect($sock, $addr)) {
so the call to connect should still be traceable a bit by single-stepping...Might help to know if the issue is before or after getting a local socket to use. Not that I think that would help too much, but it still might get you a bit closer to a solution.

Any chance to try the code on another machine ? Are you running this with the same privileges as when you do successfully telnet ? Maybe you can check if it behaves the same way when you run it as Administrator?