Hmmmm ... well, you could try a time out:

$SIG{ALRM} = sub { die "timed out" };

eval {
   alarm(60); # give it 60 seconds
   $response = $useragent->simple_request($request,\&callback,2048);
   alarm(0);
};

# now look for "timed out" in $@

if ($@ =~ /timed out/) {
   # do something
}
[download]

---

UPDATE:
Bummer that you only have Win2k at your disposal. . As for killing the incoming stream - when are you setting $useragent to undef? Seems to me that you would never be able to that without a time out mechanism - the script would continue to wait indefinetly for the server to end the connection.

i thought you might be able to use something like:

undef $useragent if $@ =~ /timed out/;
[download]

but the whole having to deal with Win2k is a right bummer. Sorry i couldn't help more :(

jeffa