The IO::Socket modules use the timeout feature built into the select() system call to do timeouts when recving or sending data; however, in order to do a connect, they attempt to set the socket to non-blocking mode (which does not work properly without some cajoling on Win32 systems).

For this reason, if you cannot actually connect to your peer's http port, a Win32 timeout on an LWP call will not work. If, however, you can connect to the peer's listening socket, then the timeout should work.