socket = new Socket(host, port);
socket.setTcpNoDelay(true);

while(!dataList.isEmpty()) {
    String data = dataList.removeFirst();
    inMemoryCount -= data.length();
    try {
        OutputStream os = socket.getOutputStream();
        os.write(data.getBytes());
        os.flush();
    }
    catch(IOException e) {
        inMemoryCount += data.length();
        dataList.addFirst(data);
        socket = null;
        return false;
    }
}

return true;