Of course it's possible, but it might be hard.
I would recommend:
- Verify that you don't get errors from your calls to send data (perhaps you're specifying a bad address, or the socket is in a bad state or something).
- Try sending more seldom, perhaps your packets are getting dropped by your local network stack.
- Make sure you really listen properly at the receiving end, perhaps the packets make it but you fail to read them properly.
- Consider firewall/NAT issues, as usual with UDP. Protocol-wise, never include connection information as application data in packets, since then it's invisible to NAT-machines.
The next step might be digging down and trying to get some feedback from the local network stack, or maybe sniffing the network to see if the packets make it some way at least.