First thing that you should do is to ensure your TFTP server is actually working and ensure it is configured for logging. This way you can check if RPi `TFTP` requests where received by `TFTP` deamon. `TFTP` uses `UDP` and so is not really reliable. You can debug it by capturing the network traffic on your TFTP host using `tcpdump` or `wireshark`: For `tcpdump`, you can use something like (you can termianate it by CTRL+C) sudo -i tcpdump host 192.168.2.2 Where `192.168.2.2` is your RPi IP address. You should see all the network packages sent to/from RPi. This way you can see if `TFTP` packages are sent at all. *NOTE*: You may need to use `-i interface` (before word `host`) option to specify interface other than default if you have more than one on your server. *NOTE2*: You can add ` and port tftp` at the end of your command to only limit network traffic to TFTP packages.