Hello!
This problem may be the result of your friend's DNS resolver cache caching old data. Have them try these steps and see if this fixes their problem:
1. Press Windows key and R at the same time. This will open up a run dialog.
2. In the text dialog that says "Open:", type in "cmd". This will open up the command prompt.
3. Inside of the command prompt, run: "ipconfig /flushdns" and press enter. This will refresh the DNS resolver cache on their computer. Upon restarting the game, your friend should be able to join. All this does is it cleans up your ip log and requires your PC to retrieve new data rather than relying on the cached data which may be outdated. It may be worth them restarting their computer after doing this as well just to be on the safe side.
After doing all of this, if your friend is still having problems, here are some other methods they can try:
- Playing on a genuine vanilla version of the game without mods
- Running 1.9.2 as that is the native version the server runs on
- Assuming the above does not work, have them either delete (or move) their .minecraft file. This will ensure that when they start up the game again, pretty much everything will need to be redownloaded (which will automatically happen when the game is started up through the launcher) and that any data that may have been corrupted is brand new.
Let me know if any of this works for them or if they still continue to have problems despite following the above.