As a player who originally started playing Minecraft since the very early days of Java alpha up and stopped playing until not long after Notch left Mojang, I have returned recently after having played split-screen on my daughter's switch with her. While fun, the switch does struggle with two players and also hosting a server.

Wanting to take it to the next level and getting a proper server and also inviting a good friend of mine, I set up a virtual machine on Hyper-V and installed Ubuntu 22 and the OpenSSL deps, completely fresh system and it doesn't work. Nothing I could do, even forwarding the ports to the public internet (bear in mind this is the same PC on the same network, its just a VM) would fix it. I even tried the instructions in the manual to change loopback settings, nada...

Here are the reproduction steps Mojang.

1. Set router to 192.168.0.1/24... e.g. 192.168.0.1 and subnet 255.255.255.0
2. Set Host OS to 192.168.0.10/24
3. Install Ubuntu on Hyper-V in bridged networking mode.
4. Set Ubuntu VM to static as 192.168.0.50/24.
5. Install LibSSL 1.1.1:

   sudo curl -o libssl.deb -k -L http://archive.ubuntu.com/ubuntu/pool/main/o/openssl/libssl1.1_1.1.1l-1ubuntu1.6_amd64.deb
   sudo dpkg -i libssl.deb

1. Set whitelist for the desired players and enable it.
2. Run the server
3. Try to add the server to 'Servers'. Can see the server online and responding.
4. Try to connect to the server. Times out after a few minutes.

minecraft@minecraft:~/server$ LD_LIBRARY_PATH=. ./bedrock_server
NO LOG FILE! - setting up server logging...
[2022-07-14 15:33:18:082 INFO] Starting Server
[2022-07-14 15:33:18:082 INFO] Version 1.19.10.03
[2022-07-14 15:33:18:082 INFO] Session ID 0074ddff-17a0-4b9b-bc43-7e0f67f3c60f
[2022-07-14 15:33:18:082 INFO] Level Name: Bedrock level
[2022-07-14 15:33:18:084 INFO] Game mode: 0 Survival
[2022-07-14 15:33:18:084 INFO] Difficulty: 1 EASY
[2022-07-14 15:33:18:109 INFO] opening worlds/Bedrock level/db
[2022-07-14 15:33:18:461 INFO] IPv4 supported, port: 19132
[2022-07-14 15:33:18:461 INFO] IPv6 supported, port: 19133
[2022-07-14 15:33:18:627 INFO] Server started.
[2022-07-14 15:33:18:655 INFO] IPv4 supported, port: 36352
[2022-07-14 15:33:18:655 INFO] IPv6 supported, port: 35462
[2022-07-14 15:33:18:677 INFO] ================ TELEMETRY MESSAGE ===================
[2022-07-14 15:33:18:677 INFO] Server Telemetry is currently not enabled.
[2022-07-14 15:33:18:677 INFO] Enabling this telemetry helps us improve the game.
[2022-07-14 15:33:18:677 INFO]
[2022-07-14 15:33:18:677 INFO] To enable this feature, add the line 'emit-server-telemetry=true'
[2022-07-14 15:33:18:677 INFO] to the server.properties file in the handheld/src-server directory
[2022-07-14 15:33:18:677 INFO] ======================================================

In my old Java days of setting this up would have been a similar process and would have worked flawlessly. There is nothing to suggest what the problem is and the server appears online but remains not connectible.