Windbg "waiting to reconnect" with Laptop and VM as target

It seems that Im leagally required to tell you that I belong in the group of Students, Hobbyists, Dilettantes, and Dabblers. Strong emphasis on the last two.

I tried several guides and things related to them:

VM is VirtualBox btw.

The end result is always the same. Windbg says “waiting to reconnect” and nothing happend bexonf this point.

If I would at least know how to properly check if all preconditions are met on host and target side. But Im really not sure.

bcdedit on target VM for example does not look right to me:

PS C:\Windows\system32> bcdedit

Windows-Start-Manager
---------------------
Bezeichner              {bootmgr}
device                  partition=\Device\HarddiskVolume1
description             Windows Boot Manager
locale                  de-DE
inherit                 {globalsettings}
default                 {current}
resumeobject            {0f9b6fad-dcd5-11eb-9458-a05e50d80135}
displayorder            {current}
toolsdisplayorder       {memdiag}
timeout                 30

Windows-Startladeprogramm
-------------------------
Bezeichner              {current}
device                  partition=C:
path                    \Windows\system32\winload.exe
description             Windows 10
locale                  de-DE
inherit                 {bootloadersettings}
recoverysequence        {0f9b6faf-dcd5-11eb-9458-a05e50d80135}
displaymessageoverride  Recovery
recoveryenabled         Yes
allowedinmemorysettings 0x15000075
osdevice                partition=C:
systemroot              \Windows
resumeobject            {0f9b6fad-dcd5-11eb-9458-a05e50d80135}
nx                      OptIn
bootmenupolicy          Standard
debug                   Yes
PS C:\Windows\system32>

kdnet says NIC is supported. The

PS C:\Windows\system32> & "C:\Program Files (x86)\Windows Kits\10\Debuggers\x64\kdnet.exe"

Network debugging is supported on the following NICs:
busparams=0.3.0, Intel(R) PRO/1000 MT Desktop Adapter, KDNET is running on this NIC.

Network debugging is not supported on any of this machine's USB controllers.

KDNET transport initialization failed during a previous boot.  Status = 0xC00000B5.
InitializeNetwork failed to get the MAC address of the host debugger. Check the dbgsettings hostip!
PS C:\Windows\system32>

You’d need to say bcdedit /debugsettings to see how the network debugging is configured. If you are debugging a VM from its host system, often the easiest option is to use a fake serial port.

Hello Tim Robertis ,please have following configuration below.

vm Windows 10 10240 2gb ram

Host Windows 11 Versão 21H2 compilation22000.675

C:\Windows\system32>bcdedit /debug on
A operação foi concluída com êxito.

C:\Windows\system32>bcdedit /dbgsettings net hostip:192.168.33.4 port:53000
Key=1unzo43k757ka.1riqby08clhqx.3lkqpx9ahqknl.1or7sbffybaev

C:\Windows\system32>bcdedit /set testsigning on
A operação foi concluída com êxito.

C:\Windows\system32>bcdedit /dbgsettings
key 1unzo43k757ka.1riqby08clhqx.3lkqpx9ahqknl.1or7sbffybaev
debugtype NET
hostip 192.168.33.4
port 53000
dhcp Yes
A operação foi concluída com êxito.

Microsoft (R) Windows Debugger Version 10.0.22000.194 AMD64
Copyright (c) Microsoft Corporation. All rights reserved.

Using NET for debugging
Opened WinSock 2.0
Waiting to reconnect…

Did you copy-and-paste the very long key from the settings to your WinDbg kernel configuration? I always specify my own simple key, one that I know I can remember.