I worked a HackTheBox target over the last week using CommandoVM as my attack station. I was pleasantly surprised with how much I liked it. In fact, only once on this box did I need to fire up my Kali workstation. Because the target was Windows, there we parts that were made easier (and in one case made possible!). There were a couple additional struggles that arose, and I’m still in search of a good tmux equivalent. I’ll walk through some of the lessons learned from working in this distro.



On Linux, I use all sorts of tools to enumerate SMB (in fact my blog post on SMB enum is the most visited page on this site). But none of them were on Commando. Then I realized I can use the Windows native tools.


I can use net view [ip] to get a listing of shares. For example, on one host, where I can’t list any shares without auth, I get this:

C:\>net view [ip]
System error 5 has occurred.

Access is denied.

On another machine, I get:

C:\>net view [ip]
Shared resources at [ip]

Share name         Type  Used as  Comment

CertEnroll         Disk           Active Directory Certificate Services share
Department Shares  Disk
NETLOGON           Disk           Logon server share
Operations         Disk
SYSVOL             Disk           Logon server share
The command completed successfully.

I can use net use to connect to shares as well.


I could also use Windows Explorer. I enter \\[ip] into the location bar. For the first one that denied me access, I get a prompt for creds:


For the second one above, I get a list of shares:



I also really like SMB as a transport to and from target. From Kali, I’d do that with a temporary SMB server with smbserver.py. From Windows, I can set up an actual SMB share.


First, because I run as administrator in my VM, I want to use a different user to connect to this share. So I created another user, dummy, in control panel. I gave dummy a good password.

Next, I created a folder in c:\ called share. I opened the folder properties, and first, under security, made sure both administrators (me) and dummy had full control over the folder.


Then I went into “Sharing” -> “Advanced Sharing” and checked “Share this folder”. I left the name as “share”, and clicked “Permissions”. I removed all users, and added dummy:


Now the share is ready to go. I can drop nc.exe or other tools in there I may want to move to target.


With a shell on target, I can now connect to the share on CommandoVM with net use. I’ll just make sure to include dummy’s username and password:

[hostname]: PS C:\Users\[username]\Documents> net use /u:dummy \\\share [password]
The command completed successfully.

Now I can check out the share, and copy to and from it:

[hostname]: PS C:\Users\[username]\Documents> dir \\\share

    Directory: \\\share

Mode                LastWriteTime         Length Name
----                -------------         ------ ----
-a----        4/10/2019  10:44 PM        7613952 chisel_windows_amd64.exe
-a----        9/17/2011  12:52 AM          38616 nc.exe
-a----        9/17/2011  12:52 AM          45272 nc64.exe
-a----        4/12/2019   1:54 PM          37641 powercat.ps1

Windows Firewall

I spent a long time thinking the box I was working was locked down like Ethereal because I couldn’t get anything to connect to my python -m http.server. In reality, connections were getting out fine, but it was my firewall blocking them. Many programs will prompt when I start to listen on a new port to ask if I want to open the firewall. But something like python -m http.server typically doesn’t (also note, as I mentioned in the previous, python runs version 3, so http.server instead of SimpleHTTPServer). So I need to make sure that the firewall is open (this cost me more hours than I’m proud to admit).

I decided to just add my own rule in the Advanced Settings that allows 80 and 443 in:


If I were working a box like Ethereal, where I needed to try to connect out on every port with the hopes of finding one, I would take the firewall down all together for that test. If you’re feeling paranoid, take a snapshot, take the firewall down, run the test, then revert once you the results.


I’ve typically used Alamot’s WinRM ruby scripts to get a WinRM shell from Kali. They are fine, and rlwrap makes the experience livable. That said, the experience is so much better in a true PowerShell connection.


In order to connect over WinRM to another computer, there is some setup and configuration that must be done. Much of this is to tell Windows you’re ok trusting this computer.

  1. Add host to c:\windows\system32\drivers\etc\hosts. Windows is used to doing things by hostname.
  2. I’ll need to start the “Windows Remote Management Service” if it isn’t already running. Running winrm quickconfig from cmd is a simple way to take care of this.
  3. Add all hosts to the trusted hosts list with winrm set winrm/config/client @{TrustedHosts="*"}. This would be a terrible configuration for any real life box, but will be fine for my hacking box. If I wanted to be more secure, I could replace * with the hostname.
  4. Enable CredSSP. This will allow me to connect with -authentication CredSSP later. In PowerShell, run Enable-WSManCredSSP -Role "Client" -DelegateComputer "*". Another case where I could replace* with the hostname in a real situation.
  5. Open local group policy (gpedit.msc) and got to “Computer Configuration” -> “Administrative Templates” -> “System” -> “Credential Delegation” -> “Allow delegating fresh credentials with NTLM only server authentication”. Make sure it’s enabled, and then click “Show” and add “WSMAN/[hostname]”.

The last two steps were specific to CredSSP authentication, so if I’m not going to use that, I don’t need them. That said, CredSSP allows me access to additional things like EFS encrypted files, so I’m going to want it.


To connect, I just run Enter-PSSession, and give it the password when it prompts:

PS C:\ > Enter-PSSession -ComputerName [hostname] -Credential [hostname]\[username]

Windows PowerShell credential request
Enter your credentials.
Password for user [hostname]\[username]: ******************

[hostname]: PS C:\Users\[username]\Documents>

This shell has tab completion and up arrow for history. It’s quite pleasant to work from. Tab-completion is especial useful in PowerShell, since it has such verbose commandlet names. The shell can lag from time to time, not nothing too unusual.

If I’m going to be connecting multiple times, or want to script connection, I can also create a PowerShell PSCredential object using the following template, assuming $username and $password are already set:

$secure = ConvertTo-SecureString -AsPlainText $Password -Force
$user = New-Object -TypeName System.Management.Automation.PSCredential
-ArgumentList $username,$secure
Enter-PSSession -ComputerName [hostname] -Credential $user

This is useful working a box over the course of a couple days and not wanting to look up the user’s password over and over.

There’s also the ability to create a stateful session with something like $session = New-Pssession -ComputerName [host] -Credential [credential]. Then you can Enter-PSSession that session. You can also load local scripts into that session, and other cool stuff.


Additional Installs

There will definitely be more tools to bring. I started creating more folders in c:\tools\ and adding things there. Some stuff to consider:

For git repos, downloading is as simple as Kali - just go to the directory the folder should live in, and git clone [url from GitHub].

Stuff Already There

I was excited a couple of times where I went to get something off the internet only to realize it was already there (like Nishang).

I also really liked having access to Visual Studio. I wanted to try the COR Profiler technique, but needed a new dll. It felt like kind of a long shot, and having to boot into a different VM might have caused me to put off trying. But having Visual Studio right there made it such that I had a dll reverse shell 2 minutes later!


There is a version of responder that runs on Windows, but in a less than exhaustive effort, I couldn’t get it to run. Eager to see if it was even going to be useful on the box I was working, I switched over to Kali (and found it wasn’t). I may revisit at some point. I’d be curious if anyone has successfully run this thing. I couldn’t find any writing about it other than the GitHub page.

@mcohmi pointed out that Inveigh does this, and it is already installed on CommandoVM. I’ll check that out sometime soon hopefully.


Overall Experience

I was quite surprised by how much I liked working a HTB target from a Windows VM. I might try it again next Windows machine I work. The biggest thing I didn’t like was the terminal situation. I miss tmux so much. cmder just isn’t doing it for me yet, and I spent most of my time working out of individual PowerShell and Cmd windows. That said, having tab completion on a WinRM session was huge. So nice. I’d definitely recommend giving this a try if you have time to build the VM and play with it.

Next Steps

Moving forward, I may be jumping back and forth between Kali and CommandoVM. Having a Windows machine as part of the tool set I use regularly will make life easier. It would be nice if I could have both connected to HTB at the same time. I might have to investigate if there’s a way to set up one of my VMs (I’m assuming Kali) as a router that I can then have the other route traffic through, including into the VPN. If I do, I’ll certainly write about it. If you have ideas, please comment or hit me up on Twitter/Slack/NSF.