Hacker Conducts Complex Attack on Active Directory, Causing HTB Rebound

Today we’ll start with the typical (and not so typical) AS-REP Roasting and Kerberoasting attacks. Then we’ll dig into the LDAP database and find a non-obvious path forward. When gaining access to the host, we use the RemotePotato technique, and to increase privileges, we use the S4U2proxy technique.

Our goal is to obtain superuser rights on the Rebound machine from the training site Hack The Box. Its difficulty level is “insane.”



It is recommended to connect to machines with HTB only via VPN. Do not do this from computers that contain data that is important to you, as you will end up on a shared network with other participants.

Intelligence service

Port scanning

Add the machine's IP address to /etc/hosts:

И запус­каем ска­ниро­вание пор­тов.


Справка: сканирование портов

Ска­ниро­вание пор­тов — стан­дар­тный пер­вый шаг при любой ата­ке. Он поз­воля­ет ата­кующе­му узнать, какие служ­бы на хос­те при­нима­ют соеди­нение. На осно­ве этой информа­ции выбира­ется сле­дующий шаг к получе­нию точ­ки вхо­да.

На­ибо­лее извес­тный инс­тру­мент для ска­ниро­вания — это Nmap. Улуч­шить резуль­таты его работы ты можешь при помощи сле­дующе­го скрип­та:


ports=$(nmap -p- --min-rate=500 $1 | grep ^(0-9) | cut -d '/' -f 1 | tr 'n' ',' | sed s/,$//)

nmap -p$ports -A $1

It works in two stages. The first one performs a regular quick scan, the second one performs a more thorough scan using the available scripts (option -A).

The result of the script

The scanner found many open ports, which is typical for Windows servers:

  • 53 - DNS;
  • 88 - Kerberos;
  • 135 - Remote Procedure Call Service (Microsoft RPC). Used for controller-controller and controller-client interaction operations;
  • 139 - NetBIOS session service, NetLogon;
  • 389 - LDAP;
  • 445 - SMB;
  • 464 - Kerberos password change service;
  • 593 (HTTP-RPC-EPMAP) - used in DCOM and Exchange services;
  • 636 - LDAP with SSL or TLS encryption;
  • 3268 (LDAP) - to access the Global Catalog from the client to the controller;
  • 5985 - WinRM remote management service.

First of all, we check whether anonymous login is possible and display a list of shared directories. To do this we use the utility CrackMapExecwhich will be useful to us more than once during our passage.

crackmapexec smb rebound.htb -u guest -p '' --shares

Shared SMB Directories
Shared SMB Directories

We see a non-standard directory Shared. You can connect and view the content using the script from the set impacket.

impacket-smbclient guest@rebound.htb

Shared Directory Contents
Shared Directory Contents

But the catalog turned out to be empty, so we move on to other techniques.

Point of entry

Since anonymous authentication is available on the SMB resource, you can drill through the RID and get group names and user names.

crackmapexec smb rebound.htb -u guest -p '' --rid-brute 10000

Usernames and groups
Usernames and groups

Now that we have usernames, we can guess popular passwords and test AS-REP Roasting.

AS-REP Roasting

The point of the AS-REP Roasting attack is that we send an anonymous request to the authentication server to provide a specific user with access to some service. To which the server has three different responses:

  • provides a ticket from where we will get the hash;
  • replies that this user does not have the flag set PreauthNotRequired;
  • says that such user is not in the Kerberos database.