Intercept (Chain)

This is not a writeup, just my notes about the machine.

Operating System: Microsoft Windows Server 2022 Standard

Chain: True (2 Machines)

Credentials

Username
Password
Method
Scope

kathryn.spencer

Chocolate1

Capture NTLMv2

Domain User

Simon.Bowen

b0OI_fHO859+Aw

NTLM Relay attack

Domain User

✅ Valid Usernames

🔑 Passwords list

Information Gathering

Nmap Scan

Service Enumeration

10.10.202.53

DNS

  • Not vulnerable to DNS Zone Transfer AXFR

SMB (enum4linux-ng)

  • Domain SID: S-1-5-21-3031021547-1480128195-3014128932

  • Root/Parent Domain Controller

  • Domain: intercept.vl

  • NetBIOS: DC01

  • FQDN: DC01.intercept.vl

  • Server allows null session authentication

Kerberos (Kerbrute)

  • statistically-likely-usernames/john.smith.txt returned valid usernames

10.10.202.54

SMB (Enum4linux-ng)

  • NetBIOS: WS01

  • Domain: intercept.vl

  • FQDN: WS01.intercept.vl

  • Server allows null session authentication

  • Server allows guest user authentication. (Useful)

  • Available Folder for guest authentication:

    • dev - READ,WRITE

    • Users - READ

Compromising domain user

Finding a valid usernames

  1. They was not configured with UF_DONT_REQUIRE_PREAUTH set

  2. Not username as password

  3. Not empty password

Finding interesting files

Crafting malicious files to capture NTLMv2 hashes

Uploading the files into dev folder

Capturing Kathryn.Spencer's NTLMv2 hash

Cracking

Credentials found: KATHRYN.SPENCER:Chocolate1

Default enumeration with valid credentials:

  • Retrieved valid usernames

  • Not bruteforce/password spraying successfully (empty,username as password)

  • Not asreproast users

  • Not kerberoast users

  • Not ADCS vulnerable templates

    • Found PKI Enrollment Server: DC01.intercept.vl

    • Found CN: intercept-DC01-CA

  • kathryn.spencer possesses MachineAccountQuota: 10 .

  • Coerce_plus by netexec

    • VULNERABLE, DFSCoerce

    • VULNERABLE, PetitPotam

    • VULNERABLE, PrinterBug

    • VULNERABLE, MSEven

Discovering a exploitable LDAP misconfiguration

  • LDAP Signing NOT Enforced!

  • LDAPS Channel Binding is set to "NEVER"

Discovering a WebClient Service available

WebClient Service enabled on: 10.10.141.166

circle-info

WebClient service can be indirectly abused by attackers to coerce authentications. This technique needs to be combined with other coercion techniques (e.g. PetitPotam, PrinterBug), or multicast poisoning, to act as a booster for these techniques. It allows attackers to elicit authentications made over HTTP instead of SMB, hence heightening NTLM relay capabilities.

Abusing NTLM Relay Attack

To successfully carry out this attack, the environment must have the following misconfigurations:

  • LDAP Signing is NOT enforced

  • LDAPS Channel Binding is set to "NEVER"

  • MachineAccountQuota > 0 (allows low-privileged users to create computer accounts)

  • PetitPotam vulnerability is present

  • Valid NetBIOS name resolution via Responder

  • Intranet zone conditions has to be meet.

    • Which means add our Computer to the domain using the NetBIOS provided by Responder

Running responder to generate Netbios

/usr/share/responder/Responder.conf > SMB = Off and HTTP = Off

Adding our machine to the domain’s DNS records

Coercing Authentication

Output

Abusing Resource Based Constrained Delegation

Requesting Ticket Granting Ticket using S4U

Dumping SAM database and LSA Secrets

Credentials found: Simon.Bowen:b0OI_fHO859+Aw

Compromise Domain Controller

During the enumeration phase, it was discovered that the user Simon.Bowen is a member of the HelpDesk domain group. This group has GenericAll permissions over the CA-Managers group, which manages the enterprise Certificate Authority (CA) intercept-DC01-CA.

This attack exploits ESC7, where over-permissioned users/groups are able to reconfigure the Certificate Authority. By enabling SAN injection and creating malicious certificates, the attacker escalates to Domain Admin privileges without triggering standard authentication alerts.

Adding simon.bowen to ca-managers domain group

Enabling SubCA Template

Adding officer on intercept-DC01-CA

Requesting Administrator certificate using Subject Alternative Name (SAN)

Although initial enrollment failed due to template restrictions, the request was submitted and manually approved via:

Approving administrator certificate

Retrieving Administrator certificate

Requesting Administrator's Ticket Granting Ticket

Performing DCSync Attack

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