Reel2 - HackTheBox Writeup (10.10.10.210)

Posted on Sat, Mar 20, 2021 Hard Windows Password Spraying Outlook Web App Powershell JEA
Hard-difficulty Windows box with a focus on password spraying attacks and NetNTLMv2 hash phishing on Outlook. Privilege escalation by abusing an insecure Powershell JEA cmdlet with symbolic links, while bypassing PS constrained language mode.

Recon

Enumeration

Port 80 Enumeration

Port 443 Enumeration

Port 8080 Enumeration

Exploitation

OWA Password Spraying

NetNTLMv2 hash stealing using Outlook

Privilege Escalation

Persistence

Resources

  1. https://github.com/munafio/wallstant
  2. https://book.hacktricks.xyz/windows/active-directory-methodology/password-spraying#outlook-web-access
  3. https://www.ired.team/offensive-security/initial-access/netntlmv2-hash-stealing-using-outlook
  4. https://blog.rapid7.com/2020/04/06/phishing-for-system-on-microsoft-exchange-cve-2020-0688/
  5. https://docs.microsoft.com/en-us/powershell/module/microsoft.powershell.core/enter-pssession?view=powershell-7.1
  6. https://blog.netspi.com/15-ways-to-bypass-the-powershell-execution-policy/
  7. https://www.ired.team/offensive-security/code-execution/powershell-constrained-language-mode-bypass
  8. https://winaero.com/create-symbolic-link-windows-10-powershell/