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The Mercury

The Mercury

Passionate about offensive cyber security, Sharpening my skills by playing CTF machines and challenges.

Checkpoint | Hackthebox | Windows & AD | Medium

5 min readSep 30, 2026

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Given credentials ==> alex.turner:Checkpoint2024!

Stage1: Recon And Enumeration

  • Once i got the output of Nmap, i found that’s an Active Directory environment and there’s SMB Share.
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  • So i checked the permissions of user “alex.turner” on this SMB share, And i found that i have READ permission on some shares and got nothing from them.
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  • And for discovering the environment, I enumerated the users of this Active Directory environment, I found some users and only one service account “svc_deploy” and three administrators’ accounts.
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  • I checked the permissions of “alex.turner” on Active Directory Groups, … , And i found that i have “DACL: WRITE” permission on “CN=Deleted Objects” and “Permission: WRITE” on deleted object “Mark Davies” (that’s our target account).
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  • Once i have these permissions i can restore the deleted user and use his permission on the environment.
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  • Now i have Active Directory users and deleted users, so i tried “Password Spraying” attack on these users with password of “alex.turner” and i found that it matches with restored user “Mark”.
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Stage2: Finding The First Foothold

  • Once i got another account’s credentials “Victim Mark:Checkpoint2024!”, I checked his permission on SMB Shares and I’ve got that i have READ, WRITE permission on “DevDrop” share which’s holds VSCode vsix extension.
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Press enter or click to view image in full size
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  • I’ve successfully got a shell with “ryan.brooks” user, and I’ve got User Flag.
  • I’ve got data collection via sharphound and map the Active Directory environment.

Stage3: Environment Analysis

  • I’ve got data collection via SharpHound.exe for mapping Active Directory Environment.
  • After that i checked “BadSuccessor” (one of the most popular vulnerabilites on windows server recently) and i got two users can perform this attack.
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  • From “BloodHound” map, there’s relationship with “ryan.brooks” and “svc_deploy” account and that’s a user responsible for backups (Maybe have and access on ‘VMBackups’ SMB share) and “ryan.brooks” have needed permission on OU=DMSAHolder
  • So i’ll perform “BadSuccessor” attack with “ryan.brooks” user.
  • NOTE: you need to search about dMSA and BadSuccessor, How it works to understand this part.
  1. I got TGT of “ryan.brooks” by Rubeus.exe
Rubeus.exe tgtdeleg /nowrap
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2. I took this base64 encoded TGT and decrypted it then converted to ccache ticket, Now i have “ryan.brooks” credentials i can authenticate with to perform “BadSuccessor” attack.

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Press enter or click to view image in full size

3. Then i created malicious dMSA account using ‘badSuccessor’ module in bloodyAD and i got NT Hash of that account.

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4. I took NT Hash and authenticate with “svc_deploy” username and evil-winrm.

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5. I’ve successfully got “svc_deploy” shell and i have READ permission on “VMBackups” SMB share.

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Stage4: Privilege Escalation

  • After discovering ‘VMBackups’ SMB share, I found vmware memory snapshot of the windows machine, That’s very interesting cause it may have plaintext credentials and NT Hashes.
  • I uploaded vmkatz.exe on windows machine to analyze the snapshot, And i’ve successfully got Administrator’s NT Hash.

VMkatz: https://github.com/nikaiw/VMkatz/releases/tag/v1.4.1

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Stage5: Root Flag

  • I took Administrator’s NT Hash and authenticate with evil-winrm, And i got flag on ‘max.palmer’ user.
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Lessons Learned

  • Active Directory permissions’ exploitation.
  • Getting foothold via VSCode.
  • Practicing on BadSuccessor vulnerability.
  • Memory forensics.
  • Don’t miss the backups.

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The Mercury
The Mercury

Written by The Mercury

Passionate about offensive cyber security, Sharpening my skills by playing CTF machines and challenges.