FLAG1


FLAG13


FLAG21


FLAG31


Enumeration

PORT     STATE SERVICE       VERSION
22/tcp   open  ssh           OpenSSH for_Windows_7.9 (protocol 2.0)
| ssh-hostkey: 
|   2048 36:a3:b5:c4:d1:e9:7f:ba:49:54:4a:e3:1c:6a:56:35 (RSA)
|   256 66:a2:45:35:de:ec:8a:ef:cf:e9:69:cd:d4:75:69:2e (ECDSA)
|_  256 50:1c:9e:fa:ad:65:3d:f8:a0:57:9b:ca:99:f0:47:90 (ED25519)
80/tcp   open  http          Microsoft IIS httpd 10.0
|_http-server-header: Microsoft-IIS/10.0
|_http-title: IIS Windows Server
| http-methods: 
|_  Potentially risky methods: TRACE
135/tcp  open  msrpc         Microsoft Windows RPC
139/tcp  open  netbios-ssn   Microsoft Windows netbios-ssn
445/tcp  open  microsoft-ds  Microsoft Windows Server 2008 R2 - 2012 microsoft-ds
3389/tcp open  ms-wbt-server Microsoft Terminal Services
| ssl-cert: Subject: commonName=IamGroot.pwntilldawn.ctf
| Not valid before: 2022-09-16T12:52:10
|_Not valid after:  2023-03-18T12:52:10
| rdp-ntlm-info: 
|   Target_Name: IAMGROOT
|   NetBIOS_Domain_Name: IAMGROOT
|   NetBIOS_Computer_Name: IAMGROOT
|   DNS_Domain_Name: IamGroot.pwntilldawn.ctf
|   DNS_Computer_Name: IamGroot.pwntilldawn.ctf
|   Product_Version: 10.0.14393
|_  System_Time: 2022-09-17T14:45:37+00:00
|_ssl-date: 2022-09-17T14:46:16+00:00; +33m56s from scanner time.
Service Info: OSs: Windows, Windows Server 2008 R2 - 2012; CPE: cpe:/o:microsoft:windows

Host script results:
| smb-security-mode: 
|   account_used: guest
|   authentication_level: user
|   challenge_response: supported
|_  message_signing: disabled (dangerous, but default)
| smb2-security-mode: 
|   3.1.1: 
|_    Message signing enabled but not required
| smb2-time: 
|   date: 2022-09-17T14:45:39
|_  start_date: 2021-06-24T21:27:58
|_clock-skew: mean: 33m56s, deviation: 0s, median: 33m55s

Enumerating Port 22 - OpenSSH for_Windows_7.9

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searchsploit -m 45233

Create Python2 Virtualenv before running the script

virtualenv -p python2 venv
source venv/bin/activate

Enumerating Port 80

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┌──(kali㉿kali)-[~]
└─$ gobuster dir -u <http://10.150.150.135/> -w /usr/share/wordlists/dirb/common.txt -q -t 200
/Admin                (Status: 301) [Size: 151] [--> <http://10.150.150.135/Admin/>]
/admin                (Status: 301) [Size: 151] [--> <http://10.150.150.135/admin/>]
/ADMIN                (Status: 301) [Size: 151] [--> <http://10.150.150.135/ADMIN/>]

After waiting for a while we have this prompt but I am not sure how was it triggered

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