Jeeves
OS: Windows, Difficulty: Medium, IP: 10.10.10.63
Initial Enumeration
# Nmap 7.70 scan initiated Mon Jul 22 01:27:35 2019 as: nmap -sV -sC -O -A -oN O-Detailed -p 80,135,445,50000 10.10.10.63
Nmap scan report for 10.10.10.63
Host is up (0.34s latency).
PORT STATE SERVICE VERSION
80/tcp open http Microsoft IIS httpd 10.0
| http-methods:
|_ Potentially risky methods: TRACE
|_http-server-header: Microsoft-IIS/10.0
|_http-title: Ask Jeeves
135/tcp open msrpc Microsoft Windows RPC
445/tcp open microsoft-ds Microsoft Windows 7 - 10 microsoft-ds (workgroup: WORKGROUP)
50000/tcp open http Jetty 9.4.z-SNAPSHOT
|_http-server-header: Jetty(9.4.z-SNAPSHOT)
|_http-title: Error 404 Not Found
Warning: OSScan results may be unreliable because we could not find at least 1 open and 1 closed port
Device type: general purpose
Running (JUST GUESSING): Microsoft Windows 2008|10 (88%), FreeBSD 6.X (85%)
OS CPE: cpe:/o:microsoft:windows_server_2008:r2 cpe:/o:microsoft:windows_10 cpe:/o:freebsd:freebsd:6.2
Aggressive OS guesses: Microsoft Windows Server 2008 R2 (88%), Microsoft Windows 10 1511 - 1607 (85%), FreeBSD 6.2-RELEASE (85%)
No exact OS matches for host (test conditions non-ideal).
Network Distance: 2 hops
Service Info: Host: JEEVES; OS: Windows; CPE: cpe:/o:microsoft:windows
Host script results:
|_clock-skew: mean: 4h53m14s, deviation: 0s, median: 4h53m14s
| smb-security-mode:
| authentication_level: user
| challenge_response: supported
|_ message_signing: disabled (dangerous, but default)
| smb2-security-mode:
| 2.02:
|_ Message signing enabled but not required
| smb2-time:
| date: 2019-07-22 06:21:13
|_ start_date: 2019-07-22 06:08:01
TRACEROUTE (using port 80/tcp)
HOP RTT ADDRESS
1 234.36 ms 10.10.14.1
2 411.09 ms 10.10.10.63
OS and Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
# Nmap done at Mon Jul 22 01:28:34 2019 -- 1 IP address (1 host up) scanned in 59.36 secondsSMB ports, guest account disabled, anonymous login disabled. No luck. Gobuster for port 80, nothing, however for port 50000 there was something interesting.


However I upgrade the commands to the following to have better output
Executed the command above to get a wget.ps1 file that downloads my meterpreter shell into the system and executes it, this got me user shell on MSF Console.
User Own
Root Own
Got system shell, however there was no root.txt file in the Administrator/Desktop folder, as there is supposed to be however there was a text stating the following.
After investing 3-4 Hours figuring out, the following thing worked.
Learning Outcome
Always enumerate for alternate data sources of files as well as for hidden files.
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