Recommended Boot2Root Machines

After some research I created this personal “to do” list of recommended / famous / must-solve Boot2Root machines from Vulnhub and HTB focused mainly on OSCP preparation.

The list is NOT only about machines similar to OSCP. It also includes machines that are way easier or harder than OSCP but are worth solving as and you will definitely learn something new from each one.
It is recommended to solve at least 50 machines from Vulnhub & HTB before you dive for your OSCP exam.

While solving them don’t forget to avoid using Automatic exploitation tools (e.g. db_autopwn, browser_autopwn, SQLmap, SQLninja etc.) as the exam forbids them. (https://support.offensive-security.com/oscp-exam-guide/)

Also try to avoid Metasploit as you are allowed to use it only on one machine in the exam. So you should better avoid it while solving machines.

Don’t forget to check these two awesome courses focused specifically on OSCP prep.
Cybrary OSCP Course
INE OSCP Security Technology Course

Also check the following links I have collected with useful OSCP related stuff.
OSCP-Survival-Guide
TJnull’s Preparation Guide for PWK/OSCP
Github OSCP Prep
OSCP survival guide
Github OSCP Prep 2
Total OSCP guide
OSCP Basic notes
Newbie to OSCP
How to Pass OSCP Like Boss.
Passing OSCP – scund00r
OSCP useful resources and tools
OSCP Human Guide
How to pass the OSCP
A curated list of awesome OSCP resources
A reconnaissance tool made for the OSCP labs
HackTheBox OSCP-like Machines

PS: HTB machines are categorized by platform Windows/Linux and are sorted by difficulty. OSCP-like machines are reported by users to usually be bellow 5 in the HTB difficulty scale.

Vulnhub Linux Machines

NameDifficulty (My rating)CompletedShort Notes (No spoilers)Recommended writeup
DeRKnStiNK 1Easy - BeginnerYESCTFish, Flags, Webhttps://emaragkos.gr/vulnhub-writeups/vulnhub-derknstink-1-walkthrough/
RICKdiculouslyEasy 1Easy - BeginnerYESReally CTFish, Flags, Enumeration, Web, RCE, Bruteforce, Stego, Fun to solve
https://emaragkos.gr/vulnhub-writeups/rickdiculouslyeasy-1-vulnhub-walkthrough/
covfefe: 1Easy - BeginnerYESCTFish, Flags, Enumeration, Bruteforce, Interesting noob friendly intro to BOFhttps://emaragkos.gr/vulnhub-writeups/vulnhub-covfefe-walkthrough/
Dina: 1.0.1Easy - BeginnerYESWeb, Not really originalhttps://emaragkos.gr/vulnhub-writeups/dina-101-vulnhub-walkthrough/
LazySysAdmin 1.0Easy - BeginnerYESCTFish, Flags, Web, SMBhttps://emaragkos.gr/vulnhub-writeups/lazysysadmin-1-0-vulnhub-walkthrough/
FristiLeaks: 1.3Easy - BeginnerYESCTFish, Enumeration, Web, Cryptography, Interesting PrivEschttps://5h4d0wb0y.github.io/2017-04-10-fristileaks/
HackInOS: 1IntermediateYESOSCP-prep, Awesome machine, Original, Web, Coding, Fuzzing, Bruteforce, Interesting PrivEsc, Pivotinghttps://ethicalhackers.club/hackinos-level-1-vulnhub-complete-walkthrough-guide/
JIS-CTFExtremely EasyYESNot really original, Poor challenges, Bad English, CTFish, Flags, Web, Enumerationhttps://medium.com/@w3rallmachines/jis-ctf-vulnupload-vulnhub-walkthrough-b33ba57b2be0
Lord Of The Root: 1.0.1Intermediate - AdvancedNO (I tried, not ready yet)OSCP-prep, Awesome machine, Original, Enumeration, Port Knocking, Web, Multiple ways for PrivESC with Advanced ASLR BOF or MYSQLhttps://barnyserver.com/ctf/2018/03/ctf-lord-of-the-root-1-0-1/
Mr-Robot: 1Easy - IntermediateYESCTFish, Flags, Enumeration, Bruteforce, Interesting PrivEschttps://nikolaskama.me/mr-robot-1-writeup/
SkyTower: 1Easy - IntermediateYESCTFish, Enumeration, Web, SQLi filtering, Proxyhttps://highon.coffee/blog/skytower-walkthrough/
The Necromancer: 1
Sokar: 1
SolidState: 1
Stapler: 1Easy - IntermediateYESCTFish, Flags, Enumeration, Bruteforce, Web, Rabbit Holeshttps://www.mrb3n.com/?p=81
Tommy Boy: 1
HackLAB: VulnixIntermediate - AdvancedNO (I tried, not ready yet)Focuced on enumeration, Many ports, Interesting and more advanced enumeration than most of the machines, Requires solid understanding of Linuxhttps://www.rebootuser.com/?p=988
zico2: 1
WinterMute: 1
Pegasus: 1IntermediateNO (I tried, not ready yet)OSCP-prep, Original, Web, Enumeration, BOFhttps://g0blin.co.uk/pegasus-vulnhub-writeup/
Homeless: 1
pWnOS: 2.0 (Pre-Release)
/dev/random: scream
W1R3S: 1.0.1
pluck: 1
OwlNest: 1.0.2
GoldenEye: 1IntermediateYESOSCP-prep, Enumeration, Bruteforce, Really CTFish, Interesting WebApp Exploitation, Typical PrivEsc with a few catches.http://www.anonhack.in/2018/07/goldeneye-1-walkthrough-vulnhub-vulnerable-machine/
g0rmint: 1
W34kn3ss: 1
digitalworld.local: MERCY v2
digitalworld.local: BRAVERY
Toppo: 1
Bob: 1.0.1
NullByte: 1
Lin.Security: 1
unknowndevice64: 1
Brainpan: 1NO (I tried, not ready yet)
Brainpan: 2
Brainpan: 3
Breach: 1
Breach: 2.1
Breach: 3.0.1
Hackademic: RTB1Easy - BeginnerYESRealistic, Outdated software, Enumeration, Web, Common Priv Eschttps://chousensha.github.io/blog/2016/07/18/pentest-lab-hackademic-rtb1/
Hackademic: RTB2
Kioptrix: Level 1 (#1)Easy - BeginnerYESMeh, not really originalhttps://emaragkos.gr/vulnhub-writeups/kioptrix-level-1-vulnhub-walkthrough/
Kioptrix: Level 1.1 (#2)Easy - BeginnerYESWeb, SQLi, RCEhttps://www.abatchy.com/2016/12/kioptrix-2-walkthrough-vulnhub
Kioptrix: Level 1.2 (#3)
Kioptrix: Level 1.3 (#4)
Kioptrix: 2014 (#5)
SickOs: 1.1Easy - BeginnerYESCreator mentions that "This vm is very similar to labs I faced in OSCP." Personally I found it pretty easy compared to other machines that mention the same thing. CTFish, Enumeration, Web, Not really original except the proxy thing (no spoilers). https://www.youtube.com/watch?v=kkHYPRmS4kw
SickOs: 1.2
billu: b0x
billu: b0x 2
Tr0ll: 1Easy - BeginnerYESCreator mentions that "Tr0ll was inspired by the constant trolling of the machines within the OSCP labs. " Personally I found it pretty easy compared to other machines that claim that are OSCP-like. CTFish, Enumeration, Web, Trolling, Basic Priv Eschttps://www.sw1tch.net/2014/08/16/walkthrough-for-tr0ll-1/
Tr0ll: 2

Vulnhub Windows Machines

NameDifficulty (My rating)CompletedShort notes (No Spoilers)Recommended writeup
Bobby: 1
/dev/random: scream

 IppSecs’ videos categorized by OS and difficulty! 

 Search IppSecs’ videos context by text! 

HackTheBox Linux Machines

NameDifficulty (HTB rating)CompletedShort Notes (No spoilers)Skills RequiredSkills LearnedRecommended writeup
Lame2.7YESLame is a beginner level machine, requiring only one exploit to obtain root access. It was the first
machine published on Hack The Box and was often the first machine for new users prior to its
retirement.
● Basic knowledge of Linux
● Enumerating ports and services
● Identifying vulnerable services
● Exploiting Samba
https://www.youtube.com/watch?v=Ru8YxARNS7M
Bashed3.5YESBashed is a fairly easy machine which focuses mainly on fuzzing and locating important files. As
basic access to the crontab is restricted.
● Basic knowledge of Linux
● Enumerating ports and services
● Basic web fuzzing techniques
● Locating recently modified files
https://www.youtube.com/watch?v=2DqdPcbYcy8
Nibbles3.7YESNibbles is a fairly simple machine, however with the inclusion of a login blacklist, it is a fair bit
more challenging to find valid credentials. Luckily, a username can be enumerated and guessing
the correct password does not take long for most.
● Basic knowledge of Linux
● Basic understanding of web
● Enumerating web applications
● Guessing probable passwords
enumeration techniques
● Bypassing login rate limiting
● Exploiting NOPASSWD
https://www.youtube.com/watch?v=s_0GcRGv6Ds
Mirai3.8YESMirai demonstrates one of the fastest-growing attack vectors in modern times; improperly
configured IoT devices. This attack vector is constantly on the rise as more and more IoT devices
are being created and deployed around the globe, and is actively being exploited by a wide
variety of botnets. Internal IoT devices are also being used for long-term persistence by malicious
actors.
● Intermediate knowledge of Linux
● Enumerating ports and services
● Basic knowledge of the Mirai botnet
● Identifying an IoT device
● Forensic file recovery
https://www.youtube.com/watch?v=SRmvRGUuuno
Shocker3.8YESShocker, while fairly simple overall, demonstrates the severity of the renowned Shellshock
exploit, which affected millions of public-facing servers.
● Basic knowledge of Linux
● Exploiting NOPASSWD
● Exploiting shellshock
● Enumerating ports and services
https://www.youtube.com/watch?v=IBlTdguhgfY
Beep3.9YESBeep has a very large list of running services, which can make it a bit challenging to find the
correct entry method. This machine can be overwhelming for some as there are many potential
attack vectors. Luckily, there are several methods available for gaining access.
● Basic knowledge of Linux
● Enumerating ports and services
● Web-based fuzzing
● Identifying known exploits
● Exploiting local file inclusion
vulnerabilities
https://www.youtube.com/watch?v=XJmBpOd__N8
Sense3.9
Poison3.9
Sunday4.1
Valentine4.2
Solidstate4.3
Popcorn4.3
Cronos4.4
Haircut4.7
Nineveh5.4
Node6.2
TartarSauce6.2
Brainfuck6.8
Kotarak6.9

HackTheBox Windows Machines

NameDifficulty (HTB rating)CompletedShort Notes (No spoilers)Skills RequiredSkills LearnedRecommended writeup
Legacy2.4YESLegacy is a fairly straightforward beginner-level machine which demonstrates the potential
security risks of SMB on Windows. Great place to start even if this is your first machine ever. As the name says is about a Legacy OS and a good old rockstar of exploits, the infamous ms08_067_netapi.
● Basic knowledge of Windows
● Enumerating ports and services
● Identifying vulnerable services
● Exploiting SMB
https://www.youtube.com/watch?v=wOeYLZazLGI
Blue2.5YESA really simple machine that shows the power of ms17_010_eternalblue. Another rockstar exploit that you should definitely know how to handle. Nothing fancy here but still a really nice machine for beginners. ● Basic knowledge of Windows
● Enumerating ports and services
● Identifying Windows targets using SMB
● Exploit modification (optional)
https://www.youtube.com/watch?v=YRsfX6DW10E
Jerry2.9YESAlthough Jerry is one of the easier machines on Hack The Box, it is realistic as Apache Tomcat is
often found exposed and configured with common or weak credentials. Simple machine, Basic enumeration, Introduction to msfvenom, Easy privsec
● Basic Python/Ruby etc. or familiarity
with web brute force attack tools
● Basic script debugging
● Custom war file payload creation
● SILENTTRINITY post-exploitation
framework installation and usage
(courtesy of ​ IppSec Jerry video)
https://www.youtube.com/watch?v=PJeBIey8gc4
Granny3.6YESGranny, while similar to Grandpa, can be exploited using several different methods. The intended
method of solving this machine is the widely-known Webdav upload vulnerability.
● Basic knowledge of Windows
● Enumerating ports and services
● Identifying known vulnerabilities
● Identifying stable processes
● Basic Windows privilege escalation
techniques
https://www.youtube.com/watch?v=ZfPVGJGkORQ
Grandpa3.7YESGrandpa is one of the simpler machines on Hack The Box, however it covers the widely-exploited
CVE-2017-7269. This vulnerability is trivial to exploit and granted immediate access to thousands
of IIS servers around the globe when it became public knowledge.
● Basic knowledge of Windows
● Enumerating ports and services
● Identifying known vulnerabilities
● Identifying stable processes
● Basic Windows privilege escalation
techniques
https://www.youtube.com/watch?v=ZfPVGJGkORQ
Optimum3.7YESOptimum is a beginner-level machine which mainly focuses on enumeration of services with
known exploits. Both exploits are easy to obtain and have associated Metasploit modules,
making this machine fairly simple to complete.
● Basic knowledge of Windows
● Enumerating ports and services
● Identifying vulnerable services
● Identifying known exploits
● Basic Windows privilege escalation
techniques
https://www.youtube.com/watch?v=kWTnVBIpNsE
Devel3.7YESDevel, while relatively simple, demonstrates the security risks associated with some default
program configurations. It is a beginner-level machine which can be completed using publicly
available exploits.
● Basic knowledge of Windows
● Enumerating ports and services
● Identifying vulnerable services
● Exploiting weak credentials
● Basic Windows privilege escalation
techniques
https://www.youtube.com/watch?v=2LNyAbroZUk
Chatterbox4.0
Bounty4.8
Bastard5.0
Jeeves5.0
Silo5.2
Reel6.1
Bart6.3
Tally6.5