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First time penetration test guidelines? : AskNetsec
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First time penetration test guidelines?
First time penetration test guidelines?
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So I've been working as tech support at this company about a year now. I'm trying to move up the chain a bit, and have been making strides. I've brought up the idea of doing a penetration test on my own network here to my boss, and she was very receptive and gave me the go ahead to plan it out, and to consult with a consultant we use for DevOps.
So I'm just now starting the planning stages of this pentest, and I'm kinda at a loss. I'm very new to the cyber security realm. The extent of my knowledge is that of 22 years of extensive computer use, I'm a senior in CS, and I've closed about 10-15 HacktheBox boxes, 1 of which was completely on my own. My main question at this point is how should I go about planning this pentest? What should I start with?
Here's my initial plan, though I just don't feel confident that it's enough, or that it follows industry standards.
Identify open ports/potentially vulnerable services
Identify web pages and injection opportunities
Attempt brute force on login points
So I think it's pretty obvious I'm not an experienced infosec expert. My job is fortunately enough giving me an opportunity to learn, and they understand that. I think my plan is pretty lacking in understanding after recon.
Detailed documentation, signed by your management, as high up as you can get, as to exactly what you can and cannot do.
That includes what you are and are not allowed to test, and when, and how. Don't even think about doing this until you have this.
Seconding this. Before you touch any targets, you need a signed scope agreement.
I'll for sure get signed documentation of this. At the very least it'll show I'm serious about it. Thank you!
You don't want to be doing a pen test. You want to do a vulnerability assessment. A pen test is completely different (and shouldn't be done by someone who doesn't know what they're doing - no offence)
1 - Get agreement on exactly what you are and aren't allowed to do. Your line manager being enthusiastic won't save you from the sack if you break something critical without having prior authorisation to do so
2 - Make sure you follow change management processes (if you have any). Working in an organisation that has a mature CM framework and ignoring it is a CV-generating event
3 - Use the free version of an off the shelf scanner like Nessus, make sure you aren't using destructive plugins, use non-credentialled scans to start with and work your way up to credentialled scans. Non-credentialled scans won't break anything that isn't already at serious risk of being broken (especially if its public-facing) but will at least find any gaping holes and demonstrate results before you move on to credentialled scans and potentially break something
4 - Scan out of hours. This de-risks things to an extent (less people on the network means less chance of serious effects in the middle of people working). You still need to pay attention though - in case something breaks and you're not aware of it until the morning
5 - Tell your monitoring and firewall/IPS teams. Nobody will thank you if they get paged at 2 AM because the IPS is lit up like a Christmas tree whilst Nessus blithely smashes away at your core servers :)
6 - Collate your results into a coherent report. Most of the 'cooler' vulnerability management stuff won't be available to you without a paid version of whatever tool you're using, so pull everything together into a spreadsheet and make some cool charts (most vulnerable servers, highest risk vulnerabilities, most widespread vulnerabilities across the estate etc)
7 - At some point, mention the need for a proper pen test, and suggest that you get involved in that. Recruit a pen test company and develop a framework for it in your organisation, get budget for it, and learn alongside whatever consultant they send
Number 5 made me smile, I have had a vuln scan do that to me.
Also for a basic vuln scan owasp zap is nice and easy to use as well. Runs in a container, so super easy to kick off and ignore.
OP might also want to assess their devsecops like code scanning and reporting.
There is nothing more wasteful whenever we conduct a pentest is to run into targets that haven't been through a basic vuln assessment.
I was going to PM this, but a few people messaged me and wanted to see it as well.
So I guess the first questions that need to be "What are you able to do?" I mean that from a legal perspective, not skills. What is your IP scope? Can you plug a random device into the network? Can you plug in USBs? Can you take over bluetooth devices? Will you have physical access to the server? Can you social engineer users? Can you sniff network traffic? Can you spoof network traffic? It seems like you are still on the "buy in" stage and need to keep pushing this up the chain, but definitely get the company lawyers involved. I would also have a lawyer do a quick look over what ever they come up with to protect your own interest. I have heard some horror stories of "my company said I could do a pentest but i brought down production and now they are suing me". Not trying to deter, just make sure you cover yourself. My normal setup is a laptop... no fancy hardware or anything. All you need is a laptop and time. So with all that out of the way I can give a little run down on how most of my pentests go (keep in mind my test are generally only 2 weeks so there is some down and dirty stuff):
Plug in, document your IP so you can prove what is you and what isn't. Literally everything will be blamed on you so you will need a way to prove you didn't take down or interrupt anything.
Ping the known IP ranges. Just ping the gateway to make sure you have connectivity. Some people will just say 192.168.0.0/16 for a scope because they want us to test everything. If you have the time, give the whole range a fast scan but also ask for the normal ranges the operate in so you can focus your efforts. There has yet to be an instance where we found something they company didn't know was there.
nmap everything. I start with a discovery scan then use those results to do a full port scan on any systems that are alive. It saves time and network traffic. I edit the ports on the discovery scan a little, but these are the string I normally use: https://github.com/killswitch-GUI/PenTesting-Scripts/blob/master/Nmap-Strings
Split out the web ports and give them to either EyeWitness or Aquatone . I prefer the output of EyeWitness but it will miss somethings Aquatone gets.
Feed all the hosts that were alive from the discover scan into Nessus, OpenVAS, or some other vulnerability scanner. Nesses will always be king, but if you cant get them to pay for it the others will work. It will just require more effort and the final report will not be as good.
Take a look through the vulnerability results. You are looking for low hanging fruit. Windows XP, Bluekeep/EternalBlue. You can come back and try the harder things later.
Take a look at the EyeWitness/Aquatone reports. Things you are looking for here are "key/critical" systems. Basically google "(name of web app) exploit" and "(name of web app) default password". Generally you are not going to get too far off of these things, but they can be used to show impact in your report. "Look at the data I was able to get to, now give me more money so we can get this fixed."
Everything above is your basic OSCP/HTB type methods. Below relies on Active Directory which should be used in pretty much every environment that has 25 or more employees.
8. Printers! Everyone talks about them but no one mentions what you do after you get on them or what you get from them. To get on them try default passwords or look for documents with username/passwords on shares. If you get in check if LDAP is configured. If it is swap out the serve with your IP and use responder to capture the credentials of the configured account.
9. Speaking of responder, let that baby run. It is a lot to explain but basically it takes advantage of deprecated protocols to have others send you their hashes. This is a pretty good guide: https://thor-sec.com/tutorial/responder_fun/
10. The guide above mentions smbexec... it is amazing and works with hashes or passwords. If you get a local administrator hash, spray it with this.
11. Bloodhound is gods (SpecterOps) gift to pentesters... and blue teamers... and anyone who works with AD. It more or less maps Active Direcroty relationships and help discovery misconfigurations and ways to attack them.
I am going to stop here... the last 4 things read quick, but they take a ton of practice and can easily break things. I think r/therealcruff hit the nail on the head... you want to do a vulnerability scan. Not a pentest. There is a reason people get paid a lot of money to do this.
no3. Phishing/Spoofing - you really want to follow advice below that you are certainly allowed this and whoever runs company are well aware of such things to begin, as this is issue with naive or not tech savy people that would rather benefit more from training how to spot it and having correct filtering gear in the first place.Also if theres no system in place to block any brute force attempts or weak password, not changed every month or so, it would benefit more from people being trained on the issue, so that leaves you with using existing exploits, which tbf if penetrated would be more then enough
that said ive just above basic networking and sys admin skills that are close to be outdated, as tech moves way to fast nowadays to keep tabs on, specially on the enterprise level.
All of these suggestions are great, however several actual frameworks for this exist. One of the most popular is PTES - PenTesting Execution Standard
A real pentest is nothing like HTB or the other site. Fell free to send me a PM and I can give you a quick and dirty pentest methodology for live networks.
I would ask management if they would be willing to help fund some pentest related certifications for you to take. eLearnsecurity, Offensive Security, and SANS all have some. These tests won't be that effective without the right knowledge. Most of what you are describing can be achieved with a vulnerability scanner like Qualys/Nessus, etc. A pentest is much more than that.
No notice, full discovery NESSUS scan from inside the network. JK, but I saw it happen once.
The other commenters are right. Need to be clear on what is permissible so you don’t wind up bringing your company down and getting fired.
Always wear a rubber the first time, even if they say they are on the pill.
I’d like to caution you that it’s considered highly unprofessional in our field (non-infosec professional computer stuff) to want to find vulnerabilities in your employer’s network. Even if your boss is for it, it’ll label you as a potential hacking hazard to management (hacking risk = potentially huge monetary loss risk). Keep in mind that in the not too dustant past the number 1 risk to networks was insider threats. An infosec company would potentially be a different story.
In all seriousness I would abandon the idea and never even suggest it again. If you want to pentest something maybe you could get permission from a local community college (especially if you’re a student). You could take some career relevant courses at the same time. Educational institutions care far far less about risking being hacked.
For what it’s worth you’ll occasionally stumble across potential security issues without looking.
I think if it was me (having worked as a penetration before), I would be trying to understand what the goal is. Is what you are doing going to provide business value? What objectives do you want to meet. I’d agreed with the comment about performing a vulnerability assessment instead, in order to get a baseline of the system patching etc. If you want it be a standard penetration test you may want to omit things like phishing as this may be stretching into the realms of red-teaming (but again, depends on your goal). In addition, be careful with brute forcing, as penetration tests don’t normally contain any destructive testing, an aggressive brute force may even dos the application.
Please share the information here rather than making it private, so that other readers may benefit.
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