Red Team Penetration Testing - Purple Team Penetration Testing

March 30, 2021

Episode #22 - Penetration Testing: What You Need to Know (Part 3)

This week, the guys continue their penetration testing discussion, covering the following common questions:

How often should your organization conduct a penetration test?
What's the right approach, red team penetration testing or purple team penetration testing?
What should you see in your penetration test reports?

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welcome to the cyber ants podcast this is your co-host

zach fuller joined by mike rotondo and lauro chavez and today we are continuing our

mini-series about penetration testing and have some great topics and considerations to cover

but before that why don't you kick us off with the news in the usual fashion mike hello

everybody and uh welcome to the news today first we're going to start out with russian

hacker pleads guilty to planting malware in tesla gigafactory apparently um scott was an employee

uh working on a tesla gigafactory it was offered a million dollars a bitcoin if they facilitated an

attack also he planned to carry out a distributed denial of service attack which would have diverted

the company's attention paving way for another attack watch your employees firm search to patches

attackers exploit critical f5 bugs uh there's a new cbe out there 20 21-229-86 it's a flaw

in rest-based eye control management interface which could allow for authentication bypass and

remote code execution it's at a rating of 9.8 popular remote lesson monitoring program can be

exploited to attack student pcs this is kind of disconcerting there's a new teaching tool called

net up vision pro which contained vulnerabilities it could be exploited basically you weren't even

you were not able to encrypt the network traffic and students would automatically start sending

screenshots to the teacher whether they knew it or expected to do so or not um we've got another

disgruntled employee an admin with an axe to grind sent to prison for wiping microsoft user accounts

uh this is basically everybody's worst nightmare 32 year old employee was fired went back to india

while he was outside the us he deleted 80 percent of the employers microsoft 365 accounts needless

to say company ground to a halt for a while um and he's going to jail for two years so there's that

back in the wayback machine everybody remember melissa the first big virus

managed to disrupt hundreds of networks including those of microsoft this was back in march of 1999

at least a hundred thousand workplace computers were affected understanding remote security remote

work security that's the world we're in today and really what it comes down to it's an interesting

little article uh but it's basically a breach even one employee's laptop is bad but it breached the

entire company's infrastructure and potentially everyone connected to it is much worse so

what's happening is companies find it more difficult to keep remote employees secure than to

prevent malware on a remote laptop from infecting infrastructure this is added because i simply like

saying purple fox root kit purple fox root kit can now spread itself to other windows computers

there's 90 thousand incidents that have been spotted in the wild through 2020 in the

beginning of 2021 uh it's got a novel spreading technique uses using indiscriminate port scanning

and exploitation of exposed smb services with weak passwords and hashes how many times you get those

internal scans you go oh it's just smb we're not going to worry about fixing that well guess what

purple fox root kit it's looking for you um phishing leads to breach a california state

controller this one i kind of laugh at because i mean it's serious but

basically what happened is there was a phishing attack that exploited wound up exploiting uh the

state controller's office of california fishers had access for more than 24 hours the intruders

used that time to steal social security numbers and sensitive files of thousands of state workers

on the send targeted phishing messages to at least nine thousand other workers in their contacts

the reason i kind of laugh is that is because in october 2020 someone in their great wisdom

at the california department technology decided to exclude managers and supervisors from being fish

tested uh using dynamic testing they had to know everything about it so basically they they gutted

their testing sys gutted their testing and wound up getting hacked because of it uh black kingdom

ransomware hunting unpatched microsoft exchange servers yep that's still happening there's another

another attack out there they're trying to exploit anybody that has not patched and if you

haven't patched yet i'm sorry two-thirds of the large firms attacked as kobe 19 hamper security

from the 27 percent of businesses experience attacks at least once a week with phishing at

83 an impersonation 27 most common a fifth 21 of those reporting attacks end up losing money data

or other assets as a result and 35 reported other negative consequences such as business instruction

or a loss of staff productivity a critical cisco jabber bug could let attackers hack remote systems

it allows you to execute arbitrary programs on the undulating underlying operating system

cause the ddos intercept protected traffic or access sensitive information and with that let's

go ahead and end out the headlines go ahead lauro purple fox root kit i like that that's kind of

cool yeah the clever clever names yeah yeah like he's like like you said if you haven't patched

already time to give up i.t in the exploit world this week we really only have one to be of concern

about um and that's with an online ide it's an integrated development environment basically

a sas platform that allows you development capabilities it's called cody dad and there

was a remote code execution that was provided via python to um as a module for metasploit fantastic

all you need to do is get a demo account and you need to be authenticated for the rce to work

but that's super easy to get through the through the application so this has been

communicated to cody dad and they've hopefully been remediating this but just as a cautionary

entail to everybody be careful of be wary of using online platforms to do your development

on okay they're not they're not all you know really really doing their security testing

or penetration testing which you know it you know brings us brings us to the circle of conversation

today but that's that's really i think um all to be aware of this week for exploits in the wild

that are going to be weaponized in metasploit pro or metallic framework if you uh like the

free version well as we continue our discussion about penetration testing our our goal through

these podcasts of course is to answer a lot of common questions that come up that we hear

about these various topics and so today we want to dive into a few more topics about penetration

testing and just address various approaches and reporting and such but before we dive into that

how often do you think somebody should get a penetration test that's that's a

very very valid concern that a lot of people have and and what would you advise them

when they're wondering what what frequency is appropriate for our organization great entryway

i think for and certainly something we hear a lot there's a couple ways to answer this question

so if you're going to ask somebody who is doing this for a living they're going to

tell you the more frequent the better there are products out there that will actually let you do

round-the-clock live campaign testing in your own networks um and so you know there you can

be as proactive as you want to what i will say is that annually is probably just now scratching the

bare minimum and that that seems to be what the theme was for a long time because um traditionally

these these were more complicated and and you know there was a lot more convolutedness in what was

occurred and there was a lot less canned reports back in the day so they felt once once a week or

once a year was was adequate i think in a lot of the governance frameworks nist and you know

pci and things like that that would require an annual pen test and that that's probably great

so you know i guess it comes back to what's your intent is your intent to check a box then once a

year is probably frequent enough but if you're concerned and you're not sleeping well at night

because you know you've got development staff that are making changes or you've got infrastructure

changes that are going on or you're migrating things from an on-prem environment to the cloud

and there's there's changes happening that aren't giving you that high confidence of a low-risk

environment that you may be used to having and so that may something like that may cause you to to

ramp the frequency in your pin testing um i think quarterly is is really going to be the standard um

what what frameworks like pci will throw in some i call it magician's language to kind

of allow you to you know essentially draw your own i say you know draw your own firing squad so

they'll say things like upon significant changes right so pin testing should occur

annually and upon significant changes here's the thing is that pci and we don't know about four yet

but they won't they won't necessarily uh define what a significant change is nor can they in your

environment right that's up for your business to decide so most businesses we say they choose not

to define it and therefore they're not held to any accountability of any kind now if they define a

significant change as like you know you know an updated jquery library in your web application

for example that would denote a pin test right under the guise of the pci language

and so again you draw your firing squad so you can you can write yourself into a

really really expensive around-the-clock penetration testing routine however while that

business people may look at that as costly all your security governance and financial

risk people are going to look at that as um proactive right we're we're we we have now a

very current risk snapshot of the environment and all the changes that are happening if you're

just trying to check the block and you know you don't really care about the business that you're

serving then maybe annually is going to be your number to go for and if you're part of an i.t

department and you've got a lot of changes going on and you really care about understanding the

the protective posture of the organization at any given time then you know you may want to

at least do quarterly maybe monthly maybe you should define those significant changes and

what they mean to you if you're if you're bound by pci and if you're really really trying to step it

up above everybody else then you know you can grab one of your products deploy it and you can you can

perform around the clock pin testing on everything it seems i would include hipaa as well in that um

as far as yeah absolutely mike thank you for that good point yeah hipaa's gonna be uh requiring that

i think doesn't sock um require that as well stop acquiring has a pentax requirement but it doesn't

delineate how frequently other than angling but i think that needs to be updated as well if you

truly care about what you're doing and you truly have sensitive data the the desire would be that

you would be proactive and testing it minimum quarterly one of the things that we see in

out there in the in the wild you know different industries it's interesting because we work with

you know variety different industries but i think the ones that are most proactive are really those

b2b technology companies where other other organizations are relying on their

products and their environment they seem to be a little bit more um frequent

in their testing and analysis and such right and i think part of that too it goes to a bigger

a bigger picture bigger discussion about risk in general and what the organization is willing to

uh allow or or accept um the reason being with us take a b2b technology company for example

software as a service platform let's just say um their their software is their brand

right so if that goes their brand goes the company goes it's all it's all done right the credibility

out the window versus um let's take like a um maybe a regional credit union or bank for example

where there it's it's not so much you know the entity still is a brand bigger than any one

application or any one platform that they're using um so the considerations may be maybe different

right or healthcare companies same type same type of thing so it doesn't doesn't make it right to do

it do it less frequently for sure but um you know of course all companies have limited resources but

um i would encourage everybody listening that uh to to uh do something right doing something

is always better than doing nothing and it blows my mind but there's still lots of companies out

there who have never had a penetration test or haven't had one in the last three to five years

um it's startling how many haven't really yeah it's almost like if they're not beholden to some

uh compliance requirement or some client requirement um there there are a lot of

organizations that just they're not taking it on their own initiative to do them so we still hear

that argument well i've got nothing that anybody wants to steal and that's yeah this is dangerous

crazy well well that's um good overview you know some good considerations on timing and such when

you should get these things done um generally speaking too you probably get better rates if you

do these activities uh earlier in the year rather than wait till the end of the year fourth quarter

just because like we from being in the business we see everybody jumping through hoops to get their

pen test done the last minute before the end of the year and as such the higher demand they

cost more right so it's it's better to uh kind of space them out throughout the year plan be

proactive rather than trying to jump through hoops to meet a compliance requirement that said you

know there's a handful of different approaches and i figured touch on that for a little bit i mean

what are your opinions on red team approach versus a purple team approach i mean you want to start by

describing both in the differences and then just dive in a little bit because i know

it's very common in our industry for pen testing to just kind of happen in a vacuum company will

say okay give me the targets we're going to do the work and we're going to send you a report

but i don't think that's the best best approach always do you want to touch on

the differences and and pros and cons of each yeah yeah absolutely so traditionally speaking

in a mature organization you'd have a you'd have a defensive team that that was you know maybe

running your security operation center inside or you know had some security telemetry that they're

looking at you know whether you know there's a lot of products we i don't want to name right now

um in any case that's going to be your blue team all right and traditionally those are the

the defensive security team members that are you know watching the boundary watching the

log files watching things happen firewall managing changes those sorts of things that are kind of in

in that that role of defensive cyber security um another mature perspective is to also have a red

team and those would be another team of that would simulate attackers and they would help

the blue team understand what indicators of attack look like and what indicators of

compromise look like and so in in the penetration testing in the threat hunting world that's where

the that's kind of where the the desire is to be as part of the red team essentially right and and

what what silence sector does is is a version of both right we call it a purple team approach

um it's it's been you know defined prior to us of course but but essentially it's a blend right we

don't offer it in a vacuum and we recommend that that's how the the technical assessment threat

hunt or the penetration test where you're going to refer to it or however far you're going to go with

the assessment should be referred to as and what that is essentially is a

is a team-based approach so that we can train the internal response teams now you're blue you might

have a mature cyber security organization okay you may just be a small b2b and you've got you

know two network guys and a server guy that's your blue team okay they've probably because they're

they're jack of all trades and they're running the small shop they've got a lot of logging tools

at their disposal and they've probably got some parsing going on so they're already running traps

right for basic things that they just need to know to keep the business running right

um and that's a good thing about it it's one of those things where i always feel bad for for those

really really smart one it shop you know humans that are that are just keeping everything going

um because they need reprieve right they need to they need a team of three or four or five

to really do the job well but they've got a lot of capability because they're so used to

handling things that they you know they'll ride a lot of traps for all kinds of things and not

really understand that this is actually part of a blue team exercise right and so when the website

goes down and you you had some random script on a server that was just randomly pinging a you

know an item on the page that's going to tell you that something strange has happened and so

it could be an indicator of attack it could be an indicator of compromise it could just be

you know that the hosting provider went down but that's sort of the what we're looking at

when we when we when we conduct these exercises so purple team is certainly the the approach that i

would consider that you should prefer for those that are asking any any teams that conduct any

exercises or technical assessments against your assets they should work with you and they should

they should let you know when they're starting they should also let you know when they find

things right you shouldn't have to wait 40 hours or 60 hours beyond the end of the test

period to obtain results that say hey you have this critical vulnerability that i was able to get

a you know a shell out of um or you know create accounts or all these you know random things

they should let you know immediately and then you should also um turbo team exercises

are also really good because you can schedule these events and so the the teams inside right

your networking guy your it guy or if you're in a mature organization your blue team can now

know when the testing period starts and they can start looking for those indicators of compromise

or indicators of attack and then they can they can then you know go through their incident

response protocol in order to you know pretend the war game is real and what they would do to

silence the attack right and so you get you get a kind of a both benefit you're not only you're

meeting requirements from a compliance you're you're actually getting a princess to look at that

attack surface that's in the target scope but now you're also working to train the internal i.t

staff and other staff to to know what this type of traffic this aggressive scanning and these these

types of inquiries to the electronic assets look like at a telemetry level at the log files and

what types of dashboards they may have the day or or or logger irrigation they have a day

and you can train them to see what that looks like so when the testing period is over

and something happens in the wild they're better suited to acknowledge that what what this is

what's happening and then and then if necessary uh activate instant response score to call or even

shut those those activities down so i i certainly think you know purple team is the way to go

um mike what do you what do you see um is that typical what how how you feel

about yeah for stockton i think it's evolving right a long time ago it was just penetration

test was just a commodity you paid someone to come do it and then they looked at the results in the

pre-charts and said thank you very much we'll see you in a year but no i think the engagement of the

internal team is is really very beneficial um for for two reasons one they understand what you're

doing and why and where the attack vectors are it's an educational process and two it's really

testing their ability to respond and we see that to varying degrees of success and and failure um

a lot of people put so much faith in their tools that they fail to understand the human element of

it and that's where the purple team will expose those weaknesses just like testing your dr plan

or your ir plan right you need to test your daily attack plan your attack vector plan you know that

that sort of thing you need to be attacked you need to be able to test everything all the time

because things just don't automatically work right they never they never automatically work

and and a lot of times um we've seen in the small b2b world that they have they have better success

writing something custom and small than buying some big tool it's usually the the custom small

thing that um i mean a great example of slow post okay there there's really not a lot of of

tools that will i did they can prevent the attack but they won't identify it in a stream of traffic

um and one of you know somebody we know wrote a small script to just look to see if the web

you know just should check the website up or down and that was if they weren't able to tell

that slow post was the denial of service that was occurring but they knew that the site was

down right and i mean it was just they didn't need anything fancy it was a you know it was a

15 minute script you know that they just ran right so you know it's better to be clever sometimes

with what you have then you know to certainly try to spend on on big tools yeah exactly and you know

relying you know just to bring back solar winds actually as a case in point that was

just a standard update that wound up blowing up infrastructure all over the place things don't

work the way they're supposed to all the time so yeah trusted software not so trusted right

but yeah a script that you write yourself it takes you 15 minutes to write you can test

it generally works hard to explain you know what you put into it i call that organic sort of yeah

i think there's a lot of hype in in the cyber security industry uh around all the stuff that you

should have all this stuff that you know or great features and functionality but the reality is

that um companies especially when you look at mid-market and emerging size companies i mean

they need their results they they need it's not so much about being efficient as it is about being

effective right they need to be doing the right things um they don't necessarily need all the

bells and whistles i think there's a lot to be said there but you know so those are those are

some really good considerations around frequency of testing what type of approach and then finally

you know another another thing that comes up people ask well what should i get out

of a penetration test you know i went through this paid my money what do i get

for it and of course that comes down to really reporting and and hopefully some ongoing

consultation right and and hopefully those things are customized to organization and not just a

a canned approach but um what do you see as far as the most effective you know pieces of a report the

most meaningful documentation um what do you see that being for the client the sad thing is that

a lot of these reports that we put a lot of time into and a lot of people put a lot of time into

everybody reads the first three pages and that's it they look at the pretty pretty color graphs and

a lot of it gets wasted i really encourage people to actually dig into the meat of these reports

yeah good point yeah no no no good point mike and and here's the thing is that most of the

most leadership that's they don't all they care about is like did they find anything that

you know is gonna is gonna lose our business today right i mean that's kind of the common

thing that leadership wants to know right do we have something that's exploitable today

the technical teams typically are you know when something's not found but you know even us right

we always encourage them like in the reports but you know here i'll go i'll go ahead and

pull out the lectern for a minute because i have a lot of complaints in this department so i

i didn't bring the complaint box because i couldn't pull it with a one ton truck

so you know i have a lot of animosity towards some security organizations that just give you

a report that just pulls out some crap like like you know your x your x options you know aren't set

you know for cross-site scripting right your cross origins you you know or or your your secure cookie

settings aren't there or http 80 is allowed on the site even those are redirect it's like why

don't you why don't you take a moment to go out back and slap yourself and then come back and try

to give the organization something of value and i think that's really the biggest thing here is that

that report should include something valuable to you okay now there's always going to be trivial

misconfigurations that are found okay and we've talked about this in previous episodes where

there's a big difference between something that's vulnerable and something that's exploitable which

is why you know they're in the news that mike gives we're always going to hear about you know

patches that need to come out that the vendors have found themselves that say oh this could cause

you know remote code execution okay there's not an exploit out today for that that doesn't mean

that something couldn't be developed but there's a lot of time and man hours and research and

there's a lot that goes into the development of exploit okay it's not something that you can just

proof in there it is um you know depending on the type of the type of software involved

sometimes you can do that right sometimes there's a 20-minute script you can write that'll work

a lot of times it's a you know 100 or 200 hour endeavor and you've got to have access to some

source code so you want meaningful things things that are exploitable right things that i can i

have a shell script today for that i could drop and i have a payload to drop into meta

plate today and point it at your system and i get a shell that i can log in with right now right

now that's what matters right that's what should matter and that's what all these threat huds in

the pen test should be looking for and the report in the first three pages should not only say that

um but if none of that's there it should give you you know excellent marks for having a defensive

depth cyber security program right and and and protocols that you put in place um and then should

also include the reports that are going to have all those details all that you know the trivial

misconceptions that may be there i'm not saying we're not even us we're gonna let you know that

yes these trivial misconfigurations for found your web server is still open on port 80 and it

does a redirect the 443 there's no criticality exploits attack vectors that are going to cause

you any harm here however it would probably be of best practice to go ahead and consider how modern

browsers works to go ahead and close that port 80 and not even offer the redirect anymore just force

everything on 443. that's not our decision that's an architectural model change that's something

they should do but i'm not going to call this out as a high vulnerability um or a critical thing

saying that you know oh your website can get hacked now because you allow it on port 80. so

okay i'll stop mike what i miss obviously at that point i would say you know if you've got it close

anything that you don't need open first of all let's start with that you know if you don't need

port 80 close 480 and there's no reason travis should be over 480 anyway um but no i mean yeah

i mean we've seen unfortunately the position that we've seen we we have some professional paranoia

and we've seen a lot of bad things because that's why we're here we're focused on the bad things and

fix them making good things right so um yeah i i i think you spot on laurel i think that's

some very good very good points there's one other thing i want to bring up real quick and we don't

have time to talk to about it in depth today but internal pen testing really needs to be something

that needs to be considered because what we're seeing is a lot of these bulletproof you know palo

altos and f5s and although the f5 has issues right now um but anyway these bulletproof perimeters

and then the inside is a soft candy you know like an m so um we need to start talking about internal

fan testing and people need to start investing in that as well now good point man we we don't see

enough of that and when we do get an opportunity i mean that's where all the fun happens from a pen

test perspective um on the internal pen testing everybody is all put all their focus on the hard

crusted exterior it's just like the death star right no one considered the little port no one

considered that right and i'm sure there was some auditor that was like you know i don't think this

is i think this could be smaller because you know it's a womp rat could get in here and you know

technically a a missile might be able to come in here so certainly look at the internal pin testing

and and one final thing is is on that report right what you should get the report but

you don't want to share that report with third parties because even though it may not have found

the exportable items it's still going to have intimate details about your organization about

your technical controls about your technical assets you don't want to just give it away

right um so you should always whatever organization that you work with should provide you

a letter of attestation for that pen test that's a publicly digestible document that says we're a

third-party firm this is what we profess this is what we do and these are our certifications and

this is what we conducted against the environment and we have tested it you know it was a low risk

or whatever right we found so that's what you should be providing to you should get that as

part of your pin test report so that you can provide that to third parties um customers

clients may be asking for it excellent point don't don't share your penetration test reports

and so it's so amazing how many people say oh yeah that this uh prospect wanted it so he sent it to

him yeah and let me let me let me jump in too and just just to point this out like when when

it doesn't matter if it's a governance security person or yeah some prospect

they're going to put it on a sharepoint site on a public drive someplace in their organization where

who knows who has access to it keep that in mind yeah might as well just work it over to the cyber

criminals yeah well well good stuff and i think there's a lot more to talk about here i mean we

this is uh this is a deep deep topic but hopefully we're answering some of your uh questions for

those of you listening um and getting through some of the common uh things that we hear uh out there

and uh hopefully it helps you so thank you so much for joining us uh please please rate the

podcast subscribe and um that uh will help us too if you provide some some insight about what you

want to hear what questions you have we're happy to answer them thanks a lot and have a great day

take care take care pick up your copy of the cyber rants book on amazon today and if you're looking

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join us next time for another edition of the cyber rants podcast

Episode #22 - Penetration Testing: What You Need to Know (Part 3)

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