Adapting the classical art of penetration testing to the cubist world of cloud – Digitalmunition

News Adapting the classical art of penetration testing to the cubist world of cloud

Published on August 13th, 2019 📆 | 8575 Views ⚑


Adapting the classical art of penetration testing to the cubist world of cloud

Many technical practitioners may believe that, at the end of
the day, penetration testing is penetration testing. Proper penetration
testing, however, is an art that must adapt over time. As an artist’s tools,
materials, and media evolve, art evolves. With this evolution in “technology,
techniques and approaches must change as well.

Our “IT medium” has changed. With IT models fundamentally
shifting from “on-prem with a little cloud thrown in” to a cloud-dominant
implementation, penetration testing approaches must fundamentally evolve, just
as approaches to fine art have evolved through the influences of culture,
tastes, and emerging tools of the trade.

A mere 50 years ago, our industry began to shift from a single-user
to multi-user computing model. Multi-user systems were considered a risk, and
penetration testing saw its roots in military operations, testing the security
of the new multi-user, time-shared computing systems. Thus began the
cave-painting era of penetration testing: relatively brutal techniques against
simple systems (compared to todays).

30 years ago, ARPANET gave way to the Internet, and by the
mid-nineties, we had interconnected and exposed systems across the globe. These
changes exposed vulnerable systems (remember Nimda and Code Red?), which altered
the course of security testing and brought in a new color pigment in the
proverbial security palate, called “patch management.” Penetration testing
evolved to focus on evaluating exposed services on the operating system of
servers in an attempt to find unpatched systems.

The internet brought with it web applications, which broadened
the focus again. As the advent of oil painting provided a new dimension of
depth and breadth of color and expression, so did the addition of application
attacks to the network attacks in the penetration tester’s arsenal. SQL
injection, then cross-site scripting and other high-profile attack techniques
emerged, bringing application security to the forefront of security concerns.

In 2006, Amazon launched Amazon Web Services (AWS), and
Google launched Google Docs, commercializing the concept of cloud computing. This
major milestone didn’t significantly change the way penetration testing was
conducted since the days of the managed service provider; it simply broadened
it. While a traditional managed service provider was rather unlikely to permit
penetration testing, the major cloud providers embraced it to gain a deeper
understanding of their own shortcomings. The most important aspect of these technology
launches was that they were the leading edge of the next phase of evolution:
serverless architectures.

Some say that serverless architecture represents the biggest
change to the IT ecosystem we’ve seen in decades. This change would move us
past virtual machines and containers and into a code-only world, taking the “ops”
back out of “DevOps” (and baking “sec” back into “dev”). This has the capability
to break a lot of existing practices and processes, from challenges with
monitoring and debugging, securing the much larger attack surface, and the
inevitable vendor mating that comes with developing on a specific cloud

How will our current incarnation of the art of penetration
testing evolve to meet this oddly shaped, abstract world? To start with, it’s
no longer nearly as simple as traditional “network” attacks versus
“application” attacks – we must adapt and address the entire attack surface of
the solution. To that extent, it’s quite difficult to identify the entire
attack surface of the solution without collaborating with the DevOps team
responsible for it. How is one to tell what serverless infrastructure components
are in play? Even in the simplest solution I can imagine – a simple website – it’s
exceedingly difficult. I’ll use a quick example and reference AWS components
(simply because that’s what I know best). Let’s say we’re building a simple

  • Static content could be hosted in S3 OR on server-based infrastructure.
    Static content could be distributed by Amazon CloudFront OR through server-based infrastructure.
  • Dynamic content comes via an AWS API gateway, OR possibly through a web service
    hosted on EC2.
  • AWS API gateway calls could call Lambda functions. Lambda functions likely are in a VPC, but not necessarily.
  • Those Lambda functions might query and return data from RDS, ElastiCache, S3, DynamoDB,
    RedShift, or EC2? The possibilities are almost endless!
  • Authentication? You’ve got to guess it’s IAM,
    but it might not be.

Given the vast array of services available around which to
build even this simple app, it eliminates black box application testing from
even being considered an option.* The only option to comprehensively address
the components is to understand the architecture and the attack surface of each
component before embarking on a penetration test. We will require a
collaborative approach between the tester and DevOps team, developing a threat
model for the application before engaging in any kind of testing. Working from
that threat model, attack scenarios could be established and prioritized for

A cloud architecture-focused threat model assembled for
penetration testing purposes should describe the architecture, identify the
entry points within each architecture component, and identify dataflows between
components. The threat model must be used to inform the penetration test and,
for best results, inform the remediation recommendations as well. Without it,
the test may fail to address risks across the solution.

Is serverless computing a revolution in the cloud? Will it
be a revolution in application penetration testing? It could be akin to how the
development of the camera drove the beginning of modern art. Artists questioned
the purpose of painting, and the Picasso’s and Pollock’s ultimately drove the cubism
and abstract expressionism movements in response. Just as painting evolved from
watercolors on limestone and plaster to the “pop art” we see today, our
penetration testing process must move from an “offensive security testing”
approach to a collaborative “threat modeling” project.

* Not that black box testing ever was a viable option for
testing; it is too generic an approach. Bob Ross had happy little trees, but they
pale next to a Van Gogh.

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