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Everything You Need to Know About Pentests

(and Why You Should be Running Yours Right Now!)

Pentesters, or ‘ethical hackers’ as they’re affectionately called, are in high demand right now.

Pentesting involves using the hackers’ own tools against them, probing for weak spots in your security provisions so that you can make proactive repairs and reinforcements to repel the inevitable real attacks when – not if – they come.

In this article, we’ll look at why pentesting is a more effective shield than simple vulnerability scans, how often you should be pentesting (and why now is a good time), and how you can choose the best partner to carry out your pentesting (hint: Shamrock Consulting Group partner is the best in the industry when it comes to cybersecurity and pentesting).

Why Pentesting Trumps Vulnerability Scanning

While a vulnerability assessment will present you with a list of weak spots in prioritized order, they are a pretty blunt tool in reality. For example, vulnerability assessments won’t be able to find out how easy it is for a hacker to breach the defenses, or what assets they will gain access to when they do.

With the sharp point of a pentest, you will be able to:

Discover what type of information a successful hack could expose

Find out how much data would be exposed

Disprove false positives (common with vulnerability scans)

Understand the specifics of a vulnerability which could give clues about how to plug the hole

From the results of your pentests, you can use a risk-oriented prioritization process to funnel InfoSec resources to where they are most needed.

Even drawing up a simple risk/impact matrix can help you with the triage process. You would then prioritize weaknesses that are easy to exploit and expose the most sensitive data before moving on to better protected, less business-critical flaws.


How Often Should You Pentest?

Every company should be pentesting at least once a year. That said, the actual frequency with which you should pentest could be determined by your compliance framework. For example, if you are bound by the PCI DSS standard, you are required to carry out a pentest at least once annually and after any ‘significant changes’ to your systems. What counts as a significant change is set out in the guidance document.

You will need to check out the compliance guidelines for ISO 27001, NIST, FISMA, HICPAA and Sarbanes-Oxley if these apply to you.

In any case, it makes sense to carry out a pentest whenever you bring a new office online, add or upgrade your network architecture, or connect new endpoints. Some companies even carry out pentests whenever software is patched or updated. Although these are designed to close up security holes, they can also open up new, unforeseen ones.

However often you carry out pentests, you should ensure a summary of the outcome is provided to the CIO so they can keep key stakeholders and decision makers in the loop.

Your VPN Could Be Your Achilles’ Heel

If you’re not familiar with the story of Achilles, shame on you! But for those who don’t know, Achilles was a fearsome and seemingly invincible Greek hero of the Trojan War who ultimately met his demise when he was shot by an arrow in his only vulnerability – his heel.

SO where is your Achilles’ Heel from an IT standpoint? It could easily be your VPN, particularly if you’ve recently set up or reconfigured your VPNs for a COVID-inspired surge in remote access requests,

Wherever a remote workforce is connecting to their parent network via a VPN tunnel, hackers know they will likely be using IKE aggressive mode.

IKE aggressive mode is designed for managing dynamic IPs (like those used by mobile employees), but this convenience comes at a cost. Unlike main mode, IKE aggressive mode exposes the pre-shared key (PSK) during authentication. This is exactly where those pesky hackers will be aiming their arrows in attempts to bring your network to its proverbial knees.

A pentest combats this hacking method by using the hackers’ own tools (e.g. a sniffer and cracker tool) to try and steal that PSK first. If successful, you now have definitive proof that you need to shore up your first line of defense.

Of course, this is only one possible attack vector. You will need to run pentests against other identified vulnerabilities in order to get a full picture of your existing security posture.

Shamrock: The Perfect Pentest Partner

Given the wild stampede for new ‘WFH-friendly’ security tools, there are a lot of vendors jumping on the bandwagon to take advantage of increased demand. This can make it tough to choose which firms offer not only the best value for money, but also the best solution for your business’ specific use case.

We’ve formed deep partnerships with the most trustworthy cybersecurity vendors in the in the industry, and we guarantee the best price from every single one of them. Also, as a vendor-neutral consultancy, you can trust us to hook you up with the best pentesting solution providers for your business needs.

We provide solutions for:

Black, White & Gray Box Testing

Cloud Pentesting

Mobile & Web App Pentesting

Wireless Pentesting

Physical Pentesting

Client-Side Pentesting

In addition to pentesting, we can also help you out with next-generation firewalls, endpoint protection and corporate email security.

We understand that every business in unique in its own right. That’s why it’s vital that you work with an objective partner like Shamrock before making any firm commitments to determine the best solution for you.

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Ben Ferguson

Ben Ferguson

Ben Ferguson is the Vice President and Senior Network Architect for Shamrock Consulting Group, an industry leader in digital transformation solutions. Since his departure from Biochemical research in 2004, Ben has built core competencies around cloud direct connects and cloud cost reduction, enterprise wide area network architecture, high density data center deployments, cybersecurity and Voice over IP telephony. Ben has designed hundreds of complex networks for some of the largest companies in the world and he’s helped Shamrock become a top partner of the 3 largest public cloud platforms for AWS, Azure and GCP consulting. When he takes the occasional break from designing networks, he enjoys surfing, golf, working out, trying new restaurants and spending time with his wife, Linsey, his son, Weston and his dog, Hamilton.

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