A Tale of Two Phish: How Phishing Leads to Ransomware

Oct 13, 2021 | Security, Solutions

It was the best of times, it was the worst of times, it was the age of phishing, it was the age of ransomware, and the story goes on. The security industry continues to see how ransomware devastates organizations. According to a Fortinet 2021 report, the average weekly growth of ransomware is seeing an increase of around 10 times more than one year ago. (1) Extortion has become the norm in cybercrime and there is a massive financial benefit. Insurance companies continue to write policies that simply pay out millions of dollars in ransom demands despite the warnings of tired, frustrated technology professionals. Criminals are ramping up operations, emboldened by the guaranteed payoff. On top of this, security vendors stand waiting and alert, like a green recruit ready for their day on the front line. We have successfully created a world where the criminal knows big money is right around the corner. However, we can’t fool ourselves into thinking big businesses with large IT budgets and huge security groups were the only targets. We would also be severely inaccurate if we thought it all happens like some bad movie plot – “I’m in the firewall!” These scenarios are not realistic. Other forces are in play. They are organic in nature. We must not forget the human element to all of this: our end users.

One goal we may all have is to not have a resume generating event. Sure, common frameworks such as NIST and MITRE ATT&CK can most certainly create a base for proper protections, but the human element is often overlooked. This is a tale of two phish. We would miss the mark if we did not talk about the phishing, the whales, and the spears. Some may ask, “What is phishing?” Phishing is simply defined as an attempt to somehow get Alice or Bob to divulge sensitive information. Alice gets 100 emails a day; she is experiencing infobesity.  It’s easy to see how a phishing attempt could be seen as a legitimate email. In an office down the hallway, Bob, the CEO, needs her to see an invoice and get it processed ASAP. Spearphishing goes after Alice, the little fish.  Bob, on the other hand, is a very big whale. With whalephishing, the CEO is considered the main course. Alice receives the email and after a click, a reverse shell is in place; none is the wiser. Big surprise, that was not Bob. That was Nicole and she is four states away. The pesky macro that Nicole injected inside the email sets off a chain of events that would later cost money, time, and reputation. There were methods to gain that traction and persistence. Nicole targeted this MSP because she knew the initial attack surface was small but grows exponentially as enumeration exposes the MSP’s client base.

Again, let’s be honest; with power and position comes risk. Executives and the C-Suite are busy. Phishing scams are just not a priority to upper management. A 2020 Forbes article tackles this quite eloquently, “The longer management ignores the threat posed to customers by phishing attacks, the more likely an enterprise will repeatedly experience this type of attack.” (2) It’s a simple mistake to click on that urgent email from the CEO. Malicious actors know this; they bet on success. Phishing can be done via an email, a phone, or an SMS message. The objective is to become Alice’s friend, find her trust, and eventually gain access. Alice and Bob are not the only targets. Vendors and supply chains are bigger fish and are priority number one.

Supply chain attacks have been in the news recently. Remote management organizations have shown us how brittle our security posture is. These 3rd party vendor applications sit on a customer’s network without restriction and with elevated privileges. Remote management organizations have persistence into a network via a remote monitoring and management (RMM) application; it is there by design and provides access to client devices and networks. Who are these clients?  Large companies use RMM solutions, but a large swath of attacks target Managed Service Providers and Cloud Service Providers (CSP) via an RMM solution. Supply chain attacks are one of the most serious vectors for compromise. By phishing and intruding inside the network of [insert remote management company], a malicious actor can obtain access to update repositories, vendor VPN connections, and other organizational controls. This is where MSP’s and CSP’s are advised to exercise caution.  Supply chains and vendors are the crown jewel for criminals. Securing infrastructure by deploying network access controls, enabling endpoint protection solutions, and standing up firewalls is not sufficient. Employee education, phishing simulations, and security minded incentives will help to drastically reduce the number of security incidents in any organization. MSP’s and CSP’s must be prepared to handle a security event for their customers but also deploy good digital hygiene in their own environments.

We see Alice and Bob every day. We know them, we work with them. In short, we are Alice and Bob. Our goal is to avoid Nicole at all costs. To avoid phishing attempts, we must first recognize the threat so we can eliminate it. Verify everyone and when in doubt, contact the person that sends an attachment. Hover over links and verify the domain but avoid clicking on links in emails, if possible. Get into the habit of reading the voice on the other end of the call. Are they being extremely nice and asking how your family is, how the baseball game is? Is this person trying to slide into your life for any curious reason? Be wary and have common sense but if anything, perform the following:

Trust no one, verify the rest.


David Moore
Solutions Engineer, Cloud and Security


(1) Fortinet, Inc. 2021. Global Threat Landscape Report
(2) Stolfo, 2020, Why The C-Suite Should Care About Phishing Attacks Against Customers, accessed 20 September 2021, <https://www.forbes.com/sites/forbestechcouncil/2020/04/01/why-the-c-suite-should-care-about-phishing-attacks-against-customers>




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