Last updated at Fri, 15 Sep 2023 14:36:47 GMT

This post is co-authored by Chris Henderson, Senior Director of Information Security at Datto, Inc.

Ransomware has focused on big-game hunting of large enterprises in the past years, and those events often make the headlines. The risk can be even more serious for small and medium-sized businesses (SMBs), who struggle to both understand the changing nature of the threats and lack the resources to become cyber resilient. Ransomware poses a greater threat to SMBs’ core ability to continue to operate, as recovery can be impossible or expensive beyond their means.

SMBs commonly seek assistance from managed services providers (MSPs) for their foundational IT needs to run their business — MSPs have been the virtual CIOs for SMBs for years. Increasingly, SMBs are also turning to their MSP partners to help them fight the threat of ransomware, implicitly asking them to also take on the role of a virtual CISO, too. These MSPs have working knowledge of ransomware and are uniquely situated to assist SMBs that are ready to go on a cyber resilience journey.

With this expert assistance available, one would think that we would be making more progress on ransomware. However, MSPs are still meeting resistance when working to implement a cyber resilience plan for many SMBs.

In our experience working with MSPs and hearing the challenges they face with SMBs, we have come to the conclusion that much of this resistance they meet is based on under-awareness, biases, or fallacies.

In this two-part blog series, we will present four common mistakes SMBs make when thinking about ransomware risk, allowing you to examine your own beliefs and draw new conclusions. We contend that until SMBs resistance to resilience improvement do the work to unwind critical flaws in thinking, ransomware will continue to be a growing and existential problem they face.

1. Relying on flawed thinking

I’m concerned about the potential impacts of ransomware, but I do not have anything valuable that an attacker would want, so ransomware is not likely to happen to me.

Formal fallacies

These arguments are the most common form of resistance toward implementing adequate cyber resilience for SMBs, and they create a rationalization for inaction as well as a false sense of safety. However, they are formal fallacies, relying on common beliefs that are partially informed by cognitive biases.

Formal fallacies can best be classified simply as deductively invalid arguments that typically commit an easily recognizable logical error when properly examined. Either the premises are untrue, or the argument is invalid due to a logical flaw.

Looking at this argument, the conclusion “ransomware will not happen to me” is the logical conclusion of the prior statement, “I have nothing of value to an attacker.” The flaw in this argument is that the attacker does not need the data they steal or hold ransom to be intrinsically valuable to them — they only need it to be valuable to the attack target.

Data that is intrinsically valuable is nice to have for an attacker, as they can monetize it outside of the attack by exfiltrating it and selling it (potentially multiple times), but the primary objective is to hold it ransom, because you need it to run your business. Facing this fact, we can see that the conclusion “ransomware will not happen to me” is logically invalid based on the premise “I have nothing of value to an attacker.”

Confirmation bias

The belief “ransomware will not happen to me” can also be a standalone argument. The challenge here is that the premise of the argument is unknown. This means we need data to support probability. With insufficient reporting data to capture accurate rates of ransomware on SMBs, this is problematic and can lead to confirmation bias. If I can't find data on others like me as an SMB, then I may conclude that this confirms I'm not at risk.

Anchoring bias

I may be able to find data in aggregate that states that my SMB’s industries are not as commonly targeted. This piece of data can lead to an anchoring bias, which is the tendency to rely heavily on the first piece of information we are given. While ransomware might not be as common in your industry, that does not mean it does not exist. We need to research further rather than latching onto this data to anchor our belief.

Acknowledge and act

The best way to combat these formal fallacies and biases is for the SMB and their MSP to acknowledge these beliefs and act to challenge them through proper education. Below are some of the most effective exercises we have seen SMBs and MSPs use to better educate themselves on real versus perceived ransomware risk likelihood:

  1. Threat profiling is an exercise that collects information, from vendor partners and open-source intelligence sources, to inform which threat actors are likely to target the business, using which tactics.
  2. Data flow diagrams can help you to map out your unique operating environment and see how all your systems connect together to better inform how data moves and resides within your IT environment.
  3. A risk assessment uses the threat profile information and overlays on the data flow diagram to determine where the business is most susceptible to attacker tactics.
  4. Corrective action planning is the last exercise, where you prioritize the largest gaps in protection using a threat- and risk-informed approach.

2. Being resigned to victimhood

“Large companies and enterprises get hit with ransomware all the time. As an SMB, I don't stand a chance. I don't have the resources they do. This is hopeless; there’s nothing I can do about it.”

Victim mentality

This past year has seen a number of companies that were supposedly “too large and well-funded to be hacked” reporting ransomware breaches. It feels like there is a constant stream of information re-enforcing the mentality that, even with a multi-million dollar security program, an SMB will not be able to effectively defend against the adverse outcomes from ransomware. This barrage of information can make them feel a loss of control and that the world is against them.

Learned helplessness

These frequent negative outcomes for “prepared” organizations are building a sense of learned helplessness, or powerlessness, within the SMB space. If a well-funded and organized company can't stop ransomware, why should we even try?

This mentality takes a binary view on a ransomware attack, viewing it as an all-or-nothing event. In reality, there are degrees of success of a ransomware attack. The goal of becoming immune to ransomware can spark feelings of learned helplessness, but if you reframe it as minimizing the damage a successful attack will have, this allows you to regain a sense of control in what otherwise may feel like an impossible effort.

Pessimism bias

This echo chamber of successful attacks (and thus presumed unsuccessful mitigations) is driving a pessimism bias. As empathetic beings, we feel the pain of these attacked organizations as though it were our own. We then tie this negative emotion to our expectation of an event (i.e. a ransomware attack), creating the expectation of a negative outcome for our own organization.

Acknowledge and act

Biases and beliefs shape our reality. If an SMB believes they are going to fall victim to ransomware and fails to protect against it, they actually make that exact adverse outcome more likely.

Despite the fear and uncertainty, the most important variable missing from this mental math is environment complexity. The more complex the environment, the more difficult it is to protect. SMBs have an advantage over their large-business counterparts, as the SMB IT environment is usually easier to control with the right in-house tech staff and/or MSP partners. That means SMBs are better situated than large companies to deter and recover from attacks — with the right strategic investments.

Check back with us next week, when we’ll tackle the third and fourth major fallacies that hold SMBs back from securing themselves against ransomware.

Additional reading:


Get the latest stories, expertise, and news about security today.