Cybersecurity in Plain English: How Does Ransomware Work?

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I get a lot of great questions from people in all different areas of business, but one comes up more than most: “How does ransomware even work?” Granted, we know what the goal of ransomware is – to get paid to unlock files that are locked down by a threat actor – but how does it operate, function, do what it does? Let’s dive into this topic.

Ransomware is a generic term to refer to any cyber attack where data is encrypted in order to make it unusable to a person or organization until a payment to the threat actor is made. Because locking up the data by encrypting it renders most businesses partially or totally unable to conduct business, it is a devastatingly effective form of attack, and a preferred method of threat activity these days. How it does what it does, however, is a bit more complicated; as the methods and scope of ransomware have changed over the 20-plus years we’ve been dealing with it as a security community.

Modern ransomware can be broken down into two broad categories: Single-extortion ransomware that just locks the data down, and double-extortion ransomware that also steals a copy of all the impacted data before locking it down. Each has evolved to reduce the ability of an organization to recover from backup or otherwise fix things without having to pay the threat actor, but each category is equally popular among criminal groups. 

Single-extortion ransomware works by first gaining access to a desktop, laptop, or server. This can be through one of many initial access methods, but the more commonly used techniques these days are subterfuge and exploiting a vulnerability. See the previous post at for more info on initial access. Subterfuge includes things like tricking a user into visiting a booby-trapped website, hiding malware in what appears to be a valid software application, or otherwise getting a user (or automated system) to install the threat actor’s software on a machine/virtual machine, etc. Exploitation of a vulnerability requires less (or no) interaction by a user, but rather tricks/forces an application or platform into doing something malicious by taking advantage of a weakness in the software or hardware itself. Note that threat actors are aware that anti-malware exists, and so will attempt to hide what they are doing for as long as possible and avoid triggering the anti-malware whenever possible (see dwell time below). This is referred to as “evasion,” and there are many different techniques that are used to different levels of effectiveness, depending on what anti-malware defenses are in place.  

Once they have the first device compromised, the threat actor then will typically attempt to spread their influence to as many other machines as possible (referred to as “propagation”). Since most organizational systems now use some form of Endpoint Detection and Response (an advanced type of anti-malware system), this has to be done carefully and cautiously to evade tripping detection and defensive systems. In fact, a threat actor can take weeks or even months just moving around a victim network in search of more devices and systems to take control of before they do anything like encrypting data. This is most commonly referred to as “dwell time,” with the average being about 10 days in 2023 but many sticking around for far longer to gain control of more systems. It isn’t uncommon to see dwell times stretching into months as double-extortion attacks become more common.

More commonly these days, threat actors will also attempt to disable backup solutions and try to weaken or disable anti-malware solutions as they go. This allows them to spread further, and to ensure that once they do spring the trap, the organization won’t have recent backups to restore from. Both actions make it more likely that the victim organization will pay to have their data unencrypted. Remember that ransomware is a business – a criminal business, but still a business – so the more likely a victim is to make a payment, the more money the criminal business generates. Additionally, many modern threat-actors will install back-door systems which will allow them to re-enter the organization’s systems if the organization does choose not to pay – so that the threat actor can re-encrypt over and over until they get money. 

Once the threat actor has gotten onto as many systems as possible and made sure things like backups have been rendered useless, then single-extortion ransomware enters its final stage. Some, most, or all of the data on each infected machine is encrypted using a key only known to the threat actor. Without going into too much detail here, threat actors use a theory known as asymmetrical encryption – meaning that the key that encrypts the data cannot be used to decrypt it. So even if the organization captures the encryption key, it won’t be useful in getting back to business. Once done, the threat actor either displays a message on the infected systems and/or directly contacts the organization to demand a ransom in exchange for the decryption key; and the attack is then finished.

For double-extortion ransomware, the game changes a bit. While all of the above steps still happen, there is another step added in between the propagation phase – where the threat actor tries to compromise as many systems as possible without being caught – and the encryption phase. As they move across the organization’s systems, the double-extortion ransomware threat actor begins stealing a copy of the data that they discover. There are many methods for performing this step, but the most common involve sending a copy of each file to cloud storage that the threat actor has access to. Many have asked why cloud providers don’t prohibit this activity and stop double-extortion ransomware, and the answer to that question will be in an upcoming article, but suffice it to say that currently; they really can’t police this type of data transfer in order to stop it. Data exfiltration can occur quickly, or very quietly – with different threat actors preferring different techniques in a trade-off between getting everything fast or evading defenses but taking longer to get the job done. 

This dataset is held until after the threat actor encrypts the original data on the organization’s systems, and the data theft can go on for as long as the threat actor is able to dwell within the organization. This means that not only can all current data be stolen, but any new data can also be siphoned off and stolen as the attack progresses. With dwell times adding up to potentially months, this can mean a great deal of current data can be stolen as it is created and modified by employees. 

Once the trap is sprung and the original data is encrypted, the threat actor now has two threats they can use to extort a payout from the victim organization. First, they will offer the decryption key in much the same way as with single-extortion ransomware. Secondly, they offer to destroy their copy of the data if the ransom is paid; but threaten to release that data to the general public if the ransom is not payed. So, even if an organization can recover without paying the ransom, they still must contend with the fact that highly privileged data could be released to the outside world unless they pay. For organizations like law firms, healthcare companies, payment processors, and other organizations that hold extremely privileged information, such public release of the info could be devastating and even trigger massive regulatory fines and penalties. Even a business that writes off the encrypted data as a loss may not be able to weather all of that data becoming public knowledge to anyone who wishes to view it. The hit to customer trust, regulatory fines, impact to stock prices, loss of investors, and other factors make such a release of data something many companies cannot withstand without going out of business. 

Some ransomware threat actors have even taken things a step further with so-called triple-extortion attacks. The data itself is encrypted, the stolen data is threatened to be released to the general public, and the threat actor also threatens persons and companies that appear in the data to try to get them to pay in addition to the company the data came from. For example, if a ransomware actor compromises a hospital, the data on the hospital data-systems is encrypted, a the threat actor threatens to release the copy of that data which they hold to the general public, and the threat actor reaches out to individual patients and demands that they also pay money to keep their own data that was in the stolen data-set from becoming public. This maximizes the payout the threat actor can get, and makes it even more likely that the original victim organization (the hospital in this scenario) will pay them to make the whole problem go away. 

Many have asked me if they should pay the ransom. While I can’t speak to every situation that ransomware can create, my overall recommendation is not to pay if there is any other way to get back to business. Paying the ransom has several negative effects: First, you’re giving money to one or more people who admit they are criminals. There’s no guarantee that they’ll do what they say they’ll do if you pay them, and they may have back-door access to continue harming your organization even if they do give you the decryption keys. There’s also no way to validate that they deleted their stolen copy of the data, and in fact law enforcement was able to find supposedly deleted data on threat actor systems they took control of in raids and shutdowns []. Second, every time the threat actor is paid, it encourages more threat actors to get into the ransomware business to make money. Third, depending on who the threat actor is and where you are, it might be against the law to send money to the threat actor at all and therefore expose your organization to even more regulatory and/or legal issues. Some information on this for US companies can be found here: . While there are some cases where paying the threat actor is the only way to resolve the situation, every organization should think long and hard about the repercussions to their own business and to the greater business world if they do so. 

Ransomware is an insidious threat that is growing every day. With double- and triple-extortion techniques growing in popularity, even the ability to recover without paying the ransom doesn’t remove the threat that the criminals can hold over an organization and its customers. That being said, it is not all doom and gloom. By keeping software updated, not interacting with links in emails or attachments that come in with them, and practicing basic online hygiene; users can thwart a large number of ransomware attacks. Exploitation of weaknesses in software will still be a problem, and organization must address these by utilizing additional security controls to compensate for the weakness, but effective strategies do exist for minimizing the potential to be struck by ransomware. Together, we can make it less lucrative for a threat actor to use ransomware, causing their business models to break and making the net a safer place. 

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