General Cyber and IT Security

Do I Pay the Ransom? Insights from an Incident Responder

When people meet me, and I identify as a Cyber Incident Responder who has been a part of several ransomware extortion cases, everyone asks, “Should I pay the ransom if I am attacked?” I am about to share some insights gathered while working with companies that faced these questions in real life. Now, there are some people out there who hold absolute hardlines on this position, and while hardlines are always a good place to start, the reality is that many companies need to step off that first position and find a position that works best for them. 

Each company needs to make its own decision in concert with qualified specialized legal counsel. In sharing this information, I hope it helps you determine whether you should pay their ransom if that fateful day arrives. Viewer discretion is advised.

First, You may not even need to pay at all.

Our good friends at CISA and the FBI have developed several tools to decrypt files damaged by many popular threat actors. They are 100% free to acquire and use. CISA has created the ESXiArgs-Recover tool to assist networks whose ESXi infrastructure may have been encrypted.1 The FBI has created keys for victims of Blackcat, AlphV, and Sphynx ransomware variants.2 Obtaining the keys from these groups will strengthen your ability not to have to pay ransom much.

Now, the Company hard line.

At a recent security conference that I was speaking at I was fortunate enough to be sitting at a table with a bunch of local liaisons to a government agency that is very involved in ransomware activities. When one of the gentlemen asked me what I was speaking on, I told them to title my session, which was called “ESXi Host Protection 2024, why you can’t ignore this anymore”. This session was on ESXi hosts targeted by ransomware threat actors and how to prepare/prevent such attacks. 

Upon hearing my session title, the gentleman asked me my thoughts on paying the ransom while simultaneously telling me his staunch view. Unsurprisingly, he echoed the agency line that nobody should ever pay the ransom. Paying ransomware is the equivalent of negotiating with terrorists. You should never negotiate with terrorists. It just encourages them to continue. That is a valid point.

I stated that, in my experience, every situation was unique. Then I mentioned that I had recently worked with a company willing to pay their ransom even if they did not receive the encryption keys, which sometimes happens. (Newsflash, criminals are not honest. More on that later). Puzzled, the gentleman across the table asked why they would do that. My response was, well, it was simple. 

They viewed themselves as having a large liability for possibly causing the ransomware incident to take place in the first place. Therefore, their legal counsel was telling them that since they may not have done everything, they should have to protect the data; they now need to do everything possible, including paying a ransom, to demonstrate (to potential future judges and jurors) that they did everything they could to recover the data.  The company was preparing itself for pending litigation due to the cyber incident. 

I could tell by the look on his face that he didn’t like the answer. but he nodded and said he understood why someone would do that. Then, he immediately pivoted back to his agency’s line. As you can see here, the theory of never paying the ransom has real merit. But when the theory makes first contact with the enemy, companies need to be ready to adjust their stance. In this case, what was best for the government agency wasn’t necessarily the best thing for the business affected. The two can co-exist and do. Not paying is a good position to start at, but be ready to pivot if needed.

Can you restore and recover in time?

One factor to consider in whether you’ll pay the ransom is, once you receive decryption keys, how long will it take to decrypt your data (if you even receive the key)? The way ransomware works is that it’s designed to encrypt data for maximum impact rapidly. It can take just hours to encrypt a medium to large-sized network completely. Still, it is extremely slow to decrypt the same data, especially large data sets (hundreds of gigabytes or more). Therefore, you need to plan accordingly for just how long your restoration will take once you begin.

I witnessed one company days away from financial ruin and closing its doors for good due to the vast amount of encryption that had taken place with ransomware in its environment. The timing of the attack could not have been worse, and that was the point. The ransomware gang had stalked this company internally and knew the business cycle and when the company was most vulnerable. These people were under tremendous pressure to get their systems restored. Therefore, paying the ransom seemed viable, or at least harder to say no to, when all the other options may have led to total failure.

But here’s the catch. Is it really a viable solution? What if this company could not get the data restored within a couple of business days it needed? What if the ransomware actors don’t respond to your request or payment as quickly as you need them to? Threat Actors don’t work under Service Level Agreements. 

In this scenario, if it will take you a week or more to restore all the necessary data, what’s the point in paying when you exceed your window for restoration? The harm will happen either way, so you might as well not pay. Many people don’t factor in the time it takes to restore the data or systems in their decision-making process. They should. This might be a reason, albeit a sad reason, not to pay. Better yet, if you know that you can restore your systems from backups in a rapid time, the need to pay the ransom may no longer exist or never exist to begin with.

Should you trust a criminal?

Do I really need to answer this one? Despite working with some smart businessmen and women and helping them navigate some tough waters, I am always surprised when they express shock when the ransom is paid, and the other side doesn’t completely hold up their end of the deal. Maybe this is because they are looking at this like they would negotiate a contract for services with AT&T. Now, while the feeling of being held up for ransom and having to deal with poor customer service may be the same in both scenarios, I assure you that they are not the same situation, or at least not yet. Please repeat after me.




The recent takedown of LockBit Ransomware Group leadership shows what I have advised many customers about. Just because someone says they will delete your stolen data doesn’t mean they will. There are ways to easily fake the evidence that ransomware gangs provide as proof of deletion. You are taking a thief at their word that they will do what they claim after they just willfully wrecked your business. 

Investigators who took down LockBit have found massive amounts of stolen victim data on the servers of the ransomware gangs, even those victims who paid and were given proof of the deletion. The gangs hoarded the data for the next round of extortion or marketplace sale to other threat actor groups. While you are negotiating with them, the threat actors are selling your data to other criminal groups so that they may attempt extortion later.

To make things worse, the ransomware group is also selling to others how they initially gained access to your network to steal/encrypt your data, to begin with. The goal is that someone else will attack your network when they are done in hopes that the initial access was not properly fixed. Now, the ransomware group will have deniability that they were involved with your second or third cyber incident, thus giving them the appearance of credibility when there never was any. 

Not only is this being discovered by law enforcement, but now, sadly, a new wave of victims is emerging: those who paid group #1 but are now being extorted by group #2. All this being said, there has always been evidence of some ransomware groups skipping town with the ransom and not providing the decryption keys or not providing decryption keys that work properly, which is just as bad. Like before, the ransomware gang can claim that they held up to their end of the deal by giving you the working keys when they did not or falsely advertise their capabilities. There is no honor among thieves.

Insult to Injury

It should surprise no one that the cost of cyber liability insurance and services around ransomware has skyrocketed. Just like your auto insurance rates increase when you open a claim for an accident, your cyber liability insurance will most likely increase dramatically, or you may get dropped completely when the matter is over. Those are business costs that sometimes get overlooked during the heat of the battle. You may have paid $25,000 in one-time ransom, but if your insurance premiums go up $25,000 per year for every year you are in business from now on, is this a wise financial move? 

I hate to paint Insurance as a bad guy, as they provide a much-valued service for businesses today. But at the end of the day, ransom payments are a business decision with wide-reaching implications long after the battle. Costs are still costs. Paying a ransom might cost your business more in the long run than enduring the short-term financial pain today.

Final Advice

I will summarize what you need to know and incorporate it into your business equations to determine whether you should pay the ransom.

1. Check to see if your variant of ransomware is one that either CISA or FBI has decryption tools available before you start any discussions on paying ransom.

2. You cannot trust the extortion groups regarding their capabilities or commitments. They will lie, and they have. They are criminals.

3. Ransomware/Theft negotiations ARE NOT enforceable business contracts. Don’t treat them as such. You can’t sue them for breach of contract when they double-cross you.

4. Don’t get caught up in the emotions. I’ve seen people think this is a scene from a movie and get the adrenaline rush of “talking to the bad guys” or have strong emotions as they feel violated or the pressure of the situation gets to them. It’s human. But adrenaline and emotions skew the rational, analytical conversations that need to take place. Take a breath before moving on.

5. Don’t do this alone. You need to have good, experienced legal counsel advising you along the way.

6. Don’t do this alone. You need a good, experienced Incident Response Team to help your company’s recovery efforts while you have a business conversation with legal counsel. Remember, these gangs are selling information on how they broke into your systems. You need experienced experts to determine how they did it and provide a path to remediation so that future attacks can be properly fended off. While multitasking during negotiations with Khan may have worked for Captain Kirk, in the movie The Wrath of Khan, it is not a good foundation for success, and we’re not Captain Kirk.7. Companies that prepare for ransomware/breaches fare better than those that do not. Do you know how long it will take to restore your systems? Is this good enough for a business to survive? The best time to handle ransomware is during the preparation stage when you can plan your defenses and response strategies and when things are calm. Engage with an experienced Incident Response team to help you prepare. Your Cyber Insurance carrier may even have plans or programs to help you at no additional cost. Don’t overlook these policy benefits.


8. Finally, don’t hide from regulators. Some business leaders discuss the pros and cons of not disclosing the breach if they get their data back. It’s been my experience that you were breached will eventually come to light, whether you want it to or not. You won’t be able to hide this forever.

If you become a victim, there is no one-size-fits-all answer for dealing with extortion gangs. Learning what happened to others in similar situations may help you consider those facts while determining what to do. I never fault a company for doing what is best for them in these situations. What works for one company may not be appropriate for another. If you are a ransomware or data theft victim, the experienced team at SecurIT360 is ready to lend a hand. You can contact us at I hope this has been helpful and we can meet someday under favorable circumstances and not when my team’s response services are not needed.

1 To obtain a copy of ESiArgs-Recover tool, visit CISA’s GitHub page at:

2 For the FBI tool, you need to open an IC3 report at:

In the description, ask for the specific decryptor tool that you need to route your request to the right team. (Blackcat, AlphV, Sphynx variants only).

Digital Forensics | Incident Response

Transforming Your Security: Insights from Coaching a Collegiate Cyber Defense Team


By day, I am a full-time Information Security professional with nearly 20 years of industry experience. I have worked for companies as small as a few dozen employees to some of the largest organizations in my state and other mid-to-large sized companies in between. About 5 years ago, I answered the call to give back and began to work in the evenings as an Adjunct Professor in a local Cyber Security program. It has been rewarding to work to train the next generation of the cybersecurity workforce.

Early in my tenure, my campus fielded a Cyber Security Competition Team. Throughout the year, there are competitions where youngling cyber practitioners are given real-world challenges and opportunities to get some priceless experience. The other coaches of this team and I are proud that most of our students get job offers on the spot from companies of all sizes and industries based on their performance in these competitions. To date, our job placement rate is near 100%.

The following contains lessons learned that I had the opportunity to observe and experience firsthand throughout the genesis and maturation of a Collegiate Cyber Defense Team. As a highly experienced and credentialed security practitioner, I am still amazed at how many companies struggle with cybersecurity. I share the following, hoping to show many that good security doesn’t have to be hard or expensive and that even old security dogs can learn new tricks.

Lesson #1. No plan survives contact with the enemy.

Everyone has a plan until they get punched in the mouth.” 

-Mike Tyson

Any theory can be good until it hits the battlefield. When we first started, we followed the methodology that when you have a compromised box, the first thing you should do as a part of containment and eradication is identify the missing patches and quickly apply those patches to keep the Threat Actors (TA’s) out.  In theory, this works and makes sense. Patch Management is a part of good hygiene that every network should implement. However, we only have six hours to complete our mission during the competition. We don’t have endless days post-detection. In this environment and conditions, we must change our focus.

Initially, our teams were quickly getting onto their perspective boxes and attempting to download the patches, wasting hours they didn’t have. The result was a constant seesawing back and forth with the Offensive Team (Red Team)* because they could not properly contain the systems using this method. So, in this situation, rushing to patch as a mitigation step just didn’t work. So that led us to change how we were doing things going forward.

Our methodology shifted to applying patches at the very end of the process versus being one of the first things our teams do. Now, our teams focus on getting control of their boxes and removing the threat actor. Typically, they just find the sorts of Indicators of Compromise (IOCs). Once the student has maintained network control over their system, other mitigation steps and compensating controls are deployed. This further decreases the pressure for patching. From year to year, we saw a rapid increase in the performance of the team by then focusing on the core containment and eradication rather than on the remediation steps. Patching is still important. It is just not as important as we had initially thought. Compensating controls can equally mitigate the vulnerability, often much quicker than patch deployment. This leads us to our next lesson.

Lesson #2. Do the basics and do them well. 

Ransomware Threat Actors are very good at the basics, and this shows against companies that aren’t.”   

-SANS DFIR Aug 2023

Everyone has heard of the KISS (keep it simple, stupid) process method. This is especially true when defending your system against a strong, active, offensive adversary. Many students who join and compete on the Cyber Team have little to no real-world IT experience. They spend their weekends preparing for the competition by reviewing basic checklists and tasks. These exercises are done repeatedly, just like practicing free throws in basketball.

At one of our most recent events, a student on the team was new to managing a Linux BIND server. When the starting gun fired, almost immediately, the entire network services went down. This is not uncommon in these sorts of competitions. Students in all positions on all teams struggled to get going and get their services back up and running. This student, who was new to BIND, followed their training and worked off the checklists and task lists.  Shortly after that, the BIND server was back up and running and remained up for the entire competition despite a constant barrage from the Red Team. This student’s work was recognized during the competition. This student received public credit from judges and a merit award for their work.  When the student was asked by other students what they did to get working while others still failed, the answer was that they just stuck to the checklists. While others tried kitchen sinks and chased sexy tactics, this student “KISS’d” the Red Ream goodbye. Doing the basics well can be its own no/low-cost mitigation tool.  This leads us to our lesson.

Lesson #3. Network control is a force multiplier.

Don’t be afraid to challenge the pros, even in their own backyard.”

-Colin Powell

You rarely get some security theories exercised in real life. Observing these competitions has allowed me to see some theories put to the test. To give some context, the network environment is prepared before the students can log in and begin. The Red Team pillaged the network the night before, leaving their rootkits and shells behind. Often, systems are further damaged to hamper the response efforts of the students. I think this is a bit much. The Red Team already has the advantage of network reconnaissance and unfettered access to plant their tools. It is unfair for some of the country’s best Red Teamers to get to further damage systems, handicapping the rookie students who are outclassed in skills and experience. I’m not alone in this sentiment. The other coaches on our team agreed.  We decided to take it to the Red Team to prove that none of their tools would work if we controlled the network.

In our first attempt, we fully leveraged all aspects of the Layer 7 Firewall from Palo Alto that was being utilized in this round of the competition. (In each round, different technologies are used, such as PFSense or Cisco).  We had one very enthusiastic student buy into what we were trying to do.  He took Lesson #2 to heart and learned the basics of that security appliance. On competition day, within the first hour, this student completely evicted the Red Team from the network and kept them out for the duration of the competition. He showed that a properly configured and fully utilized Layer 7 firewall is tough to bypass, even by the pros who more than had a head start. Our success led to future competition rule changes, including the increased use of legacy traditional firewalls with fewer capabilities. We proved that someone with the right security tool can properly defend themselves against a literal army of invaders with Cobalt Strike. Score one for the home team.

Now that we had made a name for ourselves, future rounds were met with the wrath of the Red Team. Brittle egos are slow to mend. Whenever the Red Team wanted to handicap the field, they ensured that any firewall, other than a Layer 7 firewall, was used. This proved that our concept was sound, but now we had to adapt. The battle line had moved.

We moved the control of the network to the host level. In our basic checklist and task lists, we included steps to manage the endpoint firewall manually, whether it was IPTables or Windows Firewall. Students drilled on locating the connections to their system and evaluating whether it was truly needed. In other words, we implemented Zero-Trust networking a little before it became a marketing craze. It didn’t matter what was protecting the perimeter; the hosts were actively rejecting connections from sources that were not allowed. Eventually, the Red Team would pivot to a trusted host to launch an attack, but the time was running out by that point of the competition. Time and again, when our students achieved control of their host and managed the local firewall properly, the Red Team faced greater difficulty in achieving their goals, even on servers with multiple vulnerabilities. In a nutshell, any server regardless of Operating System, even if out of date and running with critical vulnerabilities can still be thoroughly secured without negatively impacting business. This leads us to our next topic.

Lesson #4. Know the rules—all steps of the process matter.

If you can’t describe what you are doing as a process, you don’t know what you’re doing.” 

-W. Edwards Deming

This lesson comes from one of the first national competitions where the team placed very strongly in second place. The distance between first and second place was measured in milliseconds. Many of the other teams in the final round had what I referred to as ringers. While our students were all in associate and bachelor’s degree programs, other teams fielded students who were not only in graduate-level degree programs but who often worked full-time in IT/IS already. These teams have stronger technical acuity and can sprint harder during these timed competitions.

Leading up to the competition, our coaches reviewed all the documentation on how the events would be scored. After all, this is still a game, despite the attempts to emulate real-world security events.  All sections were covered for review, including a new section. The judges would quiz each team on the Change Management Process in this new scoring section. While change management is an important aspect of any information security program, it doesn’t have the flashy appeal that battling an active adversary does—blocking and tackling matters. We took the time to teach the Change Management Process to the team thoroughly.

During the competition, our team took some lumps in the first round. We were back in the pack. Later in the day, while one team was in the hot seats taking on the Red Team, the other teams were quizzed on Change Management. Our team responded well to the quiz and took 1st place in that aspect of the competition. They leapfrogged their way to the final four. During the live finale, the team came up just milliseconds short of taking first place. Without the preparation of all security processes and not just focusing on active defense, the team delivered an overall strong security performance. In the end, this is the overall goal to begin with. This is something that many companies need to emulate—all steps in the information security process matter. Oh, and the team got their due when they returned in 2022 and won the competition, besting 1100 other national teams. This leads us to our final topic.

Lesson #5.  Microsoft Defender is actually really good at what it does.

Microsoft is not about greed. It’s about innovation and fairness.” 

–Bill Gates

I remember when Microsoft Defender Antivirus, formally known as Microsoft Defender for Endpoint, formally known as Microsoft Defender Advanced Threat Protection, formally known as Microsoft Defender, formally known as Windows Defender Antivirus, formally known as Windows Defender, formally known as Microsoft AntiSpyWare, first debuted. I was at Microsoft Tech ED 2008 in Orlando. I sat in on a couple of presentations of what the developers were trying to do with the product. It wasn’t just a Symantec knockoff.  It was original from the ground up.

Fast forward 15 years later. As previously mentioned, during the first stages of the competition, the Red Team gets access to the network to plant their tools and handicap the students. During one round, all the Windows servers (2012 and newer) had Defender disabled and sabotaged to prevent it from running during the competition. During the daily debrief, the captain of the Red Team talks about their observations. When asked about Defender, he admitted that the Red Team intentionally gutted Defender. “If we had let it run, most of our tools wouldn’t work.” That strongly indicates how good this “out of the box” security product is. It drives Red Teams to sabotage it to achieve their objectives. The Offensive Security Team at SecurIT360 highly regards this product in their testing.

Don’t take their word for it. Check out this blog referred to as “Last Antivirus Standing”. Java Exploit Code Obfuscation and Antivirus Bypass/Evasion (CVE-2012-4681) (  The author took an 8-year-old JavaScript virus and in minutes, made the most subtle tweaks to get it past 43 of 44 antivirus engines with relative ease. The lone antivirus that detected the virus during every mutation was Microsoft Defender. Long story short, Microsoft Defender is a good, solid security solution, especially for those with smaller budgets. Anyone telling you that Microsoft Defender is garbage is either financially incentivized to tell you something different or doesn’t know what they are discussing—most of the best Red Teamers out their respect Defender as a good defensive tool. The facts are there. I was fortunate to see it put through testing that most people don’t. Leveling the playing field against offensive adversaries seems like a pretty fair move to me. Thanks, Bill, and company.

Wrapping up

Teaching and coaching cybersecurity has been enlightening and rewarding. Although the victories were celebrated, watching the students grow in skill and confidence was the true honor. As mentioned, I was fortunate enough to have the opportunity to witness firsthand the battles waged by a Collegiate Cyber Defense Team against some of the country’s best Red Teams. Lessons gleaned from those clashes were shared here in hopes of helping others who are on the frontlines of today’s cyber battlefields defend themselves. Our program succeeded on a wafer-thin budget compared to competing schools with 10x to 30x the resources. The lessons shared here show how any company, even those facing the same fiscal challenges, can improve security, one small step at a time.

And yes, the tears of Red Teamers are delicious, even if they are very short-lived.

SecurIT360 is an independent, vendor-agnostic technology company focused on developing programs and systems specifically catered to our client’s needs. While some vendors are listed here, we work with each customer and their selected IT solutions on a custom basis and not “one-size fits all” approach.

* In the context of cybersecurity, a “Red Team” is a group that pretends to be an enemy. A “Blue Team” is a term for cybersecurity team who are responsible for defending networks and computers against attack.   Red team – Wikipedia.