The Real Skinny on Penetration Testing: Debunking the Myths

Welcome to Breakfast Bytes with Felicia King. Today, we delve deep into the often-misunderstood realm of penetration testing. As business owners grapple with the necessity and costs associated with these tests, Felicia demystifies the process, drawing from her three decades of cybersecurity expertise.
In this episode, discover why traditional penetration testing might just be a costly theater act and learn the importance of continuous vulnerability assessments. Felicia shares compelling anecdotes and practical advice on how to genuinely safeguard your business without burning through your budget.
Join us as we explore the intricate dance between IT teams, automated tools, and the critical decisions that can make or break your company's security posture. This is not just another tech talk; it’s a narrative that could redefine how you view cybersecurity investments.
 
 
Quick recap
 
Felicia emphasized the importance of understanding the objectives of the test, and cautioned against overpaying for tests that may not be necessary or effectively scoped.
 
Next steps
• IT team to implement continuous vulnerability assessment and penetration testing platforms for regular, automated security checks.
• CTO/CSO to assess and oversee the implementation of security tools like Tenable One and Senteon for secure configuration management.
• Executive management team to allocate budget and provide support for IT department/MSP to implement necessary security changes and tools.
 
Summary
Test Scope and IT Consultancy Management
Felicia also advised that the test should be scoped correctly and conducted by the IT consultancy that manages the company's networks, servers, and applications. She cautioned against overpaying for tests that may not be necessary or effectively scoped.
 
External Testing Approach and Cots Definition
She argued that the approach of bringing in an external third party to conduct a test without proper consultation and scope can lead to incorrect results. She emphasized that this approach would be more effective in identifying and addressing vulnerabilities, and would provide demonstrable results. Felicia also clarified the term 'COTS' as defined by the National Institute of Standards and Technology in the context of information security technology.
 
Enhancing IT Configuration for Business Acquisition
She argues that this approach provides more meaningful and actionable information, enabling IT configuration personnel to effectively address identified gaps. Felicia also highlights the importance of using recognized and professional tools like Tenable One and Senteon for secure configuration management. She emphasizes that this approach offers a better return on security investment and is more beneficial for businesses seeking to be acquired.
 
IT Testing and Business Decision Makers' Guidance
She suggests that business decision makers should provide clear direction and funding for IT before such tests are conducted.
 

Incident response and mitigating supply chain attacks

In this episode of Breakfast Bytes with Felicia King, we navigate the complex but crucial realm of cyber security. We explore the emerging menace of supply chain attacks and underscore the vital need for proactive incident response planning. Felicia reveals the staggering average cost of a cyber-attack, per employee and endpoint, and explains why smaller businesses might suffer even greater losses.
King sheds light on the often unnoticed aspect of incident response planning: the critical period between discovering a potential compromise and confirming a successful attack. She also scrutinizes the implications and expenses of in-house response strategies for sizable businesses and outlines how smaller establishments could face heftier costs.
Offering valuable advice, Felicia provides business-centric recommendations on methods of dealing with a reported incident. She addresses important issues such as identifying data breaches and managing downtime during a crisis, stressing the importance of having a contingency plan for extended recovery periods.
Moving on to supply chain risks, King critiques the increasing trend of outsourcing in the IT sector. She cautions against granting upstream providers unrestricted access to systems, noting counterparty risk as an area demanding heightened vigilance. Deeper discussions on access control, audit logs, automated compliance reporting, and other factors in selecting an efficient identity and access management system also unfold.
King further navigates the topic of APIs - the lifeblood of numerous industrial integrations - offering crucial insights into associated risks. She concludes with a call for a mindset shift required to tackle supply chain attacks effectively.
In contemporary threat landscapes, relying solely on the cybersecurity kill chain is a losing battle. This episode underscores the need for encompassing multiple defensive strategies for cybersecurity, such as multi-factor authentication, and conditional access for all accounts. Real-time analytics, endpoint protection strategies, and a zero-trust posture are championed as critical for preventing malicious activities and providing swift threat responses.
We delve into the pros and cons of network layer security, a powerful yet complex technique requiring specific expertise. When appropriately utilized, it presents a scalable solution managing traffic filtering and robust protection from supply chain attacks. The episode concludes with the importance of having a solid incident response plan as a vital proactivity measure in cybersecurity.

Methods to prevent business email compromise

Tech E&O and cyber insurance with Joe Brunsman

Tech E&O and Cyber insurance with:
Joe Brunsman of The Brunsgroup – Expert on Tech E&O and Cyber Insurance
YouTube channel – Joseph Brunsman
https://www.youtube.com/@JosephBrunsman
https://www.thebrunsgroup.com/
Damage Control book
https://www.thebrunsgroup.com/book2
Tech E&O and cyber
MSP should have a tech E&O policy. They cover different things. What types of third-party claims will they cover? A guy on the Que recently said that he did not think that E&O was required because his customers have never asked for it. You must have a TECH E&O policy.
What is the biggest thing that you need to pay attention into the E&O policy?
Look at the definition of technology services in the policy. Everything past that point, it does not matter if the definition of technology services is correct.
Avoid the named peril policy. An all risks policy is better. These are becoming harder to come by.
Named peril:  Technology services means:   there is a list
You have to prove to the insurance company that what you did falls within that definition.
What do you need to look for? “Including but not limited to”  contra proferentem = ambiguity is held against the draftsman. The onus is on the insurance company to prove that what you did was not covered under the definition.
How much coverage in the policy should they have?
How much cyber insurance do you need? Here are the variables that I think about. – See Youtube video
Brokers – There is no legal requirement that they understand or read the insurance policies.
Average IQ of an insurance broker is 104. They do not understand what they are selling. The onus is on the business owner to ask and to get the right things.
What is your major loss event? What are we worried about? Is that even possible to insure for those issues?
Step 1: Stop relying on the insurance broker.
Step 2: Fellow decision-makers in the business, what are you worried about? Talk to the broker about that. Then the broker finds “these are the options in the cyberinsurance market that address those concerns”.
Joe: Huge proponent of defense in depth over cyber insurance. Rank order the biggest bang for the buck. Felicia has been talking about that for years and is doing a webinar on 2/9/2023 on that very topic.
Insights from plaintiff’s attorney
Joe had a great convo with a plaintiff’s attorney and got his opinion on risk management.
Risk discovery question: What is the one thing that sinks the ship in the lawsuit?
There is an internal email. You knew you were supposed to do this. But they said it was too expensive. They were not going to do that. They understood the risk and just accepted it.
What could the business do in order to circumvent that email being a death blow in the lawsuit?
Plan of implementation.
No business has unlimited resources. No business is perfectly secure. You sit down the with business owners and MSP. We need to work on a plan to better your security. You don’t have unlimited money. I am a business owner too. You need a roadmap. Everyone signs off on it. We were trying, we were getting there.
Felicia: Wow this is astonishing because this is what we have been doing with clients for 20 years. It is the type of thing that a CISO knows how to do, but few others know how to do well.
 
 
Life hack tip from Joe:
Convo with the average business owner:
Obviously you are really good at what you do. You have built this business. Build a relationship with them. The MSP is not the subject matter expert on the client’s industry. Fluff their feathers. Transition that. I asked you a bunch of questions, thank you for hearing me. Now we are going to go through this. Can we just do the same thing in reverse? If you do not understand this yet, let me know and let’s break it down.
 
Joe and Felicia agree:
One way or another, those controls will be implemented. Read any breach notification letter. Magically we found more money to invest in cybersecurity.
Either work on your information security program monthly at a pace that your budget can absorb, or that decision of timing and magnitude will be taken away from you.

Dark web monitoring and avoiding FUD decisions

Kathy Durfee – CEO & Founder of Tech House joined Felicia to discuss dark web breach monitoring
Scenario: FUD report from a competitor
Perceived: Multiple users in their environment were breached. Perceived proof was report with the listing of the users and the passwords and columns that the customers did not know what that data was.
Good: Customer told their current IT service provider about the report.
FUD – Fear, Uncertainty, and Doubt – is, in the wrong hands, a powerful tool to drive snap decisions within a company. However, it is not a viable or valid sales tactic: for all it could potentially do well, causing unnecessary stress and suffering is what it does best. Speaking with Kathy Durfee, CEO and Founder of TechHouse, a managed services and solutions provider based in Florida, we walk through a recent case of FUD with a customer of hers that received a worrisome report from a potential competitor. During our chat, we covered:
The key aspects of FUD (and how it does not work)
What the Dark Web is, and the logistics of monitoring and combating it
Leadership training and best practices for helping a team best meet their security and regulation requirements
Identifying the key differences between commodified and relational partnerships, especially in the technological sphere
Shared responsibility between MSPs, their customers, and those customers’ clients
Where does dark web monitoring and dark web data risk reside on the continuum of risk? How best to mitigate?
What really is the risk and the mitigation?
Put the efforts into prevention.
Put the individual in the driver’s seat of managing the risk that is best managed by them by putting the right tools in their hands.
Resources
https://haveibeenpwned.com/
Perception of the proper allocation of the budget
Businesses must make time for training.
ITSP must include in service catalog what the client is getting in terms of services.
What do we need to do? Cross reference on tools that accomplish outcomes and cover risk mitigation and ensure that the client understands what those are.
Training is how you squeeze the juice out of the orange. Without it you may not get all the juice out of the orange or get any juice out of it at all.
Common business objections to allocating time for training
Payroll costs, but avoiding training is not legally defensible anymore.
Policies
The IT Service provider CANNOT alone write policies for you, and they CANNOT approve and enforce your organizational policies.
Four pillars
Policies
Technical controls implemented
Automation of technical controls
Reported to the business – It’s YOUR report, your organization.Shared responsibility – some months the CFO does it, some months the CEO does it.Set a schedule and do it. 3 weeks any habit; trainer or partner
Do you look at your P&L and balance sheet every month? You should be understanding the reports from IT.
 
An interesting lawyer opinion on the topic:
https://abovethelaw.com/2023/01/dark-web-monitoring-for-law-firms-is-it-worthwhile/

The relationship between proper data handling and real risk reduction

Those who listened to the November 19th, 2022 podcast I did with breach attorney Spencer Pollock know that he stated that 90% of the breaches he was involved in over the prior 12-month period would have been non-reportable had the data been properly encrypted.
https://qpcsecurity.podbean.com/e/what-you-must-do-in-order-to-prepare-for-a-breach/
(Review link above for attestation and regulatory enforcement proof.)
I have three major points for you in this show.
You need an IRP
You need a CvCISO
And you need to understand how data is being handled in your organization
Let’s first talk about CvCISO
Help you understand why you need a CvCISO working with you on a regular basis because even if you are a really large organization, the probability that all of your processes are clean, secured, compliant, and all your end user training is effective, well that probability is not high.
https://qpcsecurity.podbean.com/e/understanding-vciso-services-and-why-you-need-them/
Incident response plan
Virtually every organization is now required to have a written incident response plan. These are some examples of people that must be specifically listed in the IRP. What does your organization do when they don’t have these people as full-time internal staff? You need a CvCISO.
People you are required to name explicitly as part of your incident response plan:
IT technical staff
Incident response manager (this better be a CvCISO or a certified incident response company)
IT director
CIO
Stakeholders such as board of directors and heads of business units
Finance director
Communications manager – this is either your internal PR person, your internal corporate counsel, or your breach attorney
Legal representative – either your internal corporate counsel or breach attorney
Human resource manager
Types of data
Let’s talk about some real-world examples of data insecurity. Let’s start by establishing what some categories of data are. PII, PHI, PCI data.
PHI is personal health information so think of that as drug screening results as well as medical records. So it’s not just healthcare organizations that have it. Anyone who does drug screening will have PHI.
PII is personally identifiable information such as your name, contact information, social security number, I-9 information, a copy of your passport or driver’s license, and non-public photos of you. This is also your direct deposit bank information. I would also include your salary at your job is PII. It is certainly non‑public. So who has that kind of information on you? Well anyone who does HR recruiting or has employees is typically going to have this kind of data.
I encourage small businesses to use a PEO and not store any of this data themselves. They should outsource that entirely. Some HR management firms have areas in their SaaS platform that their customers (your employer) can upload documents to and store them securely and NOT on the employer’s environment anywhere.
PCI is payment card information. If an organization processes credit cards in any way outside of a contained e-commerce and merchant processing platform, then they probably have PCI data that is on a system they control. Many retailers just use SaaS apps that directly integrate with merchant processing to avoid any storage or holding of PCI data. You should expect that larger organizations are retaining your credit card information.
Applicant tracking and employee onboarding systems
The security of these systems is only as good as the security of the company that is using them, their processes, how they handle the data throughout the flow, and how documents you complete for them are disposed of if they were submitted in paper format.
Good process
As you interact with the recruiter or prospective employer, all of the data goes directly into an applicant tracking system that is SaaS by the applicant themselves. The only thing that may be emailed would be a resume. Any assessment results or applicant data is all direct input into the ATS. The ATS is SaaS cloud hosted with a very secure company and all accounts which access the data are on a need to know, RBAC approach with MFA enforcement.
WOTC information is all submitted by you directly into the WOTC company website
All of your PII would be submitted by you directly into the HR enrollment/payroll system without intervention from anyone else. No one else needs to handle your data.
The data you submit is only being submitted to a high security SaaS HR management/payroll platform.
Your employer never needs to download and retain any of that information because it is stored in the HR management system. Nor did your employer ever need to have a copy of the information you submitted because you submitted it yourself. So you know it is not in their email or on their servers anywhere. They also did not print it and then not shred it.
Bad process
You are an applicant and the company you are applying to has you fill out paper forms. You do and then they scan those forms with a scanner and send those files somewhere. Let’s say they are scanned to an insecure location on the internal network. Then someone retrieves the scanned images of the paper you filled out and emails them to a distribution list.
So let’s go over what is in the scanned PDF file that got emailed to an internal company distribution list.
Direct deposit information – full banking account and routing number
Full name and address
I-9 verification which includes social security number, driver’s license number, and birth certificate
W-4 which contains PII and SSN again
Copies of your signature
Date of birth
Your offer letter including salary and benefits
Concerns
What happened to the physical paper copies of the forms you completed? Were these shredded same day?
Was the information in the email distribution list forwarded to anyone who did not have a complete need to know?
Was the information forwarded to a party external to the company?
Document management platforms
Premise databases often have a lack of encryption
Lack of data encrypted at rest and quite possibly the data is not encrypted in transit. If the system that the data is stored inside of is a premise-based thick client application such as an application that has SQL server as the back end, it is not likely that those communications between the thick client and the database server are encrypted in transit. The SQL server most assuredly is not encrypted because very few applications support SQL database encryption and even fewer IT people know how to set it up.
I have seen document management platforms with 500,000 records in them containing some of the most sensitive PII and this data was not only housed on servers that were unpatchable and fully deprecated, but the data being transmitted to/from the server was not encrypted, nor was the data in the database encrypted at rest.
If you put a dollar figure to the cost of a breach and it is associated with the number of unique records that contain reportable information, the cost of that old, insecure server just went through the roof.
Even if you say $1/record, that is $500k. Wowzers! And it’s not likely that was the only server compromised in the breach.
What data is stored in people’s emails when a company does not have solid policies, end user training, and technical enforcements to prevent the data from being improperly stored?

Information Security, Cybersecurity, and Everyone’s Responsibility

What is information security versus cybersecurity?
What are policies and why do we care?
Isn't that IT's problem?
Examples to learn from

Business Email Compromise

Ken Dwight is “The Virus Doctor” – Business consultant and advisor to IT service providers and internal IT at many businesses who have come to him for his training, has his own direct clients. Ken conducts a monthly community meetings for alumni. He provides a list of curated items of current interest for discussion and resources, and has a featured topic which often includes another speaker to provide breadth of perspective. He has been doing this community service for 83 months!
I asked Ken to cover with me some topics that from his perspective don’t get talked about enough.
Business Email Compromise
Also known as CEO fraud. Impersonating a CEO for purposes of wire fraud. We are focused on the technological solutions. There is no technological solution for eliminating BEC.
CEOs must be part of the solution.
Example: Subcontractor to Airbus. Used to dealing with multi-million-dollar wire transfers.
BEC is a large Fortune 500 issue, it scales down to one user environments.
Title companies are a big target.
Retention policies and standards for WHERE to store what kinds of data to make sure that email is not a file server thereby increasing the risk of what data is compromised as part of BEC.
Perfect example of the beginning of an incident response plan or a tabletop exercise. Orgs must define the cost of compromise. That plan needs to be in place long before. It makes a recovery so much more straightforward.
Attackers analyze their victims in tiers. Potential victims $10 - $50mm revenue organizations. Reputational damage, but not big enough to have an adequate cybersecurity budget.
ShadowIT is a problem, which is why you must address it with a CFO-enforced procurement policy.
Proactive management of M365 tenant security configuration is so critical
The security of your tenant is not included in the fee for biz premium or the overall licensing.
How much activity there is, changes, products, services, vendors. Ideal stack, layers, point solutions within that. Revisit that in a period of time like a year.
This is a nice resource for M365 security and BEC.
https://www.blumira.com/office-365-security-issues
Direct advice from Ken
One topic I believe falls directly into this category is the issue of Business Email Compromise, as opposed to actual malware / hacking / ransomware attacks. As you know, the losses to BEC still represent a greater dollar value than ransomware, according to the FBI statistics. But BEC isn’t even a technology problem, it’s pure social engineering – and no additional layers of hardware or software “solutions” will prevent it or reduce the cost to its victims. In my opinion, that’s why you hear so little on the subject from the cybersecurity vendors.
Another topic I find interesting, but haven’t really heard any vendors or industry pundits talk about, is the whole new ecosystem and infrastructure produced by modern threat actors. The whole business model of these sophisticated criminals has created occupations, titles, and job descriptions that didn’t exist a few years ago. Some of these are a result of the specialization, compartmentalization, and outsourcing by these organizations; here are a few that come to mind:
Breach attorney
Ransomware Negotiator
Initial Access Broker
Cloud Access Security Broker
Multiple “As-a-Service” offerings:
Ransomware as a Service
Phishing as a Service
C2 as a Service
Another area that is mentioned fairly frequently, but typically fueled by more heat than light – and raised as a point of frustration by MSPs and IT Solution Providers in general – is the users who still believe they don’t have to worry about cybersecurity, hackers, malware, or ransomware, because they “don’t have anything the criminals would want,” or words to that effect. I believe those users need to comprehend how real and serious the threats are to their business.
By defining the multiple tiers of threat actors, the threat vectors they may employ, their potential victims, the assets owned and managed by those victims, and the attacker’s strategy for monetizing those assets, I believe it becomes obvious that every organization and every individual is the intended target of some subset of those threat actors.
Visit this resource for help making argumentation. Ken is working on some additional materials for end user cybersecurity awareness training.
https://qpcsecurity.podbean.com/e/the-real-reason-you-cannot-afford-to-have-a-cybersecurity-incident/
 

The REAL reason you cannot afford to have a cybersecurity incident

I have been thinking for months about the latest challenges faced by organizations with regards to the increased cybersecurity risks, what is at stake, how unprepared they are, and how the cyber insurance companies are responding to the changing landscape.
As I have had conversations with business decisions makers, they often think that they have little to risk. Many businesses feel that they are not under much if any regulatory framework that requires them to take action. It seems that each week I see another cybersecurity insurance risk assessment questionnaire that nearly every organization will fail. Compliance frameworks are incomplete and horrifically confusing.
There is no compliance framework that will get you the fundamentals. There is no security control framework that tells you how to have effective network layer security. The gap between guidance and successful execution is wide.
It occurs to me that the only real defense for small and medium businesses are organizations like QPC which have virtual information security officers and full remediation services on offer backed by ongoing management. There are plenty of penetration testers or those that will sell you MDR services. Execution of fundamentals is where it is at. There is little value in pursuing the frameworks until you have addressed the fundamentals. After you have the fundamentals in place, then review your status against frameworks and you will probably find that many items have already been addressed.
Regardless, I'm always on the hunt for helping the SMB organization leader. It occurs to me that no matter what data you think you have a risk or don't at risk, there is one thing you don't have which is at risk. Listen to the show to find out the real reason you cannot afford to have a cybersecurity incident.
Updated on 8/8/2021I saw this great article today on this topic and decided to include it.
The Disturbing Facts About Small Businesses That Get Hacked
I will warn that their documented risk mitigations measures are H.S.
 
And check out this excellent article on more reasons why you cannot afford to be hacked.
10 Terrifying Cybersecurity Stats | Cybersecurity | CompTIA