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.

Signs of insufficient networking knowledge

Scenario 1
Phone VLAN on a switch and cross connected into a Firebox with desk phones, PCs, and printers in the environment
Questions we actually got:
On Monday, we send over the list of what switch ports are for printers, which are for PCs, and which are for desk phones. Technician says that two of the three phones are not working. We use our awesome switches to find out exactly where these other phones were plugged in. The phones were plugged into the wrong switch ports. Move desk phones, phones work.
Then later, the technician runs a test for the VOIP service from a PC on the PC VLAN not from a PC connected to the phone VLAN. So the test for the VOIP service fails. Security zone profiles exist. It is not acceptable to have an allow everything network security posture. Configures needed to support desk phones are completely different from those that are required to support domain joined Windows computer assets.
 
Some ITSPs have to pay for expensive add-ons like Auvik to try to compensate for the fact that they have inadequate switching equipment with inadequate design and a sprawl that they have to inventory and keep track of. TCO comes from how much time it takes to maintain, manage, adds/moves/deletes/upgrades, troubleshoot. If I have to physically go to a site to chase some cabling, something is really wrong.
The technician in this scenario also could not believe we wanted two network cables between the switch and core router. They are not the only one. I encountered this lack of vision of understanding in another client IT director earlier in the year. If you don't know why you would have two network cables between a switch and a core router, go figure that out.
Scenario 1
Phone system with desk phones. Each desk phone has its own network cable, which is good. Phone subnet should be a separate VLAN, but the choice is made by ITSP to separate the phones using physically separate switching equipment. That is something I would never do.
Commentary provided by ITSP:
I don’t like VLANs. I would rather setup a network with physical segmentation. Results in:
Loss of visibility
Loss of network resiliency
More expensive because you have more switches to babysit and troubleshoot
So if you have 20 or 40 VLANs, so does that mean you are going to have 20 or 40 physical switches?
If you don’t have 20 VLANs then what network security do you really have?
How do you present virtual servers on the proper microsegmented security zone when you cannot transmit tagged packets?
Let’s just talk minimum VLANs that we typically see here:
SwitchOOBM
ServerOOBM
SwitchMgmt
WAPMgmt
Phone
Surveillance
CorpWired
CorpWireless
GuestWireless
HVAC
ElecMon
Chromebooks
CaptivePortal
Tier0
DCs
AppGroup1
AppGroup2
DeprecatedApps
Printer
Storage
IAM
RMM
Clearly anything over two becomes ridiculous to do with physically separate switch equipment. The days of this paradigm or strategy are long gone since cybersecurity compliance is requiring microsegmentation. And network security strategies and technical controls are some of the most effective primary and compensating controls for cybersecurity posture for all the protected assets regardless of type.