What is ScubaGear? The Cybersecurity and Infrastructure Security Agency (CISA) has published a hardening baseline for Microsoft 365 called ScubaGear . It’s not a whitepaper or a conceptual checklist. ScubaGear is a tactical set of configuration checks designed to help organizations secure Microsoft 365 tenants against real threats. It includes tools to run assessments, generate a score, and take action. ScubaGear helps MSPs and security teams align their configuration with a credible standard built specifically for cloud productivity environments. Why CISA’s Voice Matters CISA is the U.S. federal agency tasked with protecting national infrastructure from cyber threats. They created Shields Up, KEV alerts, and other trusted frameworks used across both the public and private sector. CISA does not sell licenses or products. Their guidance is threat-informed and purpose-built to reduce risk. For MSPs, this makes ScubaGear a rare tool — one that provides external validation and a defensible baseline to anchor client conversations and justify action. Why Secure Score Isn’t Enough Microsoft’s Secure Score is widely known but inherently limited. It attempts to balance security with usability, licensing tiers, and product promotion. Some recommendations require premium SKUs, while others include tradeoffs that Microsoft leaves up to the user. ScubaGear flips that lens. It assumes the tenant is a target and applies a security-first posture. Its assessments are pass or fail — not partial credit — and focused purely on risk reduction. Secure Score gives you a number. ScubaGear gives you a defensible answer. Why This Matters Now Microsoft 365 is everywhere. Over 345 million users rely on it every day, and attackers know it. Despite improvements, many tenants remain misconfigured — often due to defaults, old policies, or unclear responsibility. 82% of breaches  involve the human element (Verizon DBIR 2024) Only 26% of SMBs  enforce MFA across all cloud services (Datto SMB Security Report) More than 80% of tenants  still have legacy authentication enabled (Proofpoint Cloud Threat Report) ScubaGear provides structure and clarity to help reduce these risks. How to Use ScubaGear You can get started right away: Read the Baseline. Explore the ScubaGear GitHub repository  to view the full list of configuration controls. The baseline is published in both JSON and readable formats. Run the Assessment. Use CISA’s official PowerShell script to assess a tenant. The script will produce a score out of 100 and list which controls passed or failed. Results can be exported in JSON or CSV format for reporting. Review the Score and Findings. Start by focusing on the failed controls. These are real, actionable risks and often quick to fix. Here’s an example of what a finding looks like: Control ID: SCB-002   Name: Enable Mailbox Audit Logging Result: FAIL Recommendation: Run 'Set-Mailbox -AuditEnabled $true' for all user mailboxes Risk: Without audit logging, suspicious activity may go undetected These findings are practical and concrete. You can fix many of them in minutes. Educate Clients. Use the results as part of onboarding, QBRs, or monthly service reporting. They help explain why changes are needed and show that you are following a national-level security framework. Final Thought Most Microsoft 365 tenants still contain hidden risks. Even when MFA is in place, it’s common to find: Legacy authentication still allowed Audit logging turned off Insecure guest sharing Admin roles with excessive permissions If you manage Microsoft 365 tenants, this is worth your attention. Next Steps: From One-Off Assessment to Scalable Practice Running ScubaGear manually is a strong start. But managing dozens of tenants, detecting configuration drift, and responding to findings at scale takes more than scripts and spreadsheets. That’s where solutions like ThreatMate  step in. We help MSPs automate ScubaGear assessments, monitor configuration changes over time, and provide a centralized view across all clients. More on that soon! Learn more on threatmate.com

And what every MSP should know before their clients get hit Microsoft 365 is the crown jewel for attackers Microsoft 365 has become the backbone of modern business. For small and mid-sized organizations, it powers everything from email and file storage to authentication, collaboration, and business continuity. That also makes it one of the most targeted platforms on the internet. Compromising a Microsoft 365 account can mean access to sensitive data, client communications, financial records, and administrative controls. It is a one-stop shop for attackers. Did you know?  Over 345 million people use Microsoft 365 globally, and nearly 90 percent of cyberattacks begin with email or identity compromise.  (Source: Microsoft Security Blog) Most tenants are still exposed Despite Microsoft 365’s importance, many environments are dangerously undersecured. Default settings are often left unchanged, and critical protections are either misconfigured or completely missing. Here are just a few of the most common exposures we still see in the field: Legacy authentication is still enabled , allowing attackers to bypass MFA entirely Admin accounts lack MFA , even when those accounts can reset passwords, change permissions, or access sensitive data Audit logging is turned off , which means no trail to follow after an incident External sharing is unrestricted , making it easy for data to leak out without anyone noticing Auto-forwarding rules  silently send emails to attacker-controlled mailboxes, often used in BEC scams These risks are rarely intentional. They happen because M365 tenants are complex and constantly evolving. But when something goes wrong, your clients won’t care if it was a default setting or a missed checkbox. They will care that a breach occurred and that it could have been prevented. Now’s the time to ask:  Do your clients still allow basic auth? Do they have MFA on every privileged account? Are audit logs are turned on in case you need to look into something? This is hard to scale For MSPs, auditing Microsoft 365 environments is time-consuming and inconsistent. Each tenant is unique, tools are fragmented, and recommendations often vary by license level or personal opinion. Microsoft Secure Score offers some visibility, but it blends security advice with usability and sales priorities. Many MSPs are left guessing what "good enough" really looks like. What defines secure? This is the core challenge. What do you measure your clients against? What configuration is good, what is risky, and what is overkill? Secure Score gives you a number, but not always a clear standard and often feels like an upsell to another license. CIS Benchmarks are helpful, but often feel abstract or too generic. MSPs need something actionable. Something credible. Something that is based on how real attacks happen, not just what licenses are available. A real baseline has finally arrived The Cybersecurity and Infrastructure Security Agency (CISA) released something MSPs have needed for years: a tactical, credible security baseline for Microsoft 365. It is called ScubaGear . And it is not a whitepaper. ScubaGear is a set of tactical, specific configuration checks built to help public and private organizations secure their Microsoft 365 tenants against real-world threats. It includes: A detailed configuration checklist A scoring system from 0 to 100 A free PowerShell script to run assessments JSON output you can integrate or report on This isn’t theoretical guidance - it’s field-tested, operational, and aligned with national cloud security expectations. CISA doesn’t sell software. They build frameworks based on how attackers work, not what vendors want to sell. For MSPs, ScubaGear is the clearest standard yet to assess risk, align with regulators, and drive remediation efforts with real authority. Up next: breaking down the ScubaGear baseline In our next post, we will walk through what ScubaGear actually checks, how to run it yourself, and how you can use those findings to protect your clients. We will also show how ThreatMate helps MSPs take this from a one-time assessment to an ongoing service that runs across all tenants, tracks drift, and keeps configurations aligned with CISA’s guidance. If you manage Microsoft 365 tenants, this is something worth your time. Schedule a a free Security Baseline for your Microsoft 365 tenants.

Listen to the podcast #CyberSecurity #MSP #AI #Ransomware #ThreatIntelligence #Automation #PenTesting #AIPentesting #Pentest #LeftofBoom The cyber game just changed. A hacker recently leveraged Anthropic’s Claude AI, more specifically its coding assistant, to launch a ransomware campaign against 17 organizations , ranging from healthcare and government agencies to religious institutions. What made this incident different wasn’t just the breadth of targets; it was the method of using AI to upskill, automate and scale. Instead of painstakingly writing exploits or relying on years of technical expertise, the attacker turned to AI to automate the entire process. Reconnaissance, vulnerability scanning, credential harvesting, lateral movement, and data exfiltration were all handled with the help of Claude. The AI didn’t stop there. It also drafted ransom notes that were psychologically manipulative and tailored to each victim, and it calculated ransom demands based on financial data—ranging anywhere from $75,000 to $500,000. This new style of hacking, dubbed “vibe coding,” demonstrates that almost anyone—not just elite operators or nation-states—can now carry out complex, multi-stage attacks with the assistance of AI. The Rise of AI-Enabled Cybercrime The Anthropic case is a stark reminder of how quickly the cyber landscape is shifting. The attacker used Claude AI to scan thousands of VPN endpoints and highlight potential weak spots. Once inside, the AI made both tactical and strategic decisions about what systems to prioritize and which files to steal. It didn’t just automate the mechanics of an attack, it orchestrated them, coordinating steps in a way that would normally require a team of seasoned hackers. Even the ransom demands showed the power of AI. Rather than using cookie-cutter templates, the notes were customized, visually alarming, and crafted to exert maximum pressure. By analyzing stolen financial data, the AI adjusted the ransom amounts dynamically tailored to each victim, making them creditable, actionable and difficult to ignore. In short, AI has lowered the barrier to entry for cybercrime. Operations that once demanded months of planning and technical skill can now be launched rapidly by individuals with far less expertise. This is bad news for businesses of all sizes, but particularly for SMBs who are most often the target of ransomware attacks. Why Traditional Defenses Will Fail This evolution poses a fundamental problem for defenders. Traditional security tools, firewalls, antivirus software, endpoint detection, were built to protect against human-driven attack patterns. They rely on recognizing known exploits typically fashioned after named adversaries, detecting their signature behavior patterns, and responding to established tactics, techniques and protocols (TTPs). AI-enabled attacks don’t follow those patterns. They adapt in real time, modify their strategies on the fly, can do deep research based on context and attack surface, and operate at a speed and scale that overwhelms traditional defenses. What took a hacker days or weeks to compromise can now happen in hours, and the automation means those same attacks can be replicated across dozens or even hundreds of targets. The simple truth is that legacy defenses, however reliable they’ve been in the past, were not designed to withstand AI-driven adversaries. Fighting AI With AI If attackers are using AI to innovate, adapt, and scale their operations, defenders must do the same. The future of cybersecurity lies in automation on both sides of the equation. For organizations, that means moving beyond traditional defenses and embracing AI-first defenses. And where better to start than to emulate these adversarial tactics with AI-driven pentesting ? AI-driven pentesting allows organizations to simulate the same types of adaptive, multi-stage attacks that adversaries are now running. It reveals how an AI-enabled attacker would move through a network, identifies which defenses are most likely to fail, and highlights vulnerabilities in the order they are most likely to be exploited. Armed with this knowledge, defenders can remediate exposures proactively, before the real attacks arrive. The Bottom Line The Anthropic case is a pre-view of what's to come. Hackers no longer need elite skills to wreak havoc at scale. With AI, the line between amateur and professional has blurred, and the gap between script kiddie and nation-state is closing fast. For defenders, the message could not be clearer. The tools of yesterday will not protect against the threats of tomorrow. To meet the challenge of AI-enabled adversaries, IT management must embrace automation and intelligence in their defenses. That’s where ThreatMate  comes in. Our AI-driven pentesting platform is designed to put you ahead  of the curve, simulating the same kinds of AI-enabled attacks adversaries are using—before they ever reach your client networks. By identifying and prioritizing vulnerabilities through automated mission plans, ThreatMate empowers MSPs and IT teams to shore up defenses proactively and protect more clients with less effort. The attackers are evolving. With ThreatMate, evolve faster. Evolve now by seeing ThreatMate in action.

#MSP #CyberSecurity #Pentesting #ThreatMate #AutomatedPentesting #LeftofBoom #AIPentesting For many MSPs, pentesting feels like something reserved for big enterprises with big budgets. Annual red-team exercises, thousand-page reports, and a team of specialists parachuting in for a week; this is the traditional image. But the reality today is different. Pentesting has become more accessible, more automated, and more mainstream, even for the SMB space. That means MSPs can finally bring the value of pentesting directly to their clients, without needing an army of security engineers. The real question isn’t whether  MSPs should be doing pentesting—it’s how  to make it part of your standard service delivery card. Let’s look at where pentesting fits in the MSP workflow and how it creates tangible value for clients. Pentesting for Prospecting One of the best ways to distinguish yourself from the competition is to conduct a cyber security risk assessment on prospects. You will not only prove yourself to be a competent cybersecurity first firm, but also be able to uncover any exploitable vulnerabilities the incumbent IT team has left wide open. In addition, for your own liability protection before you sign up to manage an environment, you need to know what you’re walking into. Automated pentests can surface issues—like exposed services, misconfigured Active Directory, or insecure SaaS apps—that might otherwise go unnoticed until they become a problem. Think of the environment you are assessing as the current “baseline.” Just as you’d inventory hardware and software, you should also inventory security exposures. Even better, an automated pentest provides an actual inventory of the hardware/software assets on the network so you have ground truth on what you will be managing. Presenting those findings to the prospect early demonstrates your value, sets expectations, and provides a clear roadmap for remediation. Pentesting as Part of Compliance Cycles Many SMB clients face compliance requirements—PCI DSS, HIPAA, SOC 2, or even cyber insurance questionnaires. These frameworks often require proof of security testing, and a vulnerability scan alone, while necessary, isn't sufficient. Pentesting fills that gap. By weaving pentests into quarterly or annual compliance reviews, MSPs can give clients evidence they need for auditors while also uncovering issues before they’re flagged by someone else. Done right, this becomes a recurring, billable service that positions the MSP as not just an IT provider, but a compliance partner. Pentesting for Continuous Security Validation Attackers don’t wait for annual audits, and neither should MSPs. With automated tools, pentests can be scheduled quarterly, monthly, weekly, or even daily. This transforms pentesting from a one-off exercise into an ongoing validation layer that sits alongside patch management, backup testing, and endpoint monitoring. For clients, this means they’re not relying on hope between security reviews. For MSPs, it means you’re always armed with fresh data to show your value, prioritize remediation, and keep the conversation focused on proactive security rather than firefighting. Pentesting After Major Changes or Incidents Another key use case is validation after change. Migrated a client to Microsoft 365? Rolled out a new firewall? Brought a new SaaS platform online? A pentest can confirm the changes didn’t introduce new exposures. The same goes for post-incident situations. If a client experienced a breach, or even a suspicious event, a pentest can help verify whether attackers left behind backdoors, misconfigurations, or other weak points. It’s a way to give both you and the client peace of mind. Turning Findings into Value Of course, running pentests is only half the battle. The real value comes from how MSPs present and act on the findings. This is where many traditional pentest providers fall short—they deliver dense reports, but little business context. MSPs have an opportunity to do better. By framing vulnerabilities in terms of business risk , eg, “this flaw could allow attackers to access payroll data”, rather than “CVE-2024-12345 found”—you make the results actionable. By prioritizing findings based on exploitability and client impact, you avoid overwhelming clients with a laundry list of issues. And by integrating remediation into your existing workflows, you turn pentesting from a point-in-time service into an ongoing cycle of improvement. Why Pentesting Matters for MSPs Pentesting is no longer just a compliance checkbox or an enterprise luxury. For MSPs, it’s a way to: Win trust quickly with new clients Build recurring revenue through ongoing testing Strengthen compliance offerings Prove value with clear, prioritized reporting Stay ahead of attackers by continuously validating defenses In other words, it’s a service that makes your clients safer and your business stronger. The Road Ahead This brings us full circle in our series on AI pentesting. From the origins of pentesting, to the rise of automation, to the emerging role of AI and Pentest GPT, the message is clear: pentesting isn’t going away. It’s evolving into something faster, smarter, and more MSP-friendly. The MSPs that embrace this evolution will be the ones who not only protect their clients better, but also stand out in a crowded market. Pentesting isn’t just about finding weaknesses—it’s about proving value, every single day. Ready to start on your pentesting journey? ThreatMate is here to help. Sign up for a demo today.

#pentestGPT #automatedpentesting #AIpentesting #vulnerabilitymanagement The story of pentesting has always been one of evolution. What began as infrequent, expensive human-led exercises gave way to automated testing platforms that offered repeatability and scale. Now, we’re entering a new chapter: AI-driven pentesting, powered by large language models (LLMs). At the center of this shift is what many call Pentest GPT  — the application of GPT-style models to penetration testing workflows. But what does Pentest GPT actually do in practice? How is it different from generalized AI like ChatGPT? And, importantly for MSPs, how can you tell which of these emerging tools are worth trusting? From General GPTs to Pentest GPTs It’s tempting to think of Pentest GPT as “ChatGPT with a hacker hoodie,” but the distinction matters. ChatGPT and other generalized models are trained on a broad diet of internet text. They can explain concepts, draft documentation, or brainstorm attack scenarios. But they don’t have deep knowledge of exploit frameworks, vulnerability databases, or real-world offensive security workflows by default. Pentest GPTs, on the other hand, are fine-tuned for this exact domain. They are trained on curated data sets that include CVE descriptions, red team playbooks, penetration testing reports, and MITRE ATT&CK techniques. They aren’t just answering questions in a vacuum — many of them are integrated with pentest tools like Nmap, Burp Suite, Nuclei or Metasploit, which allows them to interpret outputs and recommend next steps. The difference is practical. ChatGPT might give you a good summary of SQL injection. A Pentest GPT could actually walk you through testing a live SQL injection vulnerability, generate a payload, validate the exploit, and then draft a remediation plan for your client. Where Pentest GPT Fits in the Workflow The role of Pentest GPT is not to replace scanners or exploit frameworks, but to add intelligence between the tools. For example, it can help with reconnaissance by sifting through unstructured information like documentation or leaked credentials and highlighting what’s relevant to an attack surface. It can also assist in crafting or adapting payloads, saving pentesters the time of digging through syntax and coding nuances. Perhaps most powerfully, GPT models can plan through stages of attack like a red team would do. A traditional automated platform might tell you that a server has an outdated service and that Active Directory has some weak permissions. A Pentest GPT can connect those dots into an attack path: if exploited together, this vulnerability chain could lead to domain admin. That’s the kind of context MSPs need to turn findings into action. Finally, there’s reporting. This is where GPT shines. Pentesters have long struggled to translate deeply technical findings into business-relevant risk language. A Pentest GPT can transform “CVE-2024-12345 exploited successfully” into “Attackers could access your payroll system and exfiltrate employee data. The patch for CVE-2024-12345 on these specific machines should be applied immediately.” For MSPs trying to communicate value, that’s game-changing. Who’s Building Pentest GPTs — and Which Ones Matter Not all Pentest GPTs are created equal. Some are academic prototypes, others are experimental open-source projects, and a few are beginning to show up in commercial tools. PentestGPT , developed as a research prototype, fine-tunes GPT specifically for penetration testing workflows and has shown significant improvements over baseline GPTs in task completion. AutoPentest  is another example — built with GPT-4 and LangChain, it attempts multi-step black-box testing, including reasoning about which exploit or test to run next. PenTest++  blends generative AI with traditional automation frameworks to create a modular, more adaptable testing flow. These tools are early, but they highlight the direction the field is heading. Some vendors are also starting to embed GPT layers into broader automated pentest platforms, where the model interprets results, prioritizes risks, and even drafts reports. Evaluating Pentest GPTs: The Good, the Bad, and the Risky For MSPs considering these tools, evaluation is critical. Accuracy is the first test — does the model deliver factually correct and verifiable results, or does it hallucinate? Integration matters too: a good Pentest GPT won’t live in isolation, it will plug into the scanners, exploit frameworks, and reporting platforms you already use. Transparency is another marker: do you know what data it was trained on and how often it’s updated? Given how quickly CVEs emerge, stale training is a red flag. And then there’s security itself. If the model processes client-sensitive information, where does that data go? Is it fed into a public API, or handled in a private, secure instance? These are questions every MSP should be asking before trusting a Pentest GPT with real environments. The Role of GPT in Pentesting At its core, GPT is not a scanner, not an exploit engine, and not a silver bullet. Its real value comes in three layers: A reasoning layer  that connects outputs from multiple tools into attack narratives. An assistant layer  that guides technicians through decision points and best practices. A translation layer  that reframes technical vulnerabilities as business risks clients can understand. This makes Pentest GPT less of a replacement and more of a force multiplier. The strongest results come when GPT is paired with deterministic scanners and exploit frameworks — the AI provides reasoning and reporting, while the tools provide reliable validation. Looking Ahead Pentest GPT is still in its infancy, but the potential is clear. As models get sharper and integrations improve, MSPs will be able to offer security validation that’s not just continuous, but contextual — always tied back to real attacker behavior and client risk. The future of pentesting isn’t just more automation. It’s AI-driven pentesting , where GPT fills the gaps between scanning and exploitation, amplifies human expertise, and helps MSPs scale offensive security without losing quality. Want to get started on your pentesting journey? Download the whitepaper or set up a demo today.

The Pentester's Toolbox Listen to the podcast Pentesting isn’t just a technical exercise—it’s a craft. And like any craft, the quality of the work depends heavily on the tools in the kit. Whether you’re conducting a manual engagement, using an automated platform, or blending both approaches, the right tools can be the difference between a superficial scan and a deep, actionable security assessment. For MSPs, understanding the pentesting toolbox is essential—not just for delivering results, but for evaluating solutions, hiring security talent, and explaining to clients exactly how you’re validating their defenses. The Pentesting Workflow & Key Tools As the graphic above shows, a pentest typically moves through several stages, each with its own specialized toolset. 1. Reconnaissance & Asset Discovery The first phase is all about understanding the target environment, or taking inventory of all the devices on the network. The results from this phase can be retained in a CMDB to keep track of assets down the road. Some open source tools can be useful for this including: Nmap  – Maps networks and identifies running services Shodan  – Finds exposed devices on the internet Amass  – Uncovers subdomains and related infrastructure 2. Vulnerability Identification Here, the goal is to find potential weaknesses in the target environment by scanning the target network for vulnerabilities. The output from the vulnerability is quantification of the attack surface(s). Some common tools for this include: Nessus  – Comprehensive vulnerability scanning OpenVAS  – Open-source vulnerability management Qualys  – Cloud-based vulnerability scanning platform In addition to understanding the potential points of exposure, it is important to understand the risk, based on threat intelligence of which vulnerabilities are being actively exploited versus those which may not have an associated exploit. 3. Exploitation The next phase is where you make your money. Automated pentesting tests the attack surface found in the preceding stage to determine which of the discovered vulnerabilities can be safely exploited. This is the so-called proof in the pudding. Any exploited vulnerabilities are proof positive that an adversary would succeed to a quantifiable extent in penetrating the network. These vulnerabilities must be remediated immediately. Some common tools for pentesting include: Metasploit Framework  – Exploit development and execution SQLmap  – Automated SQL injection exploitation Responder  – Captures credentials in Windows environments 4. Post-Exploitation & Lateral Movement Once inside, the objective is to simulate attacker behavior for persistence and pivoting. This stage is for more advanced pentesters who are able to leverage that initial exploitation on a beach head machine and then find further targets of interest. A common approach is simply to repeat steps 1 through 3 from behind the firewall to find targets of opportunity and then exploit, wash, rinse repeat. A more organized approach is to begin with a target device (eg Active Directory server, back-up storage) and chain together a set of exploits and devices to get to the target machine. Some other tools that can be helpful here include: Cobalt Strike  – Adversary simulation platform Empire  – PowerShell-based post-exploitation BloodHound  – Active Directory attack path analysis 5. Web Application Testing Web application testing forms its own category of pentesting as it is often not hosted on the client network, nor is an initial entry vector, but often a target itself for the data and applications it hosts. Testing web applications is typically relatively straight forward because they exist on the internet by definition, unless it is an intranet application. Be sure to obtain permission from the prospect or client before testing any of their networking infrastructure. For web apps, APIs, and portals, some common tools that focus on application-layer vulnerabilities include: Burp Suite  – Web app proxy and scanner OWASP ZAP  – Open-source web security testing 6. Reporting & Collaboration While running all these tools are fine, the findings mean nothing without clear, actionable reporting for your client. For most SMBs, the details in the findings don't matter. What is required is easy to understand risk tables or graphs that are actionable with specific timelines, along with the impact of remediating the findings or conversely the risk of not remediating the findings. A couple of tools that may be helpful for reporting include: Dradis  – Reporting and collaboration for pentesters Faraday  – Collaborative vulnerability management platform However, be sure that your reporting program matches your QBR format for consistency. Where Automation Fits In Automated pentesting platforms like ThreatMate integrate many of these capabilities into a single, continuous process. They can handle reconnaissance, vulnerability detection, safe exploitation, and reporting without requiring the MSP to juggle multiple tools. Modern platforms including ThreatMate often include scoring systems like CVSS  and EPSS  to prioritize vulnerabilities based on real-world exploitability, helping teams focus on the most pressing risks. Why MSPs Should Care About the Toolbox You don’t need to master every tool, but you should: Understand what each category of tool does Recognize when specialized tools are required Confirm your automated pentesting platform covers all critical stages Be able to explain your process to clients in plain language Knowing your tools builds confidence—not just in your technical capability, but in your ability to protect your clients effectively and consistently. In summary, pentesting involves multiple stages and different toolsets to achieve the outcome desired for prospects and clients. This blog provides a decent overview of the tooling that is out there if you would like to do it yourself. ThreatMate provides a single platform from which you can conduct end to end pentesting and vulnerability discovery to find and fix security exposures before the bad guys exploit them. Sign up for a demo today!

Listen to the Podcast In our last post, we explored why pentesting still matters, tracing its history from human-led pentesting to the challenges of cost, consistency, and limited frequency. Now it's time to look at the next chapter — automated pentesting — and why it’s becoming the go-to approach for MSPs looking to scale their security offerings and ensure the clients they take on are not introducing risk to themselves. From Vulnerability Scanners to Automated Pentests Before we dive into automated pentesting, let’s clear up a common misconception: Pentesting is not the same as vulnerability scanning . Vulnerability scanners  (like Nessus, OpenVAS, Tenable, or Qualys) are designed to find  known weaknesses—misconfigurations, outdated software, missing patches. They are fast and useful, but they stop short of proving exploitability . Automated pentesting tools , on the other hand, take things a step further: They simulate real-world attacks Attempt to exploit vulnerabilities in a safe, controlled manner Chain multiple weaknesses together to mimic how attackers pivot inside a network Deliver prioritized findings that reflect actual business risk In short: scanning tells you what might be wrong ; automated pentesting shows you what an attacker could actually do and the resulting impact . Why Automated Pentesting Works for MSPs MSPs face a tricky balance—clients expect robust security, but margins and staffing realities mean you can’t have a human pentester on every account. Automated pentesting changes the equation. Key advantages: Frequency Without Fatigue Run tests quarterly, monthly, or even weekly without burning out your security team. Consistency Across Clients The same methodology, every time, ensures comparable results and eliminates the “human variability” factor. Scalable Service Delivery Whether you have 10 clients or 200, automated pentesting scales with your customer base. Actionable Prioritization Many pentesting platforms including ThreatMate integrate EPSS  (Exploit Prediction Scoring System) and CVSS  to sort findings by actual exploit likelihood, helping you focus on the most dangerous issues first. How Automated Pentesting Works (Under the Hood) While features vary by platform, the core workflow generally includes: Reconnaissance Mapping assets, services, and potential entry points. Vulnerability Discovery Identifying misconfigurations, outdated software, and exposed services. Exploitation Simulation Safely testing whether vulnerabilities can be exploited—and how far an attacker could go. Lateral Movement & Privilege Escalation Attempting to move deeper into the network, chaining multiple vulnerabilities together. Reporting & Remediation Guidance Delivering clear, prioritized reports your team can act on immediately. Operationalizing Automated Pentesting for MSPs Here’s how forward-thinking MSPs are integrating automated pentesting into their offerings: Prospecting Run a pentest on prospects to build out a cybersecurity risk assessment. This is a strong way to differentiate yourself, while also learning earyl what you are getting in to. Quarterly or Monthly Security Reviews Provide clients with fresh, data-backed proof of their current security posture. Incident Response Readiness Simulate attacks to validate defenses after a breach or major system change. Compliance Support Use results to satisfy PCI-DSS, HIPAA, SOC 2, and other framework requirements. The Business Case Automated pentesting isn’t just a technical upgrade—it’s a business growth engine . MSPs offering it can: Justify premium security packages Increase client retention by proving ongoing value Create upsell opportunities with remediation and consulting services Next Up: The Pentesting Toolbox In our next post, we’ll break down the essential tools—open-source and commercial—that security teams use during pentests, from reconnaissance to reporting. You’ll see how these tools fit into both manual and automated workflows. Pentesting isn’t going away—it’s becoming faster, smarter, and more scalable. MSPs that embrace automation now will be the ones leading the market tomorrow.

Watch a video of this blog Cybersecurity is no longer a nice-to-have for MSPs, it’s mission-critical for yourself and your clients. As threat actors grow more sophisticated and SMB clients face increasing pressure to meet compliance and cyber insurance requirements, one security discipline has stood the test of time: penetration testing. But not all pentests are created equal, and the way MSPs deliver this service is rapidly evolving. Let’s take a step back and understand the origins of pentesting, why it still matters today, and how it’s changing to meet the modern threat landscape. The Origins of Pentesting: A Human-Driven Craft Penetration testing has its roots in the 1960s and 70s, when early security professionals, many from military or government backgrounds, attempted to simulate how real-world attackers might compromise a system. These early efforts were manual, time-consuming, and the quality depended on the skill of the particular team doing the testing. Over the years, human-led pentesting evolved into a specialized discipline. Skilled practitioners used a combination of tools, scripting, and intuition to: Identify weaknesses in networks, applications, and endpoints Attempt to exploit those weaknesses to prove their impact Deliver detailed reports with recommendations for remediation This process remains valuable today. But for MSPs, traditional pentesting often presents a series of challenges. The Problem with Traditional Pentesting While manual pentesting provides deep insight, it comes with trade-offs: High Cost : A single manual pentest can cost thousands (or tens of thousands) of dollars. Inconsistent Quality : The outcome depends on the skill, methodology, and diligence of the human tester. Limited Scope : Human time is finite—tests are often narrow in scope and only represent a snapshot in time. Usually it is a capture-the-flag exercise vs a comprehensive assessment. Low Frequency : Most organizations only conduct tests annually or for compliance, leaving long windows of exposure. For MSPs, this model is difficult to scale across multiple clients and often leads to missed revenue opportunities or weak security coverage. Why Pentesting Is More Relevant Than Ever Despite its limitations, the concept of pentesting—simulating real attacks to validate defenses—is more vital now than ever before. Here’s why: Attackers Don’t Wait : Real-world threats evolve daily; defenses must be tested continuously. Compliance Requirements : Frameworks like SOC 2, PCI-DSS, HIPAA, and others increasingly mandate regular testing. Client Expectations : SMBs now demand proof that their IT provider is taking proactive steps to secure their environment. Insurance and Legal Exposure : A failure to validate security posture can lead to denial of cyber insurance claims or legal liability. Pentesting is not just a checkbox exercise—it’s a core validation layer in a defense-in-depth strategy. The Shift Toward Continuous, Automated Pentesting The answer for MSPs isn’t to abandon pentesting—it’s to modernize how it’s delivered. By adopting automated pentesting solutions, MSPs can: Perform assessments more frequently without breaking the bank Deliver standardized and repeatable results across clients Discover and validate vulnerabilities in real time Differentiate themselves from competitors still offering one-and-done scans This doesn’t replace human-led pentests, but it allows MSPs to offer ongoing offensive testing as part of a managed service. Coming Up Next: How Automated Pentesting Changes the Game In our next post, we’ll explore how automated pentesting tools work, how they compare to traditional vulnerability scanners, and how MSPs can operationalize them to better serve their clients. Pentesting isn’t going away—it’s evolving. And MSPs that embrace this shift will be better positioned to protect their clients, prove their value, and grow their business. To learn how you can adopt automated pentesting in your business, contact ThreatMate below.

Summary Most MSPs rely on referrals — but if you're not showing up on Google, you're invisible to prospects. Learn how to use AI tools for smarter SEO: from keyword discovery to content generation and site audits. How Tos Let’s face it — most MSP websites look fine but rank nowhere. Search engine optimization (SEO) is what brings your site traffic from people actively looking for IT support, cybersecurity, and compliance help. The good news? AI makes SEO 10x easier. Here’s how MSPs are using it to win: 🧠 Step 1: Keyword Discovery with AI Use tools like: ChatGPT + Keywords Everywhere  – Ask for keyword variations for your niche (“managed IT in Dallas” or “HIPAA compliance support”) Ubersuggest / SurferSEO  – Find real search volume, competition, and content gaps Google Search Console  – See what you already  rank for and where you’re close to top 10 💡 Pro tip:  Ask ChatGPT to “cluster” related keywords so you can build topic hubs (e.g., M365 security, phishing prevention, or data backups). ✍️ Step 2: AI-Powered Content Creation Once you know what to target: Use Jasper , ChatGPT , or Copy.ai  to write blog drafts, service pages, or FAQs Then fine-tune the tone, add local examples, and format for readability Use Grammarly  or Hemingway App  to polish the language Don't forget meta descriptions and image alt text — AI can help there too 🎯 Focus on “pain-point” keywords like: “IT support for law firms” “MFA not working” “How to fix Outlook login loop” 🛠️ Step 3: Technical SEO with AI Assistants Use Screaming Frog SEO Spider  or Ahrefs Site Audit  to find broken links, slow pages, and crawl errors Ask ChatGPT to explain complex audit findings Use AI to generate fix recommendations or even write alt tags and schema markup 📈 Track your rankings using Google Search Console , SerpRobot , or ProRankTracker 🔄 Consistency = Visibility Google rewards freshness. Even one new blog post per month (AI-assisted!) can move the needle. And if you're using help desk ticket data to drive content ideas — you're turning support into SEO fuel. You don’t need to become an SEO expert. You just need to give AI the playbook. Reach out if you want more coaching!

Summary Want to train your techs or test AI-driven hacking safely? Build your own internal pentest lab using open-source tools and simulated environments — all enhanced with AI automation. The How To Think of an AI pentest lab as your cybersecurity sandbox — a place to experiment, train, and simulate real-world attacks without touching production systems. And yes, you can build one with open-source tools. Whether you're training junior techs or exploring AI-driven offensive tooling, this guide shows MSPs how to get started: 🛠️ What You'll Need: 1. A Test Environment Use VirtualBox  or Proxmox  to spin up isolated VMs Set up vulnerable machines like Metasploitable2 , DVWA , or TryHackMe/THM labs Isolate the network or run it on a VLAN 2. Open-Source Pentest Tools Kali Linux  with tools like Nmap, Nikto, Metasploit OWASP ZAP  or Burp Suite Community  for web app testing 3. AI-Powered Assistants Use ChatGPT  or AutoGPT  to walk through attack paths, explain outputs, or generate payloads Run an LLM locally (e.g., Ollama + open-source model) to assist without internet access 4. Workflow Automation Try tools like PentestGPT , ReconGPT , or scripting with Python to automate scans and reporting 🧪 Why It Matters for MSPs: ✅ Train staff in real-world attack scenarios ✅ Test toolchains before client rollout ✅ Stay current with evolving threats Plus, you’ll be better equipped to pitch pentesting services to clients — because you’ve done the work in house . Start small. Run safe. Get smarter. If you would rather not take the time to do all this, ThreatMate has you covered. Just sign up for a time and we will walk you through AI Automated Pentesting.

Summary Client reports don't need to be painful or plain. Learn how MSPs are using AI to generate stunning, executive-ready security reports — from vulnerability summaries to patch metrics — in minutes, not hours. How to Do It As an MSP, reporting is more than a task — it's your proof of value. But let’s be honest: most security reports are either too technical, too generic, or too time-consuming to create. Enter AI. With the right tools, you can generate beautiful, customized security reports that your clients actually read — and that position you as a proactive partner, not just a vendor. Here's how MSPs are doing it: 🔧 Tools That Make It Easy: ChatGPT or Claude : Summarize scan results in plain English ThreatMate : Automatically pull findings, EPSS/CVSS scores, and affected assets into a branded report Beautiful.ai / Canva Docs : Create polished, client-ready slide decks or PDFs with charts and visuals Power BI / Looker Studio : For MSPs with larger clients, build live dashboards that pull from your tools 🧠 What ThreatMate AI Does for You: Translate vulnerability scan data into executive summaries Highlight critical issues by business impact, not just CVSS Include helpful visualizations of trends, patches applied, and open items Suggest remediation recommendations based on known fixes 📈 Pro Tip: Use ThreatMate to auto-generate a “risk scorecard” that tracks the client’s security health quarter-over-quarter. Clients love seeing progress (and risk reduction) in a visual format. Don’t just report data. Tell a story  — one where your MSP is the hero keeping them secure. Schedule a Demo today!

#AIhelpdesk #digitalworkers #AIchatbots Summary MSPs can use AI chatbots to handle routine tickets — password resets, printer issues, onboarding guides — and slash response times. This post shows how to build one using Microsoft Copilot, ChatGPT, or Tidio. Power Up Your Techs The average MSP help desk drowns in routine tickets. AI can handle the boring stuff — and free your team to focus on what matters -- supporting your clients' business goals. Start with these quick wins: Password resets (auto-email responses with links) Printer troubleshooting (flowchart-style AI answers) Onboarding checklists (auto-generated from templates) Tools to learn: ChatGPT + Zapier:  For custom flows from ticket to resolution Microsoft Copilot:  Deeply integrated for M365-heavy clients Tidio or Intercom:  Plug-and-play AI bots for your website Don’t try to replace your techs — empower them. AI is your new Tier 0. Need help? No worries, ThreatMate can help you on your AI journey.