Network Penetration Testing Services for MSPs in Chicago, IL

 

At OCD Tech, we provide specialized network penetration testing for IT Managed Services Providers (MSPs) in the Chicago area. We help MSPs protect their own environments and the client networks they manage across sectors such as finance, healthcare, manufacturing, logistics, and local government. Our work supports compliance with HIPAA, PCI-DSS, GDPR, and Illinois-specific privacy and breach notification requirements, while aligning with your existing managed security and monitoring services.

 

What Is a Penetration Test for an MSP?

 

A penetration test (pen test) is a controlled, ethical hacking exercise where we simulate real-world cyberattacks against your infrastructure and, where in scope, representative client environments. The goal is to identify and safely exploit weaknesses in your network, configurations, applications, and access controls before an attacker does.

For Chicago-based MSPs, penetration testing answers simple questions in a very direct way:

• Can someone break into your MSP network or tools and pivot into client environments?
• What damage could they do if they gained access to your RMM, PSA, backup, or remote access platforms?
• Are your security controls, monitoring, and incident response actually working in practice?

This proactive security assessment helps prevent breaches, demonstrate due diligence to your clients, and support compliance with standards such as HIPAA and PCI-DSS that are common across Chicagoland industries.

 

Why Penetration Testing Is Critical for Chicago MSPs

 

In Chicago’s dense business ecosystem, MSPs are high‑value targets. A single successful compromise of an MSP can give an attacker access to dozens or hundreds of downstream client networks. Attackers understand that your RMM tools, remote access gateways, and privileged accounts are powerful force multipliers.

Chicago MSPs typically serve clients that must comply with HIPAA (healthcare across the Loop and medical corridors), PCI-DSS (retail, financial services, payments), manufacturing regulations, and public-sector requirements. These organizations increasingly require their MSPs to show independent security testing as part of contracts, RFPs, and vendor due diligence.

Threats do not only come from the outside. Insider threats and assumed compromise scenarios matter for MSPs:

• Employees or contractors with broad access can unintentionally introduce vulnerabilities or misconfigurations.
• Compromised admin accounts or stolen VPN credentials can allow attackers to move from your environment into multiple client networks.
• Third‑party tools used for backups, ticketing, or remote support can become entry points if not properly secured.

Regular penetration testing helps validate your security posture as a service provider, harden your internal and client‑facing infrastructure, and support your positioning as a trusted, security‑minded MSP in the Chicago market.

 

Network Penetration Testing Services Tailored to Chicago MSPs

 

OCD Tech delivers a broad set of penetration testing and security assessment services designed specifically for MSPs operating in Chicago and the greater Illinois region:

• External Network Penetration Testing
  We test your internet‑facing assets—firewalls, VPNs, RMM portals, web applications, email gateways, and cloud services. The objective is to understand how an attacker on the internet would target your MSP infrastructure and attempt to gain a foothold into your network and, by extension, your clients.
• Internal Network Penetration Testing
  We simulate an attacker who already has some level of internal access—whether via a compromised workstation, a phishing victim, or a rogue insider. We identify lateral movement paths, privilege escalation opportunities, Active Directory weaknesses, and weak network segmentation between your internal systems and client environments.
• Wireless Penetration Testing
  We assess your Wi‑Fi security across main offices, branch locations, and data centers. This includes misconfigurations, weak encryption, guest/corporate network separation, and risks from rogue access points—common issues in multi‑tenant office buildings around downtown Chicago and the suburbs.
• Web Application & Portal Penetration Testing
  We test MSP‑specific web applications such as client portals, ticketing systems, custom dashboards, and integration APIs. We look for vulnerabilities including SQL Injection, Cross‑Site Scripting (XSS), authentication and session flaws, authorization bypasses, and insecure direct object references that could expose client data.
• Social Engineering & Phishing Assessments
  We run targeted social engineering campaigns against your staff—especially help desk, NOC, and engineering teams—to measure susceptibility to phishing, credential harvesting, and voice‑based attacks. This helps gauge real‑world risk and refine your security awareness training and Blue Team processes.
• Configuration Review (Config Review)
  We perform detailed configuration reviews of firewalls, RMM tools, VPNs, backup systems, and identity platforms. This complements hands‑on penetration testing by identifying systemic weaknesses such as overly permissive rules, missing MFA, weak logging, and poor role design.

 

Protect Client Data, Contracts, and Your Reputation

 

OCD Tech has extensive experience working with MSPs and IT service providers in the Chicago metro area—from small teams servicing local professional firms to larger providers supporting multi‑site healthcare and manufacturing organizations across Illinois and neighboring states.

We understand the pressures MSPs face: 24x7 uptime commitments, SLAs, vendor audits, cyber insurance requirements, and client board‑level scrutiny after every major breach in the news. Our penetration tests are built to slot into that reality, not disrupt it. The result is clear, prioritized, and business‑focused reporting you can use with technical staff, management, and client stakeholders.

 

Our Network Penetration Testing Process for MSPs

 

Our methodology is structured, repeatable, and tailored to multi‑tenant, service‑provider environments:

• Scoping & Rules of Engagement
  We work with your technical and leadership teams to define in‑scope networks, tools, and client segments, clarify any legal or contractual constraints, and agree on testing windows that minimize disruption to your operations and client services.
• Reconnaissance
  We gather information about your MSP footprint using open‑source intelligence (OSINT), network enumeration, and public data. This includes domains, exposed services, cloud assets, leaked credentials, and references to your organization and tooling on the internet.
• Vulnerability Identification
  We combine automated scanning with manual analysis to identify unpatched systems, insecure services, weak authentication, misconfigurations, and architectural weaknesses across your core infrastructure and any agreed‑upon client‑facing components.
• Exploitation & Lateral Movement
  Where allowed by scope, we safely attempt to exploit identified weaknesses to demonstrate real‑world impact: gaining elevated access, pivoting between network segments, reaching critical assets (such as RMM consoles, domain controllers, backup repositories), and simulating attacker behavior under assumed compromise conditions.
• Detection & Response Evaluation
  We observe what your Blue Team and monitoring tools detect, how alerts are generated, and how quickly incidents are handled. When requested, we can support Purple Team exercises that coordinate offensive and defensive teams to improve detection and response playbooks.
• Reporting & Remediation Guidance
  You receive a clear, structured report detailing each finding, its risk level, affected assets, attack path, and practical remediation steps. We prioritize items that could lead to widespread client impact, ransomware events, or data exfiltration, and we remain available to review fixes and retest as needed.

This process is customized for each Chicago MSP, considering your industry mix, regulatory exposure, and hosting model (on‑premise, colocation, private cloud, or public cloud providers such as AWS, Azure, and Google Cloud).

 

Compliance, Cyber Insurance, and Avoiding Fines

 

For MSPs supporting regulated clients across Illinois, penetration testing is more than a best practice—it is increasingly a contractual and regulatory expectation. Our testing services help you:

• Identify and Prioritize Vulnerabilities
  We uncover weaknesses in your systems, applications, and networks before threat actors can exploit them. This enables your team to address the most critical risks first, reducing the likelihood of a high‑impact incident.
• Improve IT Security Controls
  By simulating realistic attacks, we show how effective your existing security stack is—firewalls, EDR, SIEM, MFA, backup protections, and access controls. You gain evidence to refine policies, strengthen configurations, and justify security investments to leadership and clients.
• Support Regulatory Compliance
  Many of your clients must meet frameworks such as PCI-DSS, HIPAA, GDPR, and various state-level privacy and security laws. Demonstrable penetration testing helps you and your clients satisfy audit requirements, vendor risk assessments, and cyber insurance conditions, reducing the risk of penalties and legal exposure.
• Reduce Downtime and Breach Impact
  Addressing issues before they are exploited significantly lowers the probability of ransomware, business interruption, and data loss. This protects your recurring revenue, prevents SLA violations, and helps you avoid expensive cleanup and reputational damage after an incident.
• Strengthen Incident Response
  Our testing provides a safe way to exercise your incident response runbooks—from initial alert through containment, eradication, and recovery. Your team learns what actually works under pressure and where processes need tightening.
• Increase Client Confidence and Win Business
  Regular, independent security assessments send a clear message: your MSP takes security seriously. This can be a decisive advantage in competitive RFPs, renewals, and board‑level due diligence for Chicago‑based organizations looking for a long‑term security‑focused IT partner.

 

Trusted by Chicago MSPs to Keep Their Networks and Clients Secure

 

If you manage IT for multiple organizations, you are effectively part of their security supply chain. One weak link can affect an entire portfolio of clients. Our Chicago‑focused penetration testing services help you close that gap.

To discuss a network penetration test tailored to your MSP environment, contact our Chicago team. We will help you define scope, align with your operational needs, and build a testing plan that fits your regulatory and client obligations.

 

Penetration Testing FAQs for Chicago MSPs

 

How often should an MSP conduct penetration tests?
Most MSPs benefit from at least one comprehensive penetration test per year, plus additional tests after major changes—such as new data centers, significant onboarding of high‑risk clients, deployment of new RMM platforms, or material changes to your network architecture.

What’s the difference between penetration testing and vulnerability assessments?
A vulnerability assessment identifies and reports potential weaknesses but does not attempt to exploit them. A penetration test goes further by safely exploiting vulnerabilities to show how an attacker could chain them together, what they could access, and the real risk to your MSP and its clients.

How long does the penetration testing process take?
For a typical MSP environment, active testing usually takes one to two weeks, depending on scope and complexity. Larger, multi‑site or hybrid‑cloud environments may require additional time for thorough coverage and coordination.

Will penetration testing disrupt our MSP operations or client services?
We plan testing to minimize operational impact. Most activities can be performed with little to no visible disruption, and higher‑risk steps are scheduled during agreed maintenance or off‑peak windows. All work is coordinated with your team so client service levels remain intact.