Network Penetration Testing for Financial Services in Chicago (IL)

 

At OCD Tech, we provide customized network penetration testing for banks, credit unions, asset managers, trading firms, payment processors, and insurance companies across the Chicago metro area. Our goal is simple: find the security gaps in your environment before an attacker—or a regulator—does.

We help Chicago financial institutions protect high-value data such as customer PII, payment card data, trading systems, loan files, and wealth management records, while supporting compliance with PCI-DSS, GLBA, NYDFS-inspired cybersecurity expectations, HIPAA (for health-related financial products), and federal guidance from the FFIEC.

 

What Is a Penetration Test?

 

A penetration test (pentest) is a controlled, ethical hacking exercise where our specialists simulate real-world cyberattacks against your network, applications, and users. The purpose is to identify, exploit, and document vulnerabilities—the same ones a criminal attacker would look for.

For Chicago financial services organizations, penetration testing helps answer practical questions:

• Can an external attacker break into our network from the internet?
• What could a compromised employee laptop or vendor account realistically access?
• Are our trading, online banking, loan origination, or payment systems exposed?
• Would our controls satisfy auditors, examiners, and insurers after an incident?

This proactive approach allows you to strengthen your defenses, reduce breach risk, and demonstrate due diligence to boards, regulators, and customers.

 

Why Penetration Testing Matters for Chicago Financial Institutions

 

Chicago is a major financial hub, home to trading exchanges, regional banks, fintechs, and insurance carriers. That makes local firms high-value targets for cybercrime, fraud, and ransomware gangs. The combination of large transaction volumes, sensitive financial records, and strict regulatory oversight means that a single breach can quickly turn into an IT, legal, and reputational crisis.

Financial institutions in Illinois must navigate complex regulatory and contractual requirements, including:

• PCI-DSS for payment card data
• GLBA Safeguards Rule for customer information
• FFIEC / OCC / FDIC / Federal Reserve guidance and examinations
• HIPAA for financial products tied to healthcare data
• Vendor and third-party risk expectations from partners and payment processors

Regular network penetration testing supports these obligations by providing evidence-based security assessments, not just paperwork and policy reviews.

We also address insider threat and assumed compromise scenarios. Employees, contractors, managed service providers, and other third parties can unintentionally—or deliberately—introduce risk. Our tests show what happens if an internal account, workstation, or vendor VPN is taken over.

 

Network Penetration Testing Services for Chicago Financial Services

 

OCD Tech offers a focused suite of IT security assessment and penetration testing services tailored to financial services environments in Chicago:

• External Network Penetration Testing
  We simulate internet-based attacks against your firewalls, VPN gateways, remote access portals, online banking, trading interfaces, and public APIs. The objective is to determine whether an attacker can gain an initial foothold or access sensitive data from outside your network.

• Internal Network Penetration Testing
  Assuming a compromise of a workstation or user account, we test how far an attacker could move within your internal environment—such as core banking systems, data centers, file shares, Active Directory, and backup infrastructure. This helps quantify lateral movement risk and identify weak segmentation and misconfigurations.

• Wireless Penetration Testing
  We assess the security of your corporate Wi‑Fi, guest networks, and branch office wireless to prevent unauthorized access from public areas, parking lots, and nearby offices. This is especially relevant for branches, trading floors, and shared office spaces in downtown Chicago.

• Web Application Penetration Testing
  We perform in-depth testing of online banking platforms, client portals, trading and brokerage applications, loan origination systems, and internal web tools. This includes identifying issues like SQL injection, cross-site scripting, authentication and session flaws, access control weaknesses, and business logic vulnerabilities.

• Social Engineering and Phishing Exercises
  We simulate targeted phishing, vishing (voice phishing), and other social engineering attacks against your employees and, where appropriate, branch staff. This evaluates security awareness, incident reporting, and Blue Team / SOC response in realistic scenarios.

Each engagement can be scoped as a traditional pentest, a more adversarial Red Team exercise, or a collaborative Purple Team engagement where we work directly with your Blue Team to improve detection and response.

 

Protect Sensitive Financial Data and Maintain Client Trust

 

OCD Tech has extensive experience working with Chicago-based financial organizations—from community banks and credit unions in the suburbs, to trading, investment, and fintech firms in the Loop. We understand the practical constraints of uptime, trading hours, customer impact, and regulatory scrutiny.

Our deliverables are designed for both technical and non-technical stakeholders:

• Clear, prioritized findings with business impact explained in plain language
• Actionable remediation steps aligned to your technology stack and risk appetite
• Evidence that supports discussions with boards, auditors, examiners, and cyber insurers

The outcome: reduced breach likelihood, faster incident response, and stronger customer confidence in how you protect their financial data.

 

Our Network Penetration Testing Process

 

We follow a structured, repeatable methodology adapted to the financial services threat landscape and your specific Chicago footprint:

• Reconnaissance
  We gather information about your public-facing and internal environment using open-source intelligence, network and application scanning, DNS and certificate analysis, and configuration review. This reveals potential attack paths without disrupting operations.

• Vulnerability Identification
  Using a combination of automated tools and manual analysis, we identify unpatched systems, weak configurations, exposed services, and architectural weaknesses in your network, servers, workstations, and applications.

• Exploitation and Lateral Movement
  We safely attempt to exploit identified weaknesses, under strict rules of engagement, to understand how an attacker could gain access, escalate privileges, move laterally, and reach critical financial systems or data. This may include assumed compromise scenarios for high-risk assets or user accounts.

• Reporting and Executive Briefing
  You receive a comprehensive yet clear report detailing each vulnerability, proof of concept where appropriate, and its potential impact on operations, customers, and compliance. We provide a prioritized remediation plan and, if requested, an executive-level summary suitable for leadership and regulators.

Our process is tailored to each client, accounting for the unique mix of on-premises infrastructure, cloud services (e.g., AWS, Azure, GCP), and third-party providers common in Chicago’s financial ecosystem.

 

Stay Compliant and Avoid Costly Fines

 

Penetration testing delivers tangible value beyond “checking a box.” For Chicago financial institutions, it helps to:

• Identify Vulnerabilities Before Attackers Do
  We uncover hidden weaknesses in your network, applications, and configurations so your teams can remediate them before they result in data breaches, wire fraud, or ransomware incidents.

• Improve Security Controls and Architecture
  By simulating realistic attacks, we test how well your firewalls, endpoint protection, MFA, SIEM, and monitoring actually perform. This supports practical improvements to your overall IT security posture.

• Support Compliance Obligations
  Regular penetration testing aligns with the expectations of PCI-DSS, GLBA, FFIEC guidance, HIPAA, GDPR (where applicable), and internal risk policies. Well-documented tests help you demonstrate due care and reduce the likelihood—and impact—of fines, consent orders, and regulatory findings after an incident.

• Reduce Downtime and Breach Costs
  Detecting and fixing weaknesses early is significantly cheaper than recovering from a successful attack that disrupts online banking, trading systems, branch operations, or payment processing. Stronger defenses mean less downtime, fewer customer issues, and lower incident response costs.

• Strengthen Incident Response Capability
  A pentest gives your SOC, Blue Team, and IT operations a chance to practice in real conditions. We can coordinate tests so your teams can observe alerts, refine playbooks, and improve detection and response times.

• Increase Customer and Stakeholder Confidence
  Demonstrating that your institution invests in independent security assessments and ethical hacking reinforces trust with clients, partners, investors, and regulators.

 

Trusted by Chicago Financial Services Organizations

 

If you operate in the Chicago financial sector and want a realistic view of your cyber risk, we can help. Our team delivers tailored penetration testing services that respect your uptime requirements and regulatory constraints while providing an unfiltered assessment of your defenses.

Contact our Chicago-focused team to discuss scope, timing, and objectives for a network penetration test aligned to your environment. We offer initial consultations to help you determine the right mix of external, internal, web, wireless, and social engineering testing for your institution.

 

Penetration Testing FAQs for Financial Services

 

How often should our financial institution conduct penetration tests?

Most regulators and industry best practices recommend at least annual penetration testing, with additional tests after major changes to your network, core banking systems, online platforms, or mergers and acquisitions. Higher-risk environments—such as trading firms and payment processors—often test more frequently.

What’s the difference between a penetration test and a vulnerability assessment?

A vulnerability assessment identifies and lists potential weaknesses but does not exploit them. A penetration test goes further by safely exploiting vulnerabilities to show what an attacker could actually do—how far they could get and what data or systems they could access. Examiners and cyber insurers generally place more weight on penetration tests.

How long does the penetration testing process take?

For most Chicago financial institutions, a focused pentest typically takes one to two weeks of active testing, plus time for planning and reporting. Larger, more complex environments—multiple data centers, cloud footprints, or numerous applications—may require longer, phased engagements.

Will penetration testing disrupt our daily operations or trading activities?

We design and schedule tests to minimize operational impact. Critical activities such as trading hours, payment cycles, and end-of-month processing are taken into account. Testing can be performed during off-peak windows, with strict change control and rollback plans, so you gain visibility into risk without unnecessary disruption.