Working PI
by Isaac Peck, Senior Broker at OREP.org
You log in, expecting to finalize a report and send it off to one of your larger clients, only to find your system locked, case files gone, and a message blinking on the screen:
“YOUR FILES ARE ENCRYPTED. To regain access, you must pay a ransom. Do not attempt to decrypt or modify the files yourself. Any unauthorized action will result in permanent data loss. Payment instructions are below. You have 72 hours.”
Directly below the words, a clock begins counting down.
You feel panic setting in. To make matters worse, you had committed to delivering a rush investigation report to your client this morning in a time-sensitive litigation case. You can’t access reports, contact clients, or meet deadlines. You’re losing money, time, and worst of all, your clients’ trust.
You thought your investigation business was too small to be a target. But here you are.
In fact, small business owners like me (and you) frequently think: “My business is too small for me to have to worry about cyberattacks.”
This type of mentality only compounds the problem. According to recent national data, more than half of U.S. cyberattacks now target small businesses, not large corporations. Firms with fewer than 100 employees are significantly more likely to be targeted than larger companies, largely because they lack dedicated IT staff, formal security protocols, and incident-response plans. In other words, they’re easier targets.
The financial fallout doesn’t have to be catastrophic to be devastating. Industry reports estimate that even modest cyber incidents routinely cost small businesses tens of thousands of dollars once downtime, data recovery, legal obligations, and lost business are factored in. For a solo investigator or small PI firm, that kind of disruption can halt operations entirely.
And unlike large companies, investigators usually don’t have layers of redundancy. One compromised laptop, one hijacked email account, or one ransomware event can shut down your ability to deliver reports, communicate with clients, or access case files—right in the middle of pressing deadlines. The reputational hit an investigator takes when they tell their clients they can’t assist on a case because they’ve been hacked can be heavy.
Cyber Threats Grow
Many small business owners—including PIs—assume cyberattacks are a problem for big companies with big budgets. That assumption is increasingly wrong.
In 2025, more than 60 percent of U.S. small businesses reported a cyberattack, and firms with under 100 employees were 2.5 times as likely to be targeted as companies with 500 or more staff.
Why the shift? Cybercriminals have now learned that small businesses are often easier targets. Large organizations may offer larger payouts, but they also invest heavily in cybersecurity infrastructure, monitoring, and response teams.
Small firms rarely have those layers of defense. With automated tools, ransomware-as-a-service kits, and AI-generated phishing campaigns, attackers can efficiently target thousands of smaller businesses at once, knowing that even modest ransom payments add up quickly.
The financial consequences are not theoretical. According to Verizon’s 2024 Data Breach Investigations Report, small business data breaches can cost anywhere from $120,000 to over $1.2 million, depending on the severity. Other industry studies released last summer put the average cost of a single cyber incident at roughly $25,000—far more than most investigation businesses can absorb without serious disruption.
And cost is only part of the damage. Ransomware attacks now dominate the small-business threat landscape, often using double-extortion tactics: encrypting files while simultaneously threatening to release sensitive client data. Phishing emails have become more convincing, mimicking attorneys, insurance adjusters, and corporate clients that investigators work with every day. In some cases, attackers even use deepfake audio or video to impersonate trusted contacts.
Software tools, mobile technology, cloud storage, and third-party platforms have expanded the attack surface even further. Each login, shared file, or connected vendor introduces another potential point of entry. For businesses without IT monitoring or incident-response plans, attacks can go undetected until systems are locked—or client data has already been compromised.
This isn’t a call to panic. It is a call to acknowledge reality. Cyberattacks today are aggressive, targeted, and financially motivated. Even when a business survives the initial hit, the operational disruption and reputational damage can linger long after systems are restored.
That’s because economic damage isn’t the only kind of damage you’re going to worry about when running your firm. Compromised databases, stolen client data, and prolonged communication interruptions all disrupt operations, expose you to legal and financial fallout, and worst of all, directly threaten your trusting relationship with your clients.
As one cybersecurity expert put it: it only takes one successful attack. The question isn’t whether investigators are too small to be targeted—it’s whether they’re prepared when it happens.
Unique Risks for Investigators
Private investigators face unique cyber risks that make them especially vulnerable to digital attacks. Unlike larger firms with dedicated IT teams, most investigators operate as solo practitioners or small businesses.
Nevertheless, even the smallest investigation offices handle highly sensitive data every day: case details, witness information, surveillance footage, background check results, confidential details, and access credentials all flow through their systems, often via unsecured emails or cloud-based platforms.
Cybercriminals know that investigators are deeply embedded in legal cases, insurance claims, and corporate investigations, often under tight deadlines and with limited tech support. A well-timed phishing email or ransomware attack can severely compromise ongoing cases, damage attorney relationships, jeopardize evidence chains, and quickly spread malware to the investigator’s email contacts.
Private investigators rely heavily on mobile devices, remote access, and third-party software to stay efficient and responsive. Each of these tools introduces vulnerabilities. Tablets and smartphones used in the field lack robust endpoint protection, making them easy targets for malware or unauthorized access. A single compromised login (especially one reused across platforms) can expose sensitive client files, investigation reports, surveillance video, and even financial data.
Third-party software adds another layer of risk. That vendor platform you rely on for case management, background searches, or database access is a target. If one of your vendors suffers a breach, you could be held responsible for any client data exposed, particularly under strict privacy laws or attorney-client privilege requirements.
Email remains a major threat vector. Investigators routinely communicate with attorneys, insurance adjusters, clients, witnesses, and law enforcement, often exchanging documents and links. A hacked email account can be used to send malware to dozens of contacts, triggering reputational damage, regulatory scrutiny, and potential lawsuits.
What’s even scarier is that because private investigators often work solo or in small teams, cyberattacks may go undetected until serious damage has already occurred. You probably haven’t scaled up to the point of having a dedicated IT team. That means malware can spread, or additional data can be stolen before an issue is even discovered.
Unlike other professions, PIs rarely have the luxury of pausing operations to investigate a breach. Every day you’re closed means missed deadlines, frustrated clients, and loss of potential business.
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The Role of Insurance
When a cyber incident hits, speed matters. For investigators, the real damage often isn’t just the ransom demand or the technical cleanup—it’s the downtime, the missed deadlines, and the loss of client confidence that follows. Cyber insurance exists to help businesses recover quickly and responsibly. For PIs that means having access to technical experts who can investigate what happened, contain the breach, and restore systems so work can resume. It also means guidance on how to communicate with attorneys, clients, and other parties if sensitive information is compromised.
Notification Costs: If your case files or client data are compromised, you may be legally required to notify affected parties. OREP’s cyber policy covers the cost of sending notification letters or emails, setting up a call center, and offering credit or identity monitoring. These steps help preserve client trust and meet compliance obligations.
Crisis Management Costs: A cyberattack can damage your reputation with law firms, insurance companies, corporate clients, and individuals overnight. This coverage helps you respond strategically, from hiring PR professionals and obtaining legal guidance to managing communications with clients, regulators, and industry partners.
Forensic Investigation Costs: After a breach, you’ll need to understand how it happened and what was affected. OREP’s policy pays for cybersecurity experts to investigate the incident, assess your systems, and identify vulnerabilities.
Extortion Costs: Ransomware attacks are on the rise, and investigators are not immune. If cybercriminals lock your files and demand payment, OREP’s policy includes support for negotiators, approved ransom payments, and technical assistance to help restore access and minimize downtime.
Technology Fraud and Theft Losses: Investigators are frequently targeted by phishing scams and fraudulent payment schemes. This coverage protects against financial losses from fake wire transfers, spoofed emails, and other forms of digital deception that can drain your business accounts.
Third-Party Liability: If your email or case management software is compromised and spreads malware to clients or industry contacts, you could be held liable. OREP’s policy includes third-party coverage to help manage legal exposure and repair professional relationships.
OREP’s starter cyber policy is only $125 per year and includes up to $100,000 for cyber and technology security incidents, along with coverage for privacy fines or penalties that can arise even when the investigator is the victim of an attack.
It also addresses the real-world costs that follow a breach, including notification expenses, crisis management, forensic investigation, ransomware extortion, and technology fraud losses. (Sublimits apply. Higher limits are available for additional premium.)
For You, For Your Clients
Cyber risk is no longer a theoretical problem reserved for large corporations or tech companies. It’s an operational reality for investigators who rely on email, cloud storage, mobile devices, and third-party platforms to do their work.
Whether a firm is large or small, client data is still client data—and protecting it is an essential part of maintaining professional standards.
Cyber insurance doesn’t replace good practices or sound judgment, just as E&O insurance doesn’t replace competent investigative work. What it does provide is a backstop when prevention fails. When systems go down, data is compromised, or communication with clients is disrupted, the ability to respond quickly and professionally matters. In those moments, the question isn’t whether a breach should have happened—it’s how well the investigator is prepared to deal with it.
Private investigators spend their careers helping their clients manage risk—protecting their own businesses is no different. Cyber insurance is simply another tool for doing that thoughtfully, deliberately, and with an eye toward long-term stability.
About the Author
Isaac Peck is the Publisher of Working PI magazine and the President and Senior Broker of OREP.org, a leading provider of E&O insurance for the PI profession. Working PI is the most widely read print magazine for investigators nationwide, reaching over 25,000 PIs. PIs who become OREP Members enjoy two CE courses (15 hours) at no charge (Visit OREP.org/PI-Members for details). Email Isaac at isaac@orep.org or call toll-free (888) 347-5273. CA License #4116465.
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