While organizations invest heavily in stopping threats from entering their networks, a critical vulnerability often goes underprotected: sensitive data leaving the organization through email.
Every day, employees send thousands of emails containing confidential information – patient records, financial data, legal documents, and personally identifiable information (PII). And every day, some of those emails go to the wrong recipient.
For organizations, misdirected emails represent more than just embarrassing mistakes. They’re compliance violations, regulatory breaches and reputational disasters waiting to happen. In highly regulated industries like healthcare, financial services, legal and insurance, a single misdirected email can trigger investigations, fines, lawsuits and loss of customer trust.
The Growing Risk of Misdirected Emails
Email remains the primary channel for business communication and sensitive data transmission. The problem? Human error remains one of the leading causes of data breaches. especially via email.
According to our report, ‘The State of Human Risk 2025: The New Paradigm of Securing People in the AI Era’, email is the primary risk channel when it comes to employees making genuine mistakes (without involvement by cybercriminals). Half (49%) of cybersecurity leaders said they experienced incidents caused by misdirected email.
Regulatory enforcement is intensifying. Privacy regulations like HIPAA, GDPR, GLBA, and state-specific laws impose strict requirements for protecting sensitive data, with escalating penalties for breaches, including those caused by misdirected emails.
Misdirected emails are common and costly. Autocomplete errors, typos in email addresses, wrong attachments, and simple human oversight create daily exposure risks. When emails contain protected health information (PHI), PII or confidential business data, the consequences can be severe.
Insider threats are rising. Disgruntled employees, departing staff taking proprietary information or malicious insiders exfiltrating data through email pose significant risks that traditional security controls often miss.
The compliance landscape is expanding. New regulations and expanded definitions of protected data mean more information now falls under regulatory protection, requiring organizations to demonstrate they’re actively preventing unauthorized data disclosure.
What’s at Stake?
When sensitive data leaves your organization through a misdirected email, the impacts cascade quickly: regulatory penalties, legal liability, mandatory breach notifications, loss of competitive advantage, damage to professional relationships, and operational disruption from incident response.
For healthcare organizations, a misdirected email containing patient records triggers HIPAA breach notification requirements. For law firms, accidentally disclosing privileged client information can result in malpractice claims. For financial institutions, exposure of customer financial data violates multiple regulatory frameworks and erodes fundamental trust.
Smart DLP Powered by Behavioral AI
KnowBe4 Prevent™ reduces data breach risk by analyzing each user’s communication patterns and applying intelligent DLP to intercept threats like misdirected emails (wrong recipients or attachments), accidental exposure of sensitive data, and unauthorized data sharing or exfiltration.
Prevent combines your organization’s email policies with advanced behavioral AI that learns how each employee normally communicates. When something doesn’t look right (like a mistyped address or unusual file content), Prevent flags the risk immediately.
Intelligent protection includes:
- Misdirected email prevention: Detects autocomplete errors, typos, first-time external recipients, and greeting-recipient mismatches
- Data exfiltration protection: Flags suspicious attachments and unusual patterns from malicious insiders or compromised accounts
- Domain protection: Alerts on newly registered domains, blocks threat intelligence-listed domains, and flags impersonation attempts
- Custom DLP rules: Warns users when sending content matching company-specific sensitive keywords or patterns
- Ethical walls: Prevent Enterprise restricts information flow across departmental boundaries to maintain compliance
Real-Time Guidance Without Disruption
Prevent only prompts when a mistake or breach is about to occur, providing real-time alerts via side panel display and point-of-risk nudges with suggested fixes, without overwhelming users.
Operational Efficiency
Prevent reduces alert fatigue with self-learning behavioral analytics. Security teams gain detailed analytics and in-depth reporting to identify risky users and spot compliance issues. As one Director of Information Security noted: “It gives me that one pane of glass where I can see what data is being sent to where and if prompts are being ignored.”
Easy Microsoft 365 Deployment
Prevent deploys easily with native integration via Outlook Web Add-in and API, with full mobile and OWA support. Prevent Enterprise integrates tightly with Microsoft Azure Information Protection for enhanced content analysis.
Training and Technology Together
Technology alone won’t eliminate data loss risk. Combining KnowBe4 Prevent with KnowBe4’s Human Risk Management platform addresses data protection from both angles: technical controls using behavioral AI to stop dangerous outbound emails, and security awareness training that helps employees recognize what data requires protection and adopt secure email practices.
Complete Email Security
Modern email security requires addressing both inbound and outbound risks. KnowBe4 Defend stops sophisticated phishing and BEC attacks from reaching users. KnowBe4 Prevent stops sensitive data from leaving your organization through misdirected or malicious emails.
Together, they provide comprehensive protection that addresses the full threat landscape – reducing risk without the complexity of managing multiple disconnected solutions. Because the best time to stop a data breach is before it happens.
Learn more about how KnowBe4 Prevent can protect your organization’s sensitive data: www.knowbe4.com/products/prevent
