Email remains the primary attack vector for initial access despite decades of security improvements. Spam filters catch obvious threats whilst sophisticated attacks bypass detection through careful social engineering, legitimate infrastructure abuse, and techniques specifically designed to evade automated filtering. Organisations deploy email security gateways, implement SPF and DMARC, and train users on phishing awareness. Attackers adapt faster than defences improve, finding new ways to deliver malicious content through the communication channel organisations depend on most.
Why Email Security Still Fails
Email authentication protocols prevent domain spoofing but don’t address compromised legitimate accounts. Attackers using breached credentials send phishing emails from real accounts that pass all authentication checks. Recipients trust emails from known senders without suspecting compromise. Polymorphic phishing generates unique messages for each recipient, defeating signature-based detection. Attackers customize emails using information scraped from social media and data breaches. These targeted messages appear legitimate because they reference real information about recipients.
Expert Commentary
Name: William Fieldhouse
Title: Director of Aardwolf Security Ltd
Comments: “Email security testing consistently reveals that whilst basic phishing gets blocked, sophisticated business email compromise attempts reach inboxes regularly. Users receive convincing emails from compromised accounts requesting wire transfers, credential resets, or sensitive information. Technical controls alone can’t stop these attacks.”
Strengthening Email Security
Implement advanced threat protection that analyses email content, attachments, and links in sandboxed environments. URL rewriting and time-of-click analysis catch phishing sites that didn’t exist when emails were sent. Attachment sandboxing detonates malicious files before they reach users. Enable multi-factor authentication for all email accounts to prevent credential stuffing attacks. Compromised passwords pose less risk when attackers can’t bypass secondary authentication. This single control prevents numerous email-based attacks.
Regular web application penetration testing should include email security assessment. Professional testing attempts to bypass email filters using real attacker techniques, revealing detection gaps.
Monitor for signs of account compromise beyond failed login attempts. Unusual sending patterns, inbox rule changes, and access from new locations all indicate potential compromise requiring investigation.
Working with the best penetration testing company includes realistic email-based social engineering testing that validates user awareness and technical controls together.
User Training Beyond Generic Awareness
Train users on specific email threats they actually face rather than generic phishing examples. Business email compromise targeting finance teams requires different training than credential phishing targeting IT staff. Relevant, role-specific training proves more effective than one-size-fits-all awareness. Conduct simulated phishing that teaches rather than punishes. When users click simulated phishing links, provide immediate educational feedback explaining warning signs they missed. This approach builds practical skills through experience. Email security requires layered defences combining technical controls, user awareness, and organisational processes that together reduce risk whilst acknowledging that perfect prevention remains impossible.
