Multistep Phishing Attacks and the Power of Personalization: A Comprehensive Q&A Guide

What is phishing?

Phishing is a type of cyberattack where criminals impersonate trusted entities to trick people into revealing sensitive information or performing actions that compromise security. This could involve sharing passwords, clicking malicious links, or transferring money (Verizon Data Breach Investigations Report, 2024).

How have phishing strategies evolved?

Phishing has evolved from simple, generic emails to sophisticated, targeted campaigns. Early phishing relied on mass emails with obvious errors, but today’s attacks are often highly convincing and tailored to specific people, roles, or organizations (Barracuda, 2025 Threat Spotlight). Attackers now use multiple stages and channels, making their tactics harder to detect and defend against.

Why are multistep and personalized phishing attacks more dangerous?

Multistep and personalized phishing attacks are more dangerous because they:

• Use several coordinated steps, increasing the chance of success.

• Leverage personal or organizational information, making messages seem legitimate.

• Bypass traditional security tools by moving across email, SMS, phone calls, and social media.

• Adapt in real time, responding to victims’ actions and feedback (Proofpoint State of the Phish, 2024).

What Is a Multistep Phishing Attack?

How do multistep phishing attacks differ from traditional phishing?

Traditional phishing typically involves a single deceptive email. In contrast, multistep phishing attacks unfold in several phases, with each step building on the previous one. Attackers may use information gathered in early interactions to customize later steps, making the attack more convincing and harder to spot (IBM X-Force Threat Intelligence Index, 2024).

Key differences:

• Traditional phishing: One-off, generic, often easily detected.

• Multistep phishing: Multi-phase, adaptive, targeted, and much harder to detect.

What are the typical stages of a multistep phishing attack?

A typical multistep phishing attack includes:

1. Initial contact and reconnaissance: The attacker sends a benign or curiosity-arousing message via email, SMS, or social media.

2. Trust-building and social engineering: The attacker impersonates a trusted entity, using details from public sources or previous breaches.

3. Technical complexity: Attackers might introduce CAPTCHAs, QR codes, or shift to another channel (like phone or chat) to evade detection.

4. Final exploitation and data theft: The attacker deploys malware, harvests credentials, or manipulates the victim into transferring funds or sensitive data (Cofense Phishing Threat Landscape, 2024).

Example:

In 2024, the University of Utah was attacked through a series of emails offering fake jobs and account verifications. Attackers then used Google Forms and fake university websites to collect credentials, followed by SMS messages to harvest additional information. This multi-channel, multi-step approach made the attack difficult to detect and stop (KSL News, 2024).

Why are multistep phishing attacks so difficult to detect?

• Use of multiple channels: Attackers switch between email, SMS, phone, and social media.

• Adaptive tactics: Each step is tailored based on the victim’s responses.

• Technical evasion: CAPTCHAs, QR codes, and legitimate-looking attachments help bypass automated detection.

• Credential harvesting: Compromised accounts are used to send phishing emails, making them appear authentic (Abnormal Security, 2024).

How Do Hackers Personalize Phishing Attacks?

What is phishing personalization and why does it matter?

Phishing personalization is when attackers use specific, contextual information about the target—like job role, department, or recent activities—to craft messages that feel authentic and relevant. Personalized phishing is more likely to succeed because it appears trustworthy and timely (Hoxhunt Phishing Benchmark Report, 2025).

How do attackers gather personal and organizational information?

Attackers use several methods:

• Social media scraping: Collecting information from LinkedIn, Facebook, Twitter, and other platforms.

• Open-source intelligence (OSINT): Mining public websites, press releases, and regulatory filings.

• Dark web data and credential leaks: Buying and selling stolen credentials and personal data (Recorded Future, 2024).

• Mimicking internal communication styles: Analyzing previous email threads or using AI to replicate tone, formatting, and signatures (Barracuda, 2025 Threat Spotlight).

Which roles, departments, or access levels are most targeted?

Attackers focus on people with valuable access or sensitive responsibilities:

• Executives (C-suite): CEOs, CFOs, CISOs.

• Privileged users: IT admins, system owners.

• Finance, HR, and IT departments: Handle payments, payroll, and system access.

• New employees and third-party vendors: Often targeted before they’re fully trained or have strong security habits (Verizon DBIR, 2024).

Example:

In 2025, healthcare billing staff were targeted with personalized “insurance verification” emails sent from compromised patient portals. These emails contained real patient and billing data, bypassing spam filters and leading to a major breach (Healthcare IT News, 2025).

What techniques make personalized phishing so convincing?

• Department-specific lures: Fake invoices for finance, benefits enrollment for HR, system upgrade alerts for IT.

• Role-based requests: Urgent access requests for IT admins, board document shares for executives.

• Use of real or recent internal documents: Attackers attach or reference documents that appear legitimate and timely.

• Impersonation of known contacts: Using names and email formats familiar to the target (Proofpoint State of the Phish, 2024).

Latest Trends and Developments

How is artificial intelligence changing phishing attacks?

AI has revolutionized phishing by:

• Automating content generation: AI tools create emails that mimic writing styles and personalize content at scale.

• Voice and video cloning: AI can clone voices of executives for convincing vishing (voice phishing) and deepfake video scams.

• Dynamic attack sequences: AI adapts attacks in real time based on victim interactions, creating a feedback loop that increases success rates (Abnormal Security, 2025 AI Phishing Trends).

Expert insight:

“In 2025, we will witness a new wave of attacks that combine both human vulnerabilities and direct assaults on security solutions. Cybercriminals have long targeted human behavior, exploiting psychological weaknesses, while also attempting to poison AI models and obfuscate malicious elements to evade detection. The frequency and depth of these combined attacks will increase to levels we've never experienced before, making this the primary focus for cybersecurity moving forward.”

— Barracuda Threat Analysts (Barracuda, 2025 Threat Spotlight)

What new evasion tactics are attackers using?

• QR code phishing (“quishing”): Attackers embed QR codes in emails or printed materials, leading victims to malicious sites mimicking login portals (Proofpoint, 2024).

• CAPTCHA and steganography: CAPTCHAs add legitimacy and block automated analysis; steganography hides malicious code within images or files (Cofense, 2024).

• Multi-channel attack coordination: Attackers start with email, then move to SMS, phone, or chat apps to complete different attack stages (Abnormal Security, 2024).

Example:

At a 2025 tech conference, attackers distributed brochures with QR codes leading to fake login pages. Employees from several Fortune 500 companies scanned the codes, resulting in the theft of thousands of credentials and $15 million in cryptocurrency losses (SC Magazine, 2025).

Statistical Data

How prevalent are multistep and personalized phishing attacks?

• 94% of organizations experienced phishing attacks in 2024 (Proofpoint State of the Phish, 2024).

• 96% suffered negative fallout, including financial loss, data breaches, and reputational harm (IBM Cost of a Data Breach Report, 2024).

• 493.2 million phishing attacks were recorded in Q3 2023—a 173% increase from the previous quarter (APWG Phishing Activity Trends Report, Q3 2023).

• 3.4 billion phishing emails are sent daily, with 1.2% containing malicious content (Verizon DBIR, 2024).

• 83% of organizations are expected to face at least one phishing attack annually in 2025 (Barracuda, 2025 Threat Spotlight).

How effective are personalized attacks compared to generic ones?

• Click-through rates: Personalized phishing emails see a 14.2% click rate vs. 2.1% for generic lures (Hoxhunt Phishing Benchmark Report, 2025).

• Bypass rates: 67% of personalized phishing emails evade secure email gateways (Barracuda, 2025 Threat Spotlight).

• Cost per incident: The average cost of a personalized phishing breach is $4.9 million, compared to $1.2 million for generic attacks (IBM Cost of a Data Breach Report, 2024).

• Median time to click: Users fall for phishing emails in less than a minute—median time to click is 21 seconds, and it takes just another 28 seconds to supply requested information (Cofense, 2024).

Defending Against These Threats

What are the best practices for preventing multistep and personalized phishing?

1. Regular, adaptive security awareness training

• Reduces failure rates from 11% to below 2% within a year (Hoxhunt Phishing Benchmark Report, 2025).

• Reporting rates double from 34% to 74% after 12 simulations.

• Adaptive training tailors simulations to department risk profiles and individual histories.

2. Role-based access controls and monitoring

• Restrict administrative privileges to only those who need them.

• Monitor access patterns for anomalies, especially among privileged users and new employees (NIST Cybersecurity Framework, 2024).

3. Multi-factor authentication (MFA) and advanced email filtering

• MFA is highly effective, especially with phishing-resistant methods like FIDO security keys or biometrics (Google Security Blog, 2023).

• Deploy AI-powered anti-phishing tools that analyze metadata, detect spoofed domains, and adapt to new attack patterns (Abnormal Security, 2025 AI Phishing Trends).

4. Incident response planning

• Develop and rehearse an incident response plan for quick action if a breach occurs.

• Encourage early reporting and maintain detailed access logs for investigation and containment (SANS Institute Incident Response Handbook, 2024).

Responding to Suspected Attacks

How should you report and respond?

If you suspect a phishing attack:

• Report suspicious messages using your organization’s reporting tools or contact IT/security immediately (NIST Cybersecurity Framework, 2024).

• Do not click links, download attachments, or reply to suspicious messages.

• Save the message and any related communications for investigation.

What steps can limit the damage?

• Isolate affected accounts: Change passwords and revoke access for compromised accounts.

• Engage incident response: Follow your organization’s response plan to contain and investigate the breach.

• Notify stakeholders: Inform management, legal, and affected parties as required by policy and regulations.

• Monitor for further activity: Watch for signs of lateral movement or additional attacks (SANS Institute Incident Response Handbook, 2024).

How Brightside AI Uses Digital Footprint Analysis to Counter Personalized Phishing

Traditional phishing training tools often rely on generic simulations or surface-level personalization—like referencing an employee’s department or job title. But modern attackers go much deeper, gathering personal, behavioral, and even psychological data to craft highly convincing, multistep phishing campaigns. Brightside AI counters this threat by flipping the model: using the same methods attackers use—but defensively.

Brightside’s core innovation lies in its AI-powered Digital Footprint Analysis, a technology that maps the publicly exposed information of every employee across the internet. Unlike most cybersecurity awareness platforms that stop at email and role-based data, Brightside dives into what attackers actually see and use—including personal social media posts, leaked credentials, data breach mentions, publicly exposed phone numbers, usernames, interests, online habits, and even location patterns.

By gathering and analyzing this data, Brightside creates a real-time threat profile for each employee—whether they’re a CISO, a marketing intern, or a third-party contractor. This personalized view allows the platform to simulate attacks that match the style and sophistication of real-world spear phishing campaigns. For example, if an employee frequently posts about hobbies like travel or gaming, or is active on niche forums, Brightside can simulate an email using those exact interests as bait—mirroring the kind of highly convincing hooks attackers would use.

Where other tools create phishing simulations from templates, Brightside builds them from actual exposed data, meaning each employee’s training is directly relevant to their real-world risks. The result is not only a more effective simulation, but also a higher level of engagement. Employees are more likely to take phishing seriously when they see how much personal information is available and how convincingly it can be used against them.

Additionally, Brightside provides employees with a personal security portal, where they can view their digital footprint, understand what’s exposed, and take recommended actions to minimize risks—like removing old accounts, changing passwords, or deleting public records. This turns security from an abstract company policy into a personal responsibility, enhancing vigilance across all departments and seniority levels.

For organizations, this approach is doubly powerful. Not only does it improve training effectiveness, but it also acts as an early warning system. Brightside’s platform flags high-risk individuals, monitors changes in exposure over time, and helps security teams prioritize resources based on actual, observed threat vectors—not just theoretical ones.

In a landscape where attackers are using AI and OSINT tools to tailor phishing campaigns with extreme precision, Brightside gives defenders a way to out-personalize the attackers—at scale, with automation, and with empathy for the user experience. It’s not just about catching clicks anymore—it’s about building a culture where every employee understands how their digital presence can be weaponized, and how they can take control of it.

Learn more how Brighside personalizes simulations in another blog article "The Personalization Revolution in Social Engineering: Why It Matters and How to Fight Back".