How Phishing Works

Phishing attacks have become increasingly sophisticated, leveraging human psychology and trust to deceive individuals into revealing sensitive information. Attackers impersonate trusted entities, create a sense of urgency, and personalize their messages to increase credibility. Key tactics include domain deception, where fraudulent URLs closely mimic legitimate sites, and the exploitation of compromised hosting services to deliver malicious content. Advanced techniques, such as automation and artificial intelligence, further enhance the effectiveness of phishing campaigns, allowing for mass distribution and highly targeted attacks. Once inside a network, attackers can exploit unpatched vulnerabilities to gain control, spread malware, and exfiltrate sensitive data, highlighting the critical need for robust phishing prevention and infrastructure security. By focusing on employee training and vulnerability management, organizations can better defend against both the initial phishing attempt and the potential fallout from a successful breach.
Written by
Joshua Crumbaugh
Published on
September 10, 2024

5.1 The Basics: Crafting a Convincing Phish

Phishing attacks are highly effective because they exploit human psychology and trust. Attackers craft messages that seem legitimate, often mimicking trusted sources or creating a sense of urgency to deceive individuals into giving up sensitive information. Below are the key elements of crafting a convincing phishing attempt:


  • Impersonation of Trusted Entities: Attackers pose as well-known companies, institutions, or even colleagues. They create emails that mimic official communications by using logos, language, and even domain names that closely resemble legitimate ones. This tactic lowers the victim’s guard, making them more likely to trust the message.
  • Creating a Sense of Urgency: Phishing emails often include urgent warnings like “Your account will be locked in 24 hours” or “Immediate action required to avoid a security breach.” This urgency triggers emotional responses, causing recipients to act quickly without verifying the authenticity of the message.
  • Personalization: A key to a convincing phish is personalization. Attackers use the recipient’s name, job title, or other details to make the email seem more legitimate. By tailoring the message to the individual, attackers increase the chances that the victim will engage with the content.
  • Convincing Language and Formatting: Phishing emails are often professionally written and formatted to resemble real corporate communications. Attackers avoid glaring grammatical errors and use similar fonts, logos, and branding colors to mimic legitimate companies.
  • Inserting Malicious Links or Attachments: Most phishing emails include links to fake login pages or malware-infected attachments. The links may be disguised as something harmless, such as “View your invoice” or “Update your account,” leading the victim to a malicious site or triggering a malware download.
  • Psychological Triggers: Phishing relies heavily on emotional manipulation. Fear, curiosity, and trust are common psychological triggers used to cloud judgment and prompt the victim to act impulsively. Attackers craft scenarios where recipients feel compelled to act immediately, such as account issues or unexpected rewards, without properly vetting the source.

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5.2 Domain Deception: How Attackers Choose and Use URLs

Domain deception is a core tactic used in phishing attacks, where attackers craft URLs to appear legitimate and trick users into interacting with malicious sites. This manipulation of URLs can lead to stolen credentials, financial fraud, or malware installation. Understanding how attackers manipulate domains is crucial for spotting phishing attempts. Here are the most common techniques:


  • Typosquatting: Attackers register domains that closely resemble legitimate ones, relying on users mistyping a web address. For instance, instead of “paypal.com,” a phishing link might be “paypa1.com” or “paypol.com.” A minor misspelling can go unnoticed, especially in situations where users are rushed or distracted. These slight differences allow attackers to deceive users into thinking they are visiting the correct website.
  • Subdomain Spoofing: Attackers can manipulate subdomains to make URLs appear legitimate. For example, a URL like “secure.login-paypal.com” might look like it's connected to PayPal, but the actual domain is “login-paypal.com”, which could be owned by the attacker. Users often trust subdomains like "secure" or "login," making this tactic highly effective in phishing attempts.
  • Use of Internationalized Domain Names (IDN) Homograph Attacks: Phishers exploit characters from non-English alphabets that resemble English letters. This is known as an IDN homograph attack. For instance, the Cyrillic letter "а" is visually similar to the Latin "a." A URL like “xn--pple-43d.com” could be disguised as “apple.com,” tricking users into believing they are on a legitimate site.
  • URL Shortening Services: Attackers use URL shortening services, such as bit.ly or tinyurl.com, to obscure the destination of a malicious link. Users are unable to see the full URL and might click on the shortened link without realizing it leads to a harmful site. This method adds a layer of anonymity and disguises the true intent of the URL.
  • HTTPS and SSL Deception: Many users mistakenly believe that a padlock icon or “https” in the URL means a site is completely safe. Attackers exploit this by obtaining legitimate SSL certificates for their fake domains. For example, “https://secure-update-paypal.com” may appear secure because of the SSL certificate, but it is still a fraudulent site. Users are more likely to trust these fake sites, especially when they see the padlock symbol or “https” in the browser.
  • Domain Lookalikes and Visual Deception: Attackers create visually similar domains by adding/removing characters, using hyphens, or swapping letters. Examples include “faceb0ok.com” instead of “facebook.com” or “google-secure-login.com” instead of “google.com.” This visual deception makes it easier to trick users who glance at the URL without examining it closely.

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5.3 The Role of Hosting and Infrastructure in Phishing

The infrastructure behind phishing attacks plays a critical role in the success of these scams. Attackers rely on various hosting services and servers to deliver their fraudulent messages and host malicious websites, ensuring their operations can scale and remain undetected for as long as possible. Below are the key ways hosting and infrastructure are used in phishing:


  • Compromised Servers: Attackers often hijack legitimate websites and servers to host their phishing pages. By compromising trusted infrastructure, they can make their phishing emails and links seem more legitimate, increasing the likelihood that victims will click on malicious links without suspicion.
  • Bulletproof Hosting: Certain hosting providers, known as bulletproof hosts, are notorious for allowing illegal or unethical activity on their servers. These hosts rarely take down phishing sites or spam servers, providing a safe haven for attackers to operate without fear of their sites being removed or reported.
  • Domain Spoofing and Fast-Flux Hosting: Attackers use fast-flux hosting techniques to rapidly switch the IP addresses associated with a domain. This makes it harder for authorities to track and shut down phishing websites. Additionally, domain spoofing tricks users into thinking they’re interacting with legitimate websites by using URLs that closely resemble real domains.
  • Malware Distribution via Hosting: Phishers often use hosting services to store and distribute malware. Once a victim clicks on a phishing link, they may unknowingly download malware hosted on these servers. The malware could include ransomware, keyloggers, or other types of malicious software designed to steal sensitive information.
  • Phishing Kits and Infrastructure-as-a-Service: Many phishing attacks are supported by pre-made phishing kits that attackers can easily deploy. These kits contain all the necessary code, templates, and infrastructure needed to execute phishing campaigns, allowing less technical attackers to run sophisticated attacks with minimal effort.
  • Cloud Services Exploitation: Attackers increasingly exploit cloud services like Google Drive or Dropbox to host phishing content. Since these platforms are trusted by users, phishing links hosted on them are less likely to raise suspicion. Additionally, using cloud-based services allows phishers to bypass traditional security filters.

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5.4 Advanced Techniques: Automation and AI in Phishing

As phishing attacks have evolved, attackers have increasingly turned to advanced technologies such as automation and artificial intelligence (AI) to enhance their campaigns. These techniques allow phishers to scale their operations, target victims more effectively, and evade detection. Below are the advanced methods by which automation and AI are being used in phishing:


  • Automated Phishing Campaigns: Automation enables attackers to send thousands of phishing emails at once, targeting a wide range of individuals. These campaigns are often pre-programmed, allowing attackers to mass-distribute phishing messages without requiring manual effort for each email. Automation can also trigger follow-up emails, making the campaign seem more credible.
  • AI-Powered Email Personalization: AI algorithms can analyze publicly available information, such as social media profiles or professional networking sites, to craft highly personalized phishing emails. By using data to tailor each message to the recipient's specific interests or background, AI increases the likelihood that the target will trust the email and take the desired action.
  • Phishing Chatbots: Attackers use AI-powered chatbots to engage with victims in real-time, mimicking customer service agents or technical support representatives. These chatbots can guide victims through phishing scenarios, prompting them to disclose sensitive information or download malicious files without realizing they are interacting with an attacker.
  • Spear Phishing and AI-Assisted Targeting: AI is also used to refine spear phishing techniques, enabling attackers to target high-value individuals with precision. AI can help identify key individuals within an organization and gather relevant data about them to make the phishing message highly believable and relevant to their role, increasing the chances of success.
  • Natural Language Processing (NLP) for Crafting Messages: AI tools that use natural language processing are employed to generate phishing emails that are linguistically accurate and free of the telltale grammatical errors that typically raise suspicion. This makes the phishing email appear more professional, increasing the likelihood of a successful attack.
  • AI for Evasion Tactics: Phishers leverage AI to adapt and evade detection by anti-phishing tools and email filters. Machine learning algorithms can modify phishing messages to bypass filters by slightly altering content, keywords, or structures in a way that avoids triggering security systems while still being convincing to human recipients.

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5.5 How Your Vulnerabilities Become The Hacker’s Tools

Phishing isn’t just about stealing credentials; it’s often the gateway to something much worse. Hackers use phishing as their entry point, and once they’re inside, they rely on your unpatched and vulnerable systems to move freely through your network. It’s not a matter of if they’ll get in—it’s when. When those hackers gain access, will they be limited to a single system, or will they spread like wildfire, infecting every device and locking down your network with ransomware? This is why focusing on phishing prevention and securing your infrastructure against vulnerabilities are both critically important. Here’s how attackers turn phishing and unpatched software into their most powerful tools:


  • Initial Entry via Phishing: Phishing is often the first step, where attackers trick employees into clicking malicious links or downloading infected attachments. This gives hackers access to credentials or a foothold on a single device, allowing them to execute more advanced attacks.
  • Exploiting Unpatched Vulnerabilities: Once inside, hackers target any outdated software or unpatched systems. These vulnerabilities allow them to escalate privileges and move laterally within the network. What started as a phishing attack on one person can quickly turn into full-scale infiltration of your entire infrastructure.
  • Network-Wide Ransomware Deployment: Unpatched systems are perfect for attackers looking to deploy ransomware. After gaining access via phishing, they spread the ransomware across all vulnerable systems, locking you out of critical data and demanding large sums to regain access. Without proper defenses, this can shut down operations completely.
  • Privilege Escalation for Full Control: Phishing opens the door, but unpatched software gives hackers full control. By exploiting known vulnerabilities, they can gain administrative privileges, disabling security measures, and taking full control of systems. This allows them to steal data, deploy malware, and even cover their tracks.
  • Spreading Through the Network: With phishing as the entry point and unpatched software as the key, attackers can spread malware to every connected system. They use lateral movement techniques to infect other machines, servers, and even partner networks, making the damage widespread and harder to contain.
  • Data Theft and Exfiltration: Phishing gives hackers a foothold, but it’s your vulnerable software that allows them to steal valuable data. They use these vulnerabilities to extract sensitive information like customer records, financial data, or intellectual property, selling it on the dark web or using it for further attacks.
  • Persistent Access with Backdoors: After gaining access via phishing and exploiting vulnerabilities, attackers often install backdoors that give them long-term access to your network. Even if the initial breach is detected and addressed, they can re-enter at any time, continuing to steal data or deploy malware.
  • Preventing Both Entry and Spread: At PhishFirewall, we focus on both keeping attackers out through phishing prevention and ensuring that if they do get in, they’re contained. By training employees to recognize phishing and securing infrastructure against vulnerabilities, we help protect your organization from both the initial breach and the widespread damage that follows.

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Learning Objectives

Understand Phishing Tactics

Recognize URL Manipulation Techniques

Understand the Infrastructure Behind Phishing Attacks

Sections

Author

Joshua Crumbaugh
Social Engineer
Meet The Social Engineer

Joshua Crumbaugh

Recognizing the challenges and variation in applying psychology theory to real-world environments, I founded PhishFirewall, a security awareness and phishing training company built on these principles I’ve spent my career refining. We test and apply these concepts in diverse and practical ways to fit each organization’s unique needs.

I invite you to benchmark my company and discover how even slight changes in your approach can yield tremendous impacts on your organization’s security posture.

Hi, I’m Joshua Crumbaugh, and I’m proud to say that for over 20 years, I’ve been one of the leading Ethical Hackers in the United States. I’ve had the privilege of leading Red Teams for Fortune 500 companies, banks, governments, and large-scale enterprises, and and I routinely advises law enforcement agencies across the country and other industry leaders on emerging threats posed by human vulnerability.

The constant evolution of technology has advanced the tradecraft of exploiting people, but the good news is that people can be trained to become the most effective line of defense in any organization. Let’s work together to turn your people into your strongest line of defense.

What is PhishFirewall?

PhishFirewall is an emerging leader in people cybersecurity solutions designed to stop users from clicking on phish and empowers them to operate securely in the workplace.

AI autonomously delivers comprehensive awareness training and phishing simulations to optimize an organization's security posture and provides a one stop solution for industry specific compliance requirements. Unlike traditional tools, it provides zero campaign management, allowing administrators to strategically manage their priorities, with the added benefit of offering a streamlined, one-time setup with ongoing personalized training.
Key Benefits
Fully automate administrative management, reporting, and "just in time" communications.
Reduce organizational risk by 34% through customized training.
Increase employee engagement and performance by 42% without the punitive measures
“You set your people up in this system, and it just does it. It does it all."
– CISO, State Government
>80,000 Employees
“Once you see this in action, you can’t go back to the old way of training and testing.”
– CEO, Major Logistics Firm
>10,000 Employees
“This is security training 2.0, even the doctors do it!”
– CISO, Large Hospital
>30,000 Emoloyees

Key Features

Role-Based Phishing and Training

Tailor phishing simulations and training to each user’s role within the organization.

Customized Interaction and Testing

Adaptive training and testing based on individual performance and vulnerabilities for a personalized growth experience.

60-Second Training Modules

Quick, impactful training modules delivered in 60 seconds or less to fit seamlessly into your employees' day scaled at the frequency you want.

Complete Compliance Frameworks

Tailor phishing simulations and training to each user’s role within the organization.

Fast-Track Compliance

Accelerate your path to compliance with streamlined onboarding.

“Report a Phish” Button

Empower users to report suspicious emails with one click, improving overall security, speed of containment, and reduce the reach within the organization.

Multi-Language Delivery

Connect a global audience with training modules available in multiple languages.

Dual Coding Engagement

Enhance learning retention through dual coding techniques for better understanding and performance.

Extensive Training Library

Access a vast library of training materials that cover a wide range of security topics.

Customizable Training Modules

Create and deploy your own training modules to address specific needs within your organization.

Auto-Generated Reporting

Easily access automated reports that track progress and highlight areas for improvement.

User Report Cards

Provide individual feedback through user report cards, helping employees track their performance.

Organizational Leaderboards and Summaries

Foster healthy competition and track overall progress with organizational leaderboards and performance summaries.

Interactive Charts and Graphs

View trend analysis and performance distributions in real-time through dynamic, easy-to-read charts and tables.

Best-in-Class Administrative Dashboards

Manage your training programs effortlessly with intuitive, best-in-class dashboards designed for ease of use.

One-Day Setup

Get up and running quickly with a setup process that takes just a few hours.

Scalability

Effortlessly onboard new users and can be scaled to an organization of any size.

More In the Pipeline

We are always striving to innovate, and create the features that solve your problems!
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