The Anatomy of a Spear Phishing Attack: How Hackers Fool Their Targets

Spear phishing attacks are a type of targeted phishing attack in which cybercriminals send fraudulent emails to specific individuals or groups to obtain sensitive information or to gain access to computer systems or valuable information and money.

These attacks often use information gathered from social media, company websites, or other sources to make the email appear more legitimate and convincing. Spear Phishing attacks can be highly effective at tricking users into revealing sensitive information, and have been responsible for numerous data breach and financial losses.

Another way that spear phishing attacks can cause damage to small businesses is by manipulating users into downloading malware or giving away sensitive information through the use of cloud services like Dropbox or Mailchimp. In these attacks, the cybercriminal may send a fraudulent email that appears to come from a legitimate cloud service, such as a Dropbox file share or a Mailchimp newsletter. The email may contain a link or attachment that, when clicked, installs malware or redirects the user to a fake website designed to steal login credentials or other sensitive information.

Watch: Anatomy of a Spear Phishing Attack

Here are some common techniques used by attackers to execute a spear phishing attack.

What Are Common Spear Phishing Attack Techniques?

Social Engineering

Attackers use social engineering tactics to manipulate the victim into divulging sensitive information or taking a specific action. For example, they might impersonate a senior executive or a trusted vendor to request a wire transfer or sensitive information.

Spear Phishing attacks that use social engineering typically involve creating a sense of urgency or fear in the victim. For example, an attacker may send an email that appears to be from a bank, alerting the victim that there has been suspicious activity on their account and urging them to click on a link to verify their information. The email may also contain a threat, such as the implication that the victim's account will be frozen or closed if they do not respond.

Other common social engineering tactics used in spear phishing attacks include posing as a trusted source, such as a colleague or a service provider, to gain the victim's trust. For example, an attacker may send an email that appears to be from the victim's boss, asking them to transfer money to a specific account or provide sensitive information.

In some cases, attackers may use personal information that they have obtained through other means, such as social media or data breach, to make their spear phishing emails appear more convincing. For example, an attacker may use the victim's name or reference personal details to make the email appear more legitimate.

Obfuscation

DocuSign Spear Phishing EmailThis technique is called obfuscation, and it involves hiding the malicious code within a larger program that appears to be benign.

Obfuscation can be used in a variety of ways in a spear phishing attack. For example, an attacker may send an email that contains an attachment with both malicious and benign code. The benign code may be a legitimate document, such as a PDF or Microsoft Office file, that the recipient is likely to open. However, when the recipient opens the file, the malicious code is also executed, allowing the attacker to steal information or install malware on the victim's computer.

Another way that obfuscation can be used in a spear phishing attack is through the use of malicious links. An attacker may send an email that appears to be from a legitimate source, such as a bank or a social media site, and include a link to a website that looks like the real site. However, the link actually contains both benign and malicious code, and when the victim clicks on the link, the malicious code is executed.

Obfuscation is an effective technique for cyberthieves because it can help them evade detection by security software. By mixing benign and malicious code, attackers can make it more difficult for antivirus software and other security tools to identify and block the malicious code.

Information Gathering

Information gathering is a common technique used by cyberthieves to execute a spear phishing attack and obtain valuable information and money. This involves gathering information about the target, such as their name, position, email address, and any other details that can be used to personalize the spear phishing email and make it appear more convincing.

One common way that cyberthieves gather information is by using out-of-office messages. When someone sets up an out-of-office message, it usually includes information about their schedule, their contact information, and sometimes even their plans for the next few days. Cyber thieves can use this information to create a spear phishing email that appears to be from a colleague or supervisor, referencing the details from the out-of-office message to make it seem legitimate.

For example, an attacker may send an email to a target, pretending to be their supervisor, and referencing the target's out-of-office message to make it appear that they are aware of the target's schedule. The email may ask the target to perform a task, such as sending sensitive information or making a financial transaction, under the guise of a legitimate business request.

Other information gathering techniques used by cyberthieves may include researching the target on social media or professional networking sites, searching for information about the target's employer, or using phishing emails to gather additional information from the target.

URL Manipulation

Attackers may embed malicious links or URLs in the email that appear to be legitimate. When the victim clicks on the link, they are redirected to a fake website that looks legitimate, but is designed to steal sensitive information such as login credentials.

Minimal Text

Spear Phishing Email Targeting BCMC GlobalOne common technique used by cyberthieves to execute a spear phishing attack and obtain valuable information and money is to use minimal text in the emails they send. The idea behind this technique is to make the emails appear more legitimate by avoiding common spelling or grammar errors, and to avoid raising suspicion from the target by making the email seem short and to the point.

In a minimal text spear phishing attack, the email may be short, typically only a sentence or two, and often include a link or an attachment that the attacker wants the target to click on. The attacker may use a sense of urgency, such as claiming that the link or attachment contains important information that the target needs to act on immediately, in order to convince the target to click on the link or attachment without thinking.

For example, a common minimal text spear phishing attack might involve an email that simply says "Click here to view important information." The email may appear to come from a legitimate source, such as a bank or other financial institution, and the link may lead to a webpage that looks similar to the legitimate site, but is actually a fake page designed to steal the target's login credentials or other sensitive information.

To protect against minimal text spear phishing attacks, it is important to be cautious when clicking on links or downloading attachments from emails, especially if the email seems suspicious or if it comes from an unknown source. It can also be helpful to hover the mouse over links before clicking on them to verify that the URL matches the expected destination, and to verify the legitimacy of the email and its contents before taking any action.

Compromising API Tokens or Session Tokens

API tokens and session tokens are used to authenticate users and grant access to various services and applications. One common technique used by cyberthieves to execute a spear phishing attack and obtain valuable information and money is to compromise these tokens.

In this type of attack, the cyberthief may attempt to steal API or session tokens through a phishing email or other means. Once they have obtained the tokens, they can use them to gain unauthorized access to the target's accounts, systems, or applications, and steal sensitive information or carry out other malicious activities.

For example, an attacker may send a spear phishing email with a link to a fake login page that looks like a legitimate site. If the target enters their login credentials on this page, the attacker can capture the credentials and use them to obtain API or session tokens. Alternatively, the attacker may try to steal the tokens directly by exploiting vulnerabilities in the target's systems or applications.

Once the attacker has obtained the tokens, they can use them to gain access to the target's data and systems, and carry out activities such as stealing confidential data, spreading malware, or initiating fraudulent transactions.

Cloud Service Manipulation

Attackers may use cloud services to host malicious files or to make the email appear more legitimate. For example, they may use a service like Dropbox to host a malicious file and include a link to the file in the email.

To protect yourself from spear phishing attacks, it is essential to be vigilant and cautious when opening emails or clicking on links, especially if they are unsolicited or appear suspicious. Always verify the authenticity of the email and sender before responding or taking any action.

Microsoft 365 built-in protection is limited and full of gaps that can lead to successful spear phishing attacks. Protection is status, single-layered, and fails to detect new and emerging threats. Additionally, Microsoft 365 is not customizable to meet businesses’ unique security needs. This results in a limited ability to identify anomalous emails and social engineering attacks, leaving businesses vulnerable to account takeovers and targeted spear phishing attacks that often result in credential theft. 

Why Is Microsoft Built-In Protection Not Enough?

Proactive, multi-layered supplementary email security defenses like Guardian Digital EnGarde Cloud Email Security close these critical loopholes in Microsoft 365 protection that are the source of many of the most serious attacks today. EnGarde is constantly learning from and adapting to the threats that challenge it, and updating its protection in real-time to remain ahead of emerging threats to prevent future attacks.

Microsoft 365 built-in protection is limited and full of gaps that can lead to successful spear phishing attacks. Protection is status, single-layered, and fails to detect new and emerging threats. Additionally, Microsoft 365 is not customizable to meet businesses’ unique security needs. This results in a limited ability to identify anomalous emails and social engineering attacks, leaving businesses vulnerable to account takeovers and targeted spear phishing attacks that often result in credential theft. 

Proactive, multi-layered supplementary email security defenses like Guardian Digital EnGarde Cloud Email Security close these critical loopholes in Microsoft 365 protection that are the source of many of the most serious attacks today. EnGarde is constantly learning from and adapting to the threats that challenge it, and updating its protection in real-time to remain ahead of emerging threats to prevent future attacks.

Keep Learning About Advanced Spear Phishing Techniques

Spear phishing is a highly targeted version of phishing that involves sending fraudulent emails that appear to be from a known or trusted sender in order to obtain sensitive information. Spear phishing is becoming increasingly common because it is generally even more successful than conventional phishing in deceiving recipients. As opposed to sending hundreds of thousands of relatively generic emails out at a time, spear phishing campaigns involve researching victims and using advanced intelligence strategies to compose just a thousand or so convincing messages.

Spear phishing can be seen as a cyber crime double-play - threat actors have the ability to compromise the identity of one business and then use it to steal sensitive information from another.

To protect against spear phishing attacks, it is important to be vigilant against phishing emails and other forms of social engineering, and to avoid clicking on links or downloading attachments from unknown or suspicious sources. It is also important to use strong, unique passwords and enable two-factor authentication wherever possible, as this can help prevent attackers from accessing accounts even if they have stolen tokens.

In addition, organizations can help prevent API and session token compromises by implementing security measures such as regular vulnerability scanning and patching, limiting user access to sensitive systems and data, and using monitoring tools to detect and respond to suspicious activities. By taking proactive measures to protect against token compromises and other types of attacks, individuals and organizations can help prevent cyberthieves from obtaining valuable information and money through spear phishing attacks.

• Learn more about an effective email security solution that understands the relationships you have with other people while gaining a deeper knowledge of the types of conversations you have with them.
• Prepare your business for cyberattacks to make sure employees stay safe online.
• Improve your email security posture to protect against attacks and breaches by following best practices.
• Keeping the integrity of your email safe requires securing the cloud with spam filtering and enterprise-grade anti-spam services.
• Get the latest updates on how to stay safe online.