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

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

These attacks often use information from social media, company websites, or other sources to make the email appear more legitimate and convincing. A spear phishing attack tricks users effectively into revealing sensitive information. As a result, spear phishing emails have been responsible for numerous data breach and financial losses.

Spear phishing attacks can cause damage to small businesses by manipulating users into downloading malware or giving away sensitive information through cloud services like Dropbox or Mailchimp. In these email attack types, the cybercriminal may send a fraudulent email that appears to come from a legitimate cloud service, but contains 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.

Here are some standard techniques attackers use to execute a spear phishing attack:

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 certain protected information.

Spear phishing attack types that use social engineering typically create 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 type that would heighten the importance of immediate action, 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 email attacks include posing as a trusted source, such as a colleague or a service provider, to gain the victim's trust. 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 obtained through other means, such as social media or data breaches, 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

This technique, called obfuscation, involves hiding the malicious code within a more extensive program that appears benign.

Obfuscation can be used in various ways in a spear phishing email attack. For example, a cybercriminal may send an email containing malicious and benign code attachments. The harmless code may be a legitimate document that the recipient will likely open, such as a PDF or Microsoft Office file. However, once the victim accesses 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 spear phishing attack types is through 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 includes a link to a website that looks like the actual site. However, the link 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 cyber thieves because it can help them evade detection by email security software. By mixing benign and malicious code, attackers can make it more difficult for antivirus software and other cybersecurity tools to identify and block the malicious code.

DocuSign Spear Phishing Email

Information Gathering

Information gathering is a common technique cyber thieves use to execute a spear phishing email attack in order to obtain valuable information and money. This involves gathering intel on the target, such as their name, position, email address, and any other details that can be used to personalize spear phishing emails and make them appear more convincing.

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

An attacker may email a target, pretending to be their supervisor and referencing the target's out-of-office message to make it appear that they know 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 in these types of email attacks may include:

• Researching the target on social media or professional networking sites.
• Searching for information about the target's employer.
• Using phishing emails to gather additional information from the target.

URL Manipulation

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

Minimal Text

A common technique cyber thieves use to execute spear phishing email attacks that will allow them to 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 being short and to the point, avoiding common spelling or grammar errors as well as preventing raised suspicion from the target

In a minimal text spear phishing email attack, the email may be short, typically only a sentence or two, and often includes a link or an attachment that the attacker wants the target to click on. The cybercriminal will use a tone of urgency by claiming the link or attachment has essential information that needs immediate action. This will convince the target to click on the link or attachment without considering the possible repercussions.

For example, this type of phishing attack will have phrases in the emails such as "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 a fake page designed to steal the target's login credentials or other sensitive information.

To protect against minimal text spear phishing email attacks, it is essential to be cautious when clicking links or downloading attachments from emails, especially if the email seems suspicious or 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 the legitimacy of the email and its contents before taking any action.

Spear Phishing Email Targeting BCMC GlobalCompromising API Tokens or Session Tokens

API and session tokens authenticate users and grant access to various services and applications. Cybercriminals can compromise these tokens during a spear phishing email attack.

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

For example, an attacker may send spear phishing emails 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 them and use them to acquire API or session tokens. Alternatively, the attacker may try to steal the tokens directly by exploiting vulnerabilities in the target's systems or applications.

Attackers can access the target's data and systems, such as stealing confidential data, spreading malware, or initiating fraudulent transactions, as a result of securing the tokens.

Cloud Service Manipulation

Attackers may use cloud services like DropBox to host malicious files or make the email appear more legitimate. They may use the services to host a malicious file and include a link in spear phishing emails.

To protect yourself from all of these spear phishing attack types, 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 sender's and email address's authenticity before responding or taking any action.

Why Is Microsoft Built-In Protection Not Enough?

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. Also, Microsoft 365 email security is not customizable to meet businesses’ security needs. This results in a limited ability to identify abnormal emails and social engineering attacks, thus leaving businesses vulnerable to account takeovers and targeted spear phishing attacks that often result in credential theft. 

Comprehensive additional 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 severe 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 involving sending fraudulent emails that appear to be from a known or trusted sender to obtain sensitive information. This type of phishing attack 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 at a time, spear phishing campaigns involve researching victims and using advanced intelligence strategies to compose just a thousand convincing messages.

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

To protect against spear phishing attacks, it is essential to be vigilant against spear 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 essential 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 cybersecurity tools to detect and respond to suspicious activities. By taking proactive measures to protect against token compromises and other types of phishing attacks, individuals and organizations can help prevent cyber thieves from obtaining valuable information and money through spear phishing attacks.

• Learn more about an effective email security software 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 company’s posture to protect against attacks and breaches by following best practices for email security.
• 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.