The landscape of cybersecurity is evolving, so modern threats like SMTP smuggling are a stark reminder of the importance of staying up to date on defending against such cyberattacks. But what is SMTP smuggling, how does it work?

What is Simple Mail Transfer Protocol?

Simple Mail Transfer Protocol is a TCP/IP network protocol utilized to send emails between different servers. SMTP email clients include Gmail, Outlook, Yahoo, etc.

Basically, after an email is composed, using a client such as Gmail or Outlook, it is delivered to an SMTP server, which verifies the recipient’s domain to find the appropriate email server to deliver the email to. The SMTP server at the recipient’s domain processes the email, and either delivers the message or uses SMTP to forward it via another network before delivery.

What is SMTP Smuggling?

Security is the biggest problem with the Simple Mail Transfer Protocol because it lacks authentication. With the right tools, hackers can simply choose the sender’s name, so that their messages appear to have been sent from legitimate sources. They try to convince the recipients to take specific actions, such as clicking phishing links, downloading files infected with malware, sending sensitive information, etc.

The goal is to trick the recipient’s server into a different interpretation of the end of a message using SMTP commands so that the email appears as two separate messages.

How Does SMTP Smuggling Work?

To perform such attacks, hackers “smuggle” ambiguous SMTP commands to eventually compromise the integrity of the email-server communications. Basically, SMTP servers usually indicate the end of message data with the code <CR><LF> also known as “Carriage Return” and “Line Feed” or “\r\n.\r\n”. These are the standard text delimiters.

By changing this code sequence, hackers can alter the server’s understanding of where the message data ends. This creates an opportunity for smuggling extra data.

Spoofed emails are usually just a part of targeted phishing attacks. Organizations are particularly vulnerable to SMTP smuggling because it can be easy to spoof their domains and use social engineering to send phishing emails or launch spear-phishing attacks.

How to Avoid SMTP Smuggling Emails

Manufacturing companies of the most popular mail servers, such as Postfix, Exim, and Sendmail have released solutions to defend against SMTP smuggling. Several other measures can be taken to minimize the threat.

We strongly advise running regular IT security checks on your organization’s infrastructure to monitor possible attack vectors and vulnerabilities.

Check the email-routing software being used. If the software is known to be vulnerable, update it to the latest version and use settings that specifically reject unauthorized additions.

Conduct security awareness training regularly, teach employees how important it is to always verify the sender’s email address and full name before proceeding with any actions.

What Does SMTP Email Spoofing Look Like?

To be alert to the threat of SMTP smuggling, it is critical to know what a spoof email might look like. A spoof email may take several forms.

There is the case of display name spoofing, where the sender’s name is spoofed, most times by using the real name of an organization’s employee. Most email clients automatically hide the sender’s email address and show the full name next to “From:”, which is why recipients should always check the email address to make sure it corresponds to the sender’s name to prevent downloading suspicious attachments, clicking links, or replying to deceitful emails.

Lookalike domain spoofing is a more complex cyberattack because it requires the perpetrator to register a domain like that of the target organization, set up the e-mail service, etc. There are two similar approaches that hackers take to domain spoofing: a misspelling of a legitimate company domain and Unicode Spoofing, where hackers replace an ASCII character in the domain name with a similar-looking character from Unicode.

At StratusPointIT we help organizations defend against various types of cyber threats, such as spoofing attacks. For more relevant information, or for a cybersecurity audit, please reach out to us.

As information security threats are multiplying, security measures are multiplying too.

Employees are regularly informed of more threats to watch out for and more security policies to follow, creating additional workflows and distractions for their already busy days. This is very likely to have an impact on their daily tasks. For instance, just a simple task like reading a new email can take twice as long as the recipient will probably double check if the attachment is safe before opening it.

Consequently, employees can experience reluctance to deal with computer security. Being overwhelmed by security policies can lead to lower levels of security and higher risks for the organizations.

Why is it happening?

People generally agree that security is crucial, but some of them fail to comply for several reasons.

While security is a top priority for security professionals, many employees are focused on productivity and getting their job done. If the security measure is making it harder to complete a task, some employees can perceive the measure negatively, and while balancing between security and productivity, the wrong decision can be made.

However, it can also be unintentional. For example, some people may not be aware of certain security policies, a consequence of having too many policies to keep track of.

Also, the level of self-control decreases when more decisions need to be made in a short interval. If the users are required to make numerous security decisions during their workday, they are more likely to make poor decisions.

The Impact

Security fatigue has a direct impact on the organization’s security and in some cases, it may affect productivity.

Therefore, risk mitigation is less effective, and the organization might be vulnerable to cyberattacks and data breaches. In some unfortunate cases, this may result in:

• Credentials being stolen because phishing training was skipped.
• Data being shared with unauthorized individuals because a colleague requested it.
• Malware installation because a warning was dismissed.
• Login information being breached after a brute force attack because an easy password was chosen.

The Solutions

Security policies are necessary to secure the organization and to be compliant with security standards and legislation.

• When it has been decided a security policy is required, make sure it is easy to follow for your employees. It should be crystal clear what is expected of employees.
• The communication around policies should include less jargon and more clarity.
• Make sure security policies are based on risk assessment. Acknowledge which risks are acceptable to your organization and which are not.
• When assessments must be done by an employee, offer support in making these decisions, for instance, provide a guideline to determine if and why an email has clear indicators of phishing or malicious vectors.
• Security policies should have a clear purpose. Explaining the risk that is mitigated and the possible impact on the organization or individual is crucial.
• Security teams usually share information around security policies annually via specific awareness sessions. The problem with this approach is that people tend to forget what has been communicated. Therefore, it would be wise to repeat the message frequently.
• What is even more effective is sharing the policy or guideline in a timely manner, preferably in the moment the employees need to be aware of it. For example, an instant warning informing users they may be visiting a malicious website or that sensitive information was found in an email attachment. This will lower the risk and the burden of having to remember complex rules and regulations, improving the security of your organization.
• Partner with a trusted IT support provider to ensure that your business stays secure, and your systems are up to date.

Conclusion

Security awareness should be a joint, regular effort. Thinking that what you are doing is simply not interesting for hackers and assuming your organization won’t be targeted is dangerous. No organization is safe from malicious actors.

To overcome the risk of security fatigue, organizations should make sure their security policies are proportional and efficient.

This type of cyberattack occurs when the perpetrator gains illegitimate access to your organization’s digital infrastructure just by utilizing a third-party system (provider or partner) that is already connected to your infrastructure.

Basically, because the third party has been granted the rights to use and modify areas of your network, your applications, or sensitive data, the hacker has to penetrate the third party’s defenses to infiltrate your system.

Software supply chains are vulnerable because modern software is not written from scratch. It involves many pre-existing components, such as third-party APIs, open-source code, etc.

Supply chain attacks are diverse, often impacting large companies, as was the case last year with Okta and JetBrains in October, Norton in May, and Airbus in January.

How Do Supply Chain Attacks Work?

For a successful supply chain attack, hackers must find ways to either insert malicious code into software or compromise network protocols.

Many of the products or services that get compromised come from trusted vendors making it easier for supply chain attackers to infiltrate the targeted systems, underscoring the value of attacking the supply chain. Ironically, they may do so using software updates which are often designed to mitigate security vulnerabilities.

Therefore, supply chain attacks are some of the most difficult threats to prevent because they take advantage of inherent trust. Mitigating and remediating a supply chain attack isn’t as simple as installing an antivirus or resetting your operating system because these attacks are usually well disguised.

Common Sources of Supply Chain Attacks

Commercial software

Because hundreds of organizations may use the same software solutions, a supply chain attacker who penetrates a software company’s system or compromises the integrity of their product can eventually gain access to a great number of targets.

Open-source software

When it comes to open-source software solutions, any developer can contribute to the making of a program. Using this free access, hackers may implement vulnerabilities into open-source solutions.

Even though other members of the development community can see and evaluate the code deployed by perpetrators, they may not know what to look for, allowing hackers to initiate a variety of vulnerabilities.

Foreign-sourced software

In some countries where the government exercises granular control over what certain private companies produce, software products may contain malicious code allowing the beneficiary to understand more about the targets’ systems.

Types of Supply Chain Attacks

Based on the targeted software, there are several types of attacks, all of which involve creating or exploiting security weaknesses.

Compromised software development tools – attackers utilize these tools to implement security weaknesses in the development process.

Preinstalled malware – hackers introduce malware on mobile devices such as smartphones, cameras, etc., and when the target connects the infected device to a system or network, the malicious code is activated.

Stolen certificates – that perpetrators use to disguise malicious code under the appearance of a company’s certificate.

Compromised firmware – attackers can include malicious code in firmware to gain illegal access to a system.

The Supply Chain Security

Such cyberattacks are very sophisticated, therefore organizations often employ the power of behavioral-based analysis to determine indicators of attack to successfully defend their assets.

Mitigating the risks is paramount, consequently you should consider utilizing advanced security solutions such as Security Information and Event Management (SIEM) solutions along with a Security Operations Center (SOC) which include 24/7 intelligent threat detection systems which collects logs, makes statistical correlations, analyzes threat alerts across your network, combines data from several different sources to help security teams remediate issues in a timely manner.

In some cases, all relevant analytics, threat intelligence, and forensic data should be passed to professional analysts, who classify alerts and determine the appropriate response to reduce the risks/effects of incidents. This is known as managed detection and response (MDR).

These services combine threat intelligence, advanced analytics, and human expertise in security incident discovery, investigation, and response deployed at the host and network levels to help keep your organization secure and reduce the ability for malicious activities to move laterally in your environment.

Enhance your readiness with proactive services to improve not only the supply chain security, but your organization’s overall security posture. For more information, please reach out to us. A member of our team will get in touch with you in one business day.

All your business processes, technologies, and business operations involve inherent security risks, and your organization is the only one responsible to make sure those risks are both acknowledged and addressed.

Regardless of the size of your organization, the need for a technology security risk assessment is obvious because the threat is imminent. Many organizations do not have one performed, exposing their assets to cyber-attacks.

Who Should Perform a Cyber Risk Assessment?

The process requires organizational transparency, typically provided by internal teams. However, organizations with no skilled personnel can outsource risk assessment to a third party.

An in-house team will include technicians and engineers with a deep understanding of the organization’s network infrastructure and flows of information for any process or system.

Why Perform a Security Risk Assessment?

Protects Your Reputation

Without regular assessments, the danger of security breaches is high, putting your organization’s reputation on the line with clients and vendors for not adequately protecting their data against an attack. This would affect your reputation and impact the potential of your business.

Avoid Security Breaches

Regardless of how sophisticated your systems are, your organization will always be a target for cyber criminals. Hackers are constantly looking for fraudulent means to take advantage of any vulnerabilities in your system.

Performing frequent risk assessments can help your team identify security issues and ensure that relevant policies and controls are put in place before a breach.

Keeps Systems Updated

Security protocols are always changing, and your organization’s technologies and processes are changing as well. Conducting security risk assessments regularly allows you to consolidate the state of security of your business.

Reduces Costs

Depending on the size of your organization, a breach can cost you thousands of dollars or even more just to get your data back and business operations up and running.

However, there is the cost associated with clients leaving or time spent reassuring clients. All those costs mentioned are usually unplanned expenses and can become a heavy burden to your budget. A security risk assessment allows you to plan and reduce such costs.

Avoid Violations

Organizations that handle sensitive data, such as protected health information, are required to abide by security and privacy laws. Failing to perform a security risk assessment is a violation of these regulations.

Also, if a breach does occur, there is the potential of fines and long and costly lawsuits. One of the easiest ways to avoid non-compliance is by performing a security risk assessment.

Increase Self-Awareness

Another major benefit of such an assessment is the ability to provide you with a detailed report about your network and how it is being utilized. This could also highlight inefficiencies within your network that could be costing you money and could be easily streamlined with an adequate solution.

An IT security risk assessment can help identify exploitable vulnerabilities that your team might not be aware of. Unfortunately, without proper insight over their network, an organization cannot efficiently secure its infrastructure against an attack.

A Culture of Safety

Creating a culture of safety should be more than just a legal requirement. As an organization, it is your responsibility to build an environment where your staff and customers feel safe and valued.

Developing skills for identifying, analyzing, and evaluating security risks is crucial. Therefore, investing in security risk assessment training will help your organization in the long run.

NOTE: Cybersecurity awareness training can serve as a starting point for empowering workers with a clearer understanding of security risks.

As you can see, there are several benefits to an organization for having regular security risk assessments performed. Our seasoned team has the necessary resources to provide you with top-notch cyber risk assessment, security awareness training, network security services, and more.

Data loss prevention (DLP) includes tools, processes, and policies specifically used to ensure that sensitive information is not lost, leaked, or misused.

DLP tools help classify data and identify violations of predefined policies. Once identified, DLP enforces remediation, it triggers alerts, utilizes encryption, and other actions to prevent users from accidentally or maliciously sharing data that could expose organizations.

DLP Adoption

According to Gartner Magic Quadrant for Enterprise DLP of 2017, Gartner estimated DLP market would reach USD 1.3 billion in 2020. In 2022, Grand View Research – DLP Market Size and Share Report estimated the global data loss prevention market at USD 1.8 billion and expects an annual growth rate of 22% until 2030.

The data loss prevention market has evolved, now it includes cloud storage, complex security services, such as advanced threat protection, multi factor authentication, etc.

The massive uptick in DLP adoption is not accidental. Here are the main reasons that are driving the wider adoption of data loss prevention programs:

• Nowadays, there are more places that require protection, such as multiple cloud platforms, complex networks and services which make data protection processes more difficult.
• Global data protection regulations constantly change, usually tightening data protection requirements.
• Data breaches are more frequent, potentially exposing a lot more data as people and organizations rely on technology more than ever.
• Stolen data is worth more.

DLP Best Practices

Determine your main data protection objective.

Are you trying to protect your intellectual property or meet regulatory compliance? Having a clear understanding will allow you to easily determine the most appropriate DLP architecture.

When searching for DLP solutions, cover as many aspects as possible.

• What types of deployment architectures are offered?
• Do you need to defend against both internal and external threats?
• Will users be able to self-classify documents?
• Are you interested in protecting mainly structured or unstructured data?
• What compliance regulations are you bound by? Are there any industry-specific standards?
• How quickly do you have to implement your DLP program?
• Will you need additional staff to manage your program?
• What technologies would you like to integrate with your DLP?

Also, a comprehensive DLP solution will provide the IT security team with complete visibility into all data on the network:

Data in use: Protecting data being used by an application or endpoint through user authentication and access control.

Data in motion: Securing transmission of sensitive information while it moves across the network.

Data at rest: Protecting any network-stored data including cloud through access restrictions and user authentication mechanisms.

Always collaborate with all business units and with your IT security provider to define the DLP policies that will govern your organization’s data. This will ensure that all business units are aware of the policies in place.

Define success metrics and share results with business executives. Determine measurable key performance indicators and monitor them closely to determine the efficiency of your DLP program and areas of improvement.

Contextualize suspicious attempts to strengthen prevention measures and remediation activities.

Document your processes carefully. This will help you implement policies consistently, give you a document of record for when reviews are needed, and will also be necessary when onboarding new team members or employees.

Perform regular audits to ensure that your DLP program is working as intended.

Conclusion

DLP is a program, not a product. Observing how users, systems, and events interact is crucial for data protection. Understanding that DLP is a constant process to be continuously worked on will help you achieve long-lasting success.