Email Security Gap Analysis: How to Find and Fix Gateway Vulnerabilities in 2026

In 2026, email gateways remain the primary line of defense for most organizations, yet research consistently shows that a significant proportion of malicious emails bypass even well configured secure email gateways. Industry analysis indicates that 82% of email based attacks bypass secure email gateways undetected, and that the majority of malicious emails originate from widely used cloud platforms including Office 365 and Google Workspace. These findings highlight a structural problem: organizations trust their gateways without testing them. Learn more: What Is Security Awareness Training.

Here are some recent statistics and examples that illustrate the financial, operational, and reputational impacts of email security gaps:

1. Business Email Compromise (BEC) attacks caused reported losses of over $2.9 billion in the United States in a single year, according to the FBI's Internet Crime Complaint Center, making it one of the costliest categories of cybercrime driven by email security gaps.
2. Industry breach reports indicate that over 40% of email based cyber incidents lead to operational disruptions, with ransomware events originating from phishing causing average downtime costs measured in thousands of dollars per minute.
3. High profile data breaches at major organizations in 2023 and 2024 stemming from email based attacks led to regulatory scrutiny, client losses, and reputational damage that extended well beyond the initial incident.

These examples underscore the critical need for email security gap analysis to safeguard financial stability, operational continuity, and organizational reputation.

This blog post will discuss how to use tools like the Email Threat Simulator to keep your emails safe from cyber threats. By adding the ETS to their security plans, companies can strengthen their defenses and stay ahead of cyber attacks.

Can Small Businesses Benefit from an Email Security Gap Analysis?

Absolutely! Small businesses often believe that their size may not attract cyber threats, but this is not the case. In fact, their often limited cybersecurity measures can make them attractive targets for cybercriminals. Conducting an email security gap analysis helps small businesses identify and fix vulnerabilities in their email systems.

This proactive step ensures they are less likely to fall victim to costly cyber attacks. By understanding and fortifying their defenses, small businesses can protect their assets, maintain customer trust, and support their overall growth.

If you want to test your email security gateways, Keepnet offers free testing and hardening of your email security in 2 minutes!

The Importance of Email Security Gap Analysis

An email security gap analysis is a key part of a company’s security strategy. It’s not just a one time task but an ongoing process integrated into the company’s overall cybersecurity efforts. This analysis compares your current security measures to industry best practices, showing where you stand and what needs improvement.

The gap analysis spots differences between your methods and the best ones out there. It finds weak spots in your email security gateway solutions, like human misconfigurations.

But it’s more than just spotting problems. The analysis also suggests ways to fix these issues. It gives you a plan to better secure your email, like fixing the misconfigurations, what to do for the bypassed malicious attacks, training employees, or setting up a solid response plan for incidents.

This process is important for staying ahead of cyber threats. It helps your organization to get ready against cyber risks and stop them before they become actual problems, rather than just dealing with them after they happen.

With cyber threats on the rise, having an email security gap analysis is no longer just nice to have; it’s a must. Using tools like the Keepnet’s Email Threat Simulator tool makes it easier to handle. This tool helps you find and fix vulnerabilities, boosting your email security, protecting important data, and keeping your digital communications safe.

How Often Should an Organization Conduct an Email Security Gap Analysis?

It is recommended that an organization conduct an email security gap analysis at least annually. However, more frequent analyses may be necessary depending on several factors such as the organization’s growth rate, changes in IT infrastructure, or an increase in cyber threats.

Benefits of Customizable Attack Simulations

Using customizable attack simulations is important for maintaining robust email security. By scheduling simulations to incorporate new and emerging attack vectors, you ensure that your security is always tested against the latest cyber threats. This proactive approach not only keeps your security up to date but also guides decisions on further technological enhancements needed for better protection.

Integrating with top tier Indicators of Compromise (IOC) and Exploitation Frameworks allows for a broad and current range of simulated attacks. This test checks your email system’s strength against various attack methods, from ransomware and browser exploits to malicious attachments.

Conducting these attack simulations sends 1000+ types of known and new threats to a test mailbox, critical for assessing how well your security infrastructure, like Microsoft’s, handles these attacks. This method is essential not just for finding gaps but also for planning improvements.

A thorough email security gap analysis does more than identify gaps; it provides a comprehensive review of your organization’s email security infrastructure. It adapts as your security needs and business goals evolve, offering a clear view of your current security posture and areas needing attention.

These insights establish an email security baseline, setting the standard for measuring effectiveness and tracking improvements. This baseline supports a tailored email security framework, which outlines specific strategies, policies, and procedures designed to boost your email security in line with your organization’s unique needs and risks.

Embedding this framework into your strategic planning ensures that your security measures align with your business objectives, integrating security as a fundamental aspect of your business strategy, not just an added feature. This alignment helps safeguard your organization as it pursues its goals, ensuring a secure operational environment.

Who Should Be Involved in the Email Security Gap Analysis Process?

The email security gap analysis process should involve a mix of key stakeholders to ensure comprehensive coverage. This includes IT security leaders, network administrators, and representatives from the compliance and governance teams. Including decision makers from various departments can also provide additional insights into how email security impacts different areas of the organization.

Additionally, it’s beneficial to involve external cybersecurity experts who can provide an unbiased view and highlight issues that internal teams might overlook. By involving a diverse group, businesses can ensure that their email security strategy is robust and inclusive of all necessary perspectives to protect their organization against cyber threats.

Exploring the Keepnet’s Email Threat Simulator (ETS)

Is your email security strong enough to stop new threats? How can you be sure your email defenses are working? With constant threats like spam, phishing, and ransomware, testing your email security is essential. Without regular checks, you risk letting hackers easily sneak through.

Email attacks cause most data breaches, costing businesses around $3 trillion each year. This massive loss shows why investing in strong defenses, like firewalls and anti spam tools, is critical. The Keepnet’s Email Threat Simulator (ETS) tool is designed to regularly check your email security gateways, find weaknesses, and fix them. This helps keep your defenses up to date and effective against cyber threats.

The ETS makes doing an email security gap analysis easy. Its advanced yet user friendly technology simplifies what used to be a complex task. By using the ETS, you can ensure that your email security measures are not just adequate but ahead of potential threats. This tool is essential for any organization serious about protecting its digital communications.

Email Bombing

The 'Email Bombing' feature of Keepnet’s Email Threat Simulator (ETS) is a critical test for assessing your email defenses. It sends hundreds of emails in minutes, simulating a common cybercriminal tactic. This test checks how well your security systems can handle intense loads of potential malware threats.

This test does more than just stress test your defenses. It also pinpoints their weak spots. It reveals what types of malware your current measures can't catch. Understanding these vulnerabilities is key to strengthening your email security.

Using the ETS for a security gap analysis is an important part of a strong email security strategy. It gives a clear view of your security status, shows where you are vulnerable, and guides improvements. Integrating this analysis into your strategic planning helps protect your organization from new and evolving cyber threats, ensuring your business remains secure as it grows.

Sync with Indicators of Compromise (IOC) and Exploitation Frameworks

The Keepnet’s Email Threat Simulator (ETS) stays current by syncing with leading Indicators of Compromise (IOC) and Exploitation Frameworks. It also uses manual sources to cover a wide range of attack types. This setup ensures ETS can simulate realistic attacks using over 240 different vectors, including ransomware, browser exploits, malicious code, and more. These simulations send threats to a test mailbox to evaluate your email system's defenses.

ETS offers thorough testing that goes deeper than just monitoring network traffic, which alone is not enough for comprehensive security. By performing real world attack simulations, ETS ensures your anti spam, antivirus, and other email security measures are effectively protecting against actual cybersecurity risks. This level of testing is important for maintaining strong defenses against sophisticated cyber threats.

Report, Remediation

The Keepnet’s Email Threat Simulator (ETS) is distinguished by its comprehensive reporting feature. This feature doesn't just list vulnerabilities; it delves into a detailed analysis of each security gap found in your email systems. The reports discuss the nature of these vulnerabilities, their potential impacts, and specific steps to mitigate them.

The reporting interface details all outcomes from the simulations. If an attack breaches your defenses, it is marked as 'failed', highlighting the need for immediate corrective action. ETS provides a checklist of remediation tasks to close these security gaps, helping you update critical systems like your firewall, anti spam filters, and Intrusion Prevention System (IPS).

ETS continuously generates new attack simulations based on a customizable schedule and the latest threat discoveries. This approach ensures your security measures are always tested against the most current cyber risks, providing you with the latest information and practical advice to enhance your technological defenses. This ongoing process of testing and updating is important for maintaining a robust email security posture.

What Sets Keepnet’s ETS Apart?

Keepnet’s Email Threat Simulator (ETS) stands out in the cybersecurity field for several key reasons:

• Comprehensive Real World Attacks: Find vulnerabilities in your secure email gateway by sending 1000+ real world attack vectors. This helps to pinpoint where your defenses might be lacking.
• Secure Your Email Gateways: Harden your Office 365, Google Workspace, and Secure Email Gateways (SEGs) for full protection. By testing these platforms, ETS ensures they can withstand the sophisticated attacks that are common today.
• Testing and Hardening Secure Gateway Solutions: ETS works with widely used secure gateway platforms including Microsoft 365, Google Workspace, and any standards based Secure Email Gateway (SEG). This ensures that your deployed platforms are properly tested against real attack vectors.
• Ease of Use: ETS is designed to be simple to set up with no need for complex installation or server configurations. This user friendly approach allows you to start securing your email systems quickly and efficiently.
• Comprehensive Testing: Unlike typical vulnerability scanners that only check network traffic, ETS examines your configurations for errors that could leave you vulnerable. It provides a more thorough evaluation of your email security posture.
• Real World Simulations: ETS conducts real world testing by simulating a wide range of attacks, including domain squatting and various malware threats like ransomware, browser exploits, and phishing attacks. This approach tests how well your systems would stand up against actual hacking attempts.
• Integration with Cyber Intelligence: ETS not only tests your defenses but also integrates with cyber intelligence services to ensure that it can simulate the most up to date attack vectors and tactics used by cybercriminals.
• Malicious Sample Testing: The simulator sends actual malicious samples to your test inbox to see how well your email filters and security protocols cope with threats such as ransomware and advanced persistent threats (APTs).

Try Keepnet Human Risk Management Platform, to look further gaps in employee training on social engineering attacks like phishing, SMS phishing (smishing), Voice Phishing (vishing), QR code phishing (quishing) or callback phishing.

Are you interested in seeing how the Email Threat Simulator works? Watch our demonstration below for a closer look at its capabilities.

Also, interested in seeing how to conduct phishing email analysis? Watch the YouTube video below that goes deeper into WordPress phishing email analysis.

Editor's Note: This article was updated on May 20, 2026.