Technology Advisor Blog



How AI is Making Phishing Attacks Smarter - What Small Businesses Must Do Now

Posted by Ann Westerheim on 5/14/25 9:48 AM

AI Blog-Phishing Attempts Happening to Many Folks

 

How hackers use AI for phishing attacks has become more advanced, making standard email security measures inadequate for protection. Modern cybercriminals leverage artificial intelligence to create convincing emails with flawless grammar, personal details from social media, and context-aware content that can deceive your most alert employees.  No more language barriers in cyber crime!

AI Blog-Risky Actions TakenResearch shows that 90% of cyber incidents begin with email, while 71% of users take risky actions online. Your business faces real threats from these AI-powered attacks, requiring smart security strategies that extend beyond basic email filtering. You'll learn practical ways to protect your company and team from these sophisticated phishing schemes.  The Verizon Data Breach Investigations Report (DBIR) and the ProofPoint State of The Phish Report are two "must read" reports that offer valuable insight into emerging cybersecurity trends.

The Evolution of AI-Powered Phishing Techniques

Email security has long been a very important part of any cybersecurity strategy, and phishing has been a technique that hackers frequently use to target their victims. The term "phishing" comes from the analogy of sending out a line and hoping to get back a fish, which is what hackers are doing. Some estimates suggest that about 90% of cyber incidents start with an email. This is where AI comes into play.

How AI Helps Hackers Create Convincing Phishing Emails

AI technology helps bad actors create emails that sound like they're from real people. They can use social media to make the messages more personal, piecing together information efficiently using AI to gather details and write convincing phishing content, including images and videos. By improving the quality of phishing lures, criminals around the world can write in perfect English, even if they are not native speakers.

In the past, phishing emails were often obvious, containing numerous typos, poor grammar, and disjointed content. However, today's phishing emails look sophisticated. When you're educating your employees to watch out for "suspicious" emails, it's important to consider what that means in the current landscape. An email written with perfect grammar and containing many personal details can be difficult to distinguish from a legitimate message.

The Role of Social Media in AI-Powered Phishing

AI makes it easier for criminals to send fake messages by gathering information from social media. Even though an email may contain a lot of pretexting, making it appear legitimate by including details about your work or recent events, it can still be a phishing attempt. These emails often blend in with your normal business activities.

A report by Proofpoint called "The State of the Phish" reveals some interesting statistics:

  • 71% of users admit to taking risky actions online, with 96% of them aware of the risks.
  • These actions include reusing passwords, clicking on unknown links, and using work devices for personal activities.

The idea that a criminal can enter your inbox like knocking on your front door, and an employee lets them in, is a significant concern.

 

Using AI for Good in Cybersecurity

While hackers use AI for phishing attacks, many cybersecurity protections for small businesses in the Boston area also employ AI for good. Take email security on Microsoft 365 as an example. We look for risky behaviors like logins from unknown locations. By using AI, we can piece together various signs of compromise and automatically shut down a mailbox when enough tripwires are triggered.

Phishing Prevention for Small Businesses

To protect your business from AI phishing, simply telling your employees not to click on suspicious emails is no longer sufficient. We recommend implementing more technology to test for phishing attempts. At Ekaru, we run simulated phishing tests to help educate and prepare employees.

Consider these alarming statistics:

  • 68 million malicious emails are sent just abusing the Microsoft brand, attempting to impersonate the company.
  • 85% of security professionals say employees are responsible for security, while 59% of employees either weren't sure who's responsible or claimed they are not responsible at all.

This disconnect highlights the importance of educating small businesses and helping them with phishing prevention to protect against AI-powered phishing attacks.

AI Blog-Phishing Brand Abuses - Microsoft in the lead

Small Business Vulnerability to AI Phishing

You might think that as a small business owner, your company's data isn't as valuable as that of larger enterprises. But here's the thing - any information your business holds can be used as leverage by hackers in attacks like ransomware. Sure, the amount of your data may be smaller, but it's still absolutely essential for running your business and protecting your employees and clients.

The Dangers of AI-Powered Phishing Attacks

Picture this: a hacker uses AI to create a phishing attack that looks identical to a real client communication. They're pulling logos and information from social media and your own website, making it incredibly easy for bad actors to cause harm.

Gone are the days when you could protect your business from AI phishing by simply telling employees not to click on suspicious emails. In the past, poorly written emails were a dead giveaway, but now AI can generate perfect English and grammar, slipping right past those email security filters you've set up.

Criminals are using AI to craft emails with so much detail that they seem completely legitimate. They're piecing together information to make these emails look like the real deal.

AI Blog-Why Risky Action is Taken

 

Why Small Businesses are Prime Targets

You might be wondering, why are small businesses the number one target for these attacks? A few reasons:

  • They often lack sufficient cybersecurity budgets.
  • They may not be aware of affordable measures to protect against cyber threats like AI phishing.
  • They may have implemented some steps but left gaps in their defenses.
  • Smaller organizations often lack the structure or operational maturity for comprehensive. cybersecurity awareness training for all employees.

Protecting Your Business from AI Phishing

To safeguard your business from AI phishing, consider implementing:

  • Simulated phishing tests.
  • Proper technology for scanning incoming emails to reduce risk.

But here's the catch - AI makes it much easier for criminals to bypass these protections. At the end of the day, it comes down to what the user does at their computer.

With many employees working from home, mixing personal and work tasks on the same devices, and connecting from insufficiently secured home networks, even your most well-intentioned employees could be your biggest risk.

The Importance of Payment Processing Security

Payment processing is a major area of concern. Implement DMARC protection for email security to make it tougher for bad actors to spoof your brand and send fake invoices to your clients.

Imagine the reputational damage if scammers create fake job postings or invoices in your company's name, even if the emails never originated from you. It's a nightmare scenario.

AI Blogs-Preception of Security Resonsibility

 

The Challenges of In-House IT for Small Businesses

Until your business has at least 100 employees, it may not make sense to have a dedicated in-house IT team. And even then, that person will need to be a jack of all trades and may not have the specific industry expertise needed in security, compliance, and staying up-to-date on the latest phishing prevention tactics for small businesses and how hackers are using AI for phishing attacks.  Often when we're working with local businesses in the Boston area, we'll see one person who gets designated as the IT point person, and they're trying to squeeze in IT support while also doing their full time "real" job.  There's no way to keep up!

Essential Small Business Phishing Prevention Strategies

To protect your business from AI phishing or any cyber threats, you need to implement both technical and non-technical measures. A company like Ekaru can provide smart and affordable phishing prevention solutions for small businesses.

Gateway Email Security Filter and Ongoing Monitoring

We typically recommend a gateway email security filter, as the NIST documentation on safe email suggests having both a gateway to prevent email from reaching your inbox and separate security measures for analyzing the email that does get through. This is important because hackers are using AI for phishing attacks to make them more convincing and harder to detect.

Ongoing security alert reporting is also recommended, whether you're using Microsoft 365 or Google Suite. The security measures in place monitor for risky behaviors, such as someone logging in from a new location or device. The software uses AI for good by analyzing various potential symptoms of compromise and can automatically lock down the mailbox if necessary. DMARC email security is another important measure that helps prevent others from spoofing your domain and protecting your reputation.

 

Cybersecurity Awareness Training and Simulated Phishing Tests

Cybersecurity awareness training is a key component of any cybersecurity program. Once you teach people about the possibilities, such as how hackers use AI for phishing attacks and the various phishing prevention techniques for small businesses, they are more likely to comply and not click on suspicious links out of curiosity.

Here are some key points to keep in mind:

  • Running simulated phishing tests can be an eye-opener for many, as people often think they won't fall for the trick, but there's always someone who does.
  • Create an open, positive, and supportive culture for cybersecurity, where people feel comfortable reporting suspicious emails without fear of criticism or blame.
  • Training sessions should always be educational and never a "gotcha" moment.

Multi-Factor Authentication and DNS Filtering

Multi-factor authentication is a must for businesses we work with in the Boston area and is one of the most important measures for phishing prevention. Even if someone gets hold of your password, they would still need the two-factor authentication code, which is specific and has a very short lifetime.

Keep in mind that while there are more sophisticated email attacks that rely on token harvesting and other techniques, no single security measure can offer 100% protection. The idea is to put different layers of security in place to improve your odds of not being the easy target for criminals.

Another baseline measure that Ekaru puts in place for all clients in the Boston area is DNS filtering. By implementing a few essential phishing prevention strategies and email security measures, you can eliminate a large portion of your cyber risk for a relatively low cost.

AI-Enhanced Protection Systems for Business Security

We're living in an age of rapid technological change, and AI is transforming the cybersecurity landscape for businesses of all sizes. Hackers are increasingly using AI to launch sophisticated phishing attacks, making phishing prevention a top priority for small businesses. But here's the good news: AI is also proving to be a powerful tool for protecting your business from these very same attacks.

The Advantages of AI-Based Security Systems

One of the key benefits of AI-based security systems is their ability to analyze multiple signals of compromise simultaneously, reducing the risk of false positives that can disrupt business operations. These systems can function like highly trained security experts, scanning emails for subtle signs of human compromise that might otherwise go unnoticed.

Imagine this scenario: you forward an article from your personal Gmail account to your work account. An AI-powered email security system might flag it as a potential impersonation attempt because the sender's name matches yours, but the email address is different. By highlighting such anomalies in different colors, these systems can help your small business stay protected online.

Effective Cybersecurity Measures for Small Businesses

Effective cybersecurity measures for small businesses should include:

  • Spam filters with AI detection.
  • Employee phishing simulation testing.
  • Thorough incident response protocols.

When a security incident does occur, it's essential to conduct a deep dive into how it happened and learn from the experience.

 

The Motivation of Cybercriminals

In today's digital landscape, cybercriminals are highly motivated by the potential financial gains of their attacks. They are increasingly using AI to enhance their tactics, making it essential for businesses to adopt a layered security approach that includes both technical and human safeguards. Simply telling your employees not to click on suspicious emails is no longer enough.

Protecting High-Risk Employees

Think about the risks faced by employees in accounts receivable and accounts payable, who regularly handle invoices and large dollar amounts. By implementing technical safeguards and providing adequate training, you can significantly reduce the risk of falling victim to an attack.

Proactive Measures for Early Detection

Proactive measures, such as DNS filtering, can also help detect attacks at an early stage. These systems work much like credit card fraud alerts, looking for unusual patterns and prompting users to confirm their actions.

Here's an example: if an employee appears to be accessing company resources from an unusual location, the system might ask if they are traveling. If the employee confirms they are on vacation, the activity can be validated. However, if they are sitting in the office, it could indicate a compromised account.

Simulated Phishing Tests and Consultations

If you're worried about your team falling for an AI-powered phishing scam, consider reaching out to a cybersecurity provider for simulated phishing tests. Many providers offer complimentary consultations to discuss your specific needs and concerns, even if you're not ready to engage their services immediately.

The Future of AI in Cybersecurity

As AI continues to evolve, both hackers and defenders will increasingly leverage its capabilities. While hackers are highly motivated by financial gains, businesses can stay one step ahead by implementing AI-powered defense tools and fostering a culture of cybersecurity awareness.

At the end of the day, the human element remains critical. Your employees will make the final decision on whether to click a link or not. By combining advanced technology with human vigilance, you can create a robust defense against even the most sophisticated AI-powered attacks.

 

Stay Protected and Productive with Expert IT Support and Security Solutions

Your business deserves strong protection against AI-powered phishing threats. Our team brings tested security solutions that match your budget and operations, helping you build effective defenses against advanced email attacks.

Concerned about AI phishing? Join me for a 15-minute Cybersecurity Power Chat - ask anything, no strings attached. Get expert insight even if you’re not looking for services right now.  We offer no-cost consultations to analyze your current security setup and recommend clear steps to protect your company data, reputation, and revenue.

Let's talk about how we can boost your email security and equip your team with smart tools to identify and block phishing attempts. Schedule a call with us today at 978-692-4200 or www.ekaru.com/contact-us.  

 

 

About the author:

Ann Westerheim - Ekaru - Cybersecurity

Ann Westerheim, PhD is the Founder and President of Ekaru, a Technology Service Provider of cybersecurity and IT services for small and medium businesses in the greater Boston area.  Ann is an accomplished technology innovator and leader with three engineering degrees from MIT.  She has twenty years of high tech experience in research, advanced development, product development, and as an entrepreneur. Her career has spanned a vast range of technology endeavors including research in thin film semiconductors and superconductors, microprocessor fabrication, development of early Internet medical applications, and now focusing on the application of technology in business. She has an avid focus on the "last mile" of technology and decreasing the digital divide.

https://www.linkedin.com/in/annwesterheim/ 

 

 

 

Topics: phishing, Cybersecurity, email scams, cybersecurity, cybersecurity training, Artificial Intelligence

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