Man in the Middle (MITM) Attack Examples: 3 Worst Attacks

By Tibor Moes / Updated: June 2023

Man in the Middle (MITM) Attack Examples: 3 Worst Attacks

Man in the Middle (MITM) Attack Examples

Imagine you’re sending a letter to a loved one. You place it in your mailbox for the postman to collect. But instead, a sneaky neighbour snags it first, reads it, alters some words, and then passes it along as if nothing happened. This is akin to the invisible treachery of a Man in the Middle attack.


A Man in the Middle attack is when a hacker intercepts and possibly alters communication between two parties without their knowledge, much like a deceitful intermediary in a conversation.

Example 1: WiFi Pineapple (2008 onwards). The WiFi Pineapple, developed by Hak5, is a hacking device that makes Man in the Middle attacks frighteningly simple. It tricks wireless devices into connecting with it by posing as a trusted network. Once connected, the attacker can spy on, manipulate or block your internet activity.

Example 2: The Iranian Gmail Hack (2011). In 2011, hackers allegedly backed by the Iranian government used an MITM attack to spy on citizens’ Gmail accounts. They fooled users by using a fake, yet convincing, SSL certificate which made the malicious site appear like the real Gmail login page.

Example 3: The Great Cannon (2015). China’s “Great Cannon” is a separate offensive system that intercepted web traffic to or from China’s largest search engine, Baidu. It used MITM techniques to inject malicious scripts into users’ browsers, effectively weaponizing the browsers against specific websites, including GitHub.

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Man in the Middle (MITM) Attack Examples In-Depth

WiFi Pineapple (2008 onwards)

Let’s journey into the world of the internet for a bit. It’s kind of like a big city. You have your home (your device), your friends’ homes (other devices or servers), and the roads you take to visit them (the internet). Now, imagine if a charismatic stranger sets up a free, delicious pineapple juice stand in the middle of your route. You stop by, enticed by the offer, unknowingly stepping into a trap. In the digital world, this clever trap is what we call the WiFi Pineapple.

The WiFi Pineapple, launched by Hak5, is a curious little device. It’s a bit like that “too good to be true” pineapple juice stand, as it tricks your device into believing it’s your trusted home WiFi network. Just as you’d eagerly stop for the refreshing drink, your device automatically connects to the WiFi Pineapple, thinking it’s your safe home WiFi.

But how does the WiFi Pineapple manage this trick? Well, when your device is not connected to WiFi, it sends out signals, much like calls, searching for familiar networks. The WiFi Pineapple responds to these calls saying, “Hey, I’m your trusted network!” and your device, being none the wiser, connects to it.

Once you’re connected, the person controlling the WiFi Pineapple stands between your device and the actual internet – the Man in the Middle. Think of it like that stranger at the juice stand eavesdropping on your phone conversations and even adding their own spin on your words. They can spy on your internet activity, block certain websites, or even change the content you see online. Scary, right?

Since its debut in 2008, the WiFi Pineapple has become a favored tool among hackers and cybersecurity professionals alike. It’s a stark reminder of how important it is to be cautious when connecting to public WiFi networks. As tempting as free pineapple juice – or free WiFi – might be, it’s always safer to stick to your known and trusted sources.

So next time you’re out and about with your device, remember the WiFi Pineapple. Be careful about the networks you connect to. After all, not every free pineapple juice stand – or WiFi network – is what it seems!

The Iranian Gmail Hack (2011)

Now, picture this. You’re in a bustling city, about to enter a building you know well — let’s call it the Gmail Building. Outside, it looks the same. The doorman — or the login page — is also familiar. So, you hand over your ID — your login details — without a second thought. But, unbeknownst to you, the building isn’t what it seems, and the doorman isn’t who you think he is. Welcome to the 2011 Iranian Gmail Hack.

Back in 2011, something very similar happened to countless Iranian citizens. They thought they were logging into their Gmail accounts, but they were unknowingly walking right into a trap. What looked like the regular Gmail login page was, in fact, a duplicitous impostor — the handiwork of hackers allegedly supported by the Iranian government.

These hackers pulled off a Man in the Middle attack by using a fraudulent SSL certificate. Now, an SSL certificate is kind of like a doorman’s uniform. It’s what assures you that you’re entering a safe, secure building — or website. In this case, the hackers had a fake uniform, fooling people into believing they were in the right place.

Once users entered their login details on this fake page, the hackers had them. They could read their emails, access their contacts, and basically snoop around in their personal accounts. Imagine having a stranger invade your home, reading your personal letters and rifling through your address book. That’s exactly what happened to these users, but in the digital space.

What’s even more startling is that the hackers didn’t just stop at stealing information. They also had the power to alter it. They could change the contents of emails or even send new ones on behalf of the user. It’s like the rogue doorman taking your keys, entering your apartment, and wreaking havoc without you being the wiser.

The Iranian Gmail Hack of 2011 was an unnerving episode that showed how even sophisticated systems like Gmail could be compromised using MITM techniques. It also underscored the importance of vigilance and the need for advanced security measures to ensure our virtual homes — our online accounts — remain safe and inviolable.

So, the next time you log into an account, spare a thought for the digital doorman. Make sure he’s wearing the right uniform. And remember — not all that looks familiar on the internet is genuinely what it seems.

The Great Cannon (2015)

Imagine for a moment you’re on a massive highway, like the ones you see in movies — wide lanes, smooth surfaces, and cars speeding along. This highway is the internet, and you’re on a journey to your favorite website, let’s say, an online library named Baidu. Out of nowhere, an invisible cannon pops up in the middle of the road, redirecting your car towards a place you didn’t intend to go. Sounds dramatic, right? But, in the virtual world, this was exactly the scenario with China’s Great Cannon in 2015.

The Great Cannon isn’t a physical weapon, but a powerful digital one. It’s like a menacing roadblock on the internet highway that can intercept and alter the traffic to and from China’s biggest search engine, Baidu.

So, how does it work? Well, let’s go back to our highway analogy. When you use the internet, your device sends out requests — like a car on a journey. These requests travel through various checkpoints before reaching their final destination. But the Great Cannon can interrupt this journey. Like a manipulative traffic officer, it seizes some of these requests and re-routes them.

But the Great Cannon doesn’t stop there. Once it catches your requests, it can also alter them. In the real world, it’s as if the traffic officer jumped into your car, changed your destination in the GPS, and sent you off on a completely different path.

In 2015, this digital weapon was used to weaponize users’ browsers against specific websites. This means that the Great Cannon didn’t just change the destination of the requests, but it also loaded them with digital ‘ammo’. This ‘ammo’ was in the form of malicious scripts, which were used to barrage and overwhelm certain target sites, like GitHub.

The Great Cannon’s power is alarming because of the sheer volume of internet traffic that flows through Baidu — much like a busy highway during rush hour. The potential to disrupt, control, or damage is immense and brings home the significance of cybersecurity in our digital landscape.

So, the next time you head off on an internet journey, remember the Great Cannon. It’s a reminder to all of us to be conscious of the roads we travel online. In the vast highway of the internet, it’s important to ensure our vehicles — our devices — are secure, and we’re aware of the checkpoints we pass through.


In the labyrinth of the internet, Man in the Middle attacks are like invisible minotaurs waiting to pounce. We’ve seen how tools like the WiFi Pineapple, events like the Iranian Gmail Hack, and systems like the Great Cannon can intercept and alter the communication happening on the internet. These are stark reminders of the digital age’s perils. But don’t despair. Awareness is the first step toward prevention. By understanding these risks, we can learn how to protect ourselves and navigate the online world more safely. In the end, while the internet can sometimes seem like a hostile environment, remember that you’re not alone in this journey. We’re all in it together, learning, growing, and hopefully, staying one step ahead of the hackers.

How to stay safe online:

  • Practice Strong Password Hygiene: Use a unique and complex password for each account. A password manager can help generate and store them. In addition, enable two-factor authentication (2FA) whenever available.
  • Invest in Your Safety: Buying the best antivirus for Windows 11 is key for your online security. A high-quality antivirus like Norton, McAfee, or Bitdefender will safeguard your PC from various online threats, including malware, ransomware, and spyware.
  • Be Wary of Phishing Attempts: Be cautious when receiving suspicious communications that ask for personal information. Legitimate businesses will never ask for sensitive details via email or text. Before clicking on any links, ensure the sender's authenticity.
  • Stay Informed. We cover a wide range of cybersecurity topics on our blog. And there are several credible sources offering threat reports and recommendations, such as NIST, CISA, FBI, ENISA, Symantec, Verizon, Cisco, Crowdstrike, and many more.

Happy surfing!

Frequently Asked Questions

Below are the most frequently asked questions.

What can I do to protect myself from Man in the Middle attacks?

To protect yourself, it’s vital to always use secure networks when handling sensitive information. Public WiFi networks can be easily exploited for MITM attacks. When surfing the web, look for the HTTPS prefix in the web address. This ‘S’ stands for secure, meaning communication with the website is encrypted. Also, regularly updating your device’s software can help patch any security vulnerabilities.

How can I tell if I am a victim of a Man in the Middle attack?

Detecting an MITM attack can be challenging as they are designed to be stealthy. However, some signs can indicate a potential attack. If your device frequently disconnects from the internet, or your battery drains more quickly than usual, it may be due to a hacker’s activity. Also, pay close attention to website certificates when browsing, as a warning sign or lack of HTTPS may indicate a rogue site.

Are Man in the Middle attacks only a concern for computers?

Not at all. Any device that connects to the internet — smartphones, tablets, even smart home devices — can be potential targets for a MITM attack. As our world becomes more connected, the need for robust cybersecurity measures spans across all digital devices.

Author: Tibor Moes

Author: Tibor Moes

Founder & Chief Editor at SoftwareLab

Tibor is a Dutch engineer and entrepreneur. He has tested security software since 2014.

Over the years, he has tested most of the best antivirus software for Windows, Mac, Android, and iOS, as well as many VPN providers.

He uses Norton to protect his devices, CyberGhost for his privacy, and Dashlane for his passwords.

This website is hosted on a Digital Ocean server via Cloudways and is built with DIVI on WordPress.

You can find him on LinkedIn or contact him here.

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