Category Archives: Cybersecurity

Small businesses are the most common ransomware target by volume of incidents, even though many small business owners assume hackers focus on larger organizations. A 22-person company has enough revenue to be worth attacking, no dedicated security team to defend it, and a publicly traceable footprint that takes about an hour to research.

What follows is a step-by-step walkthrough of how a small business gets attacked, written from the attacker’s side. The company in this account is composite, but the methods are accurate to current threat intelligence reporting. After the walkthrough, you’ll see five specific points where the attack would have been stopped by controls that come bundled with security tools most small businesses already pay for.

Monday: how I picked you

I work regular hours and run a small volume operation. My spreadsheet has about 40 prospects per month, and I prefer businesses between 10 and 50 staff. The reason for that range is economics. Large enterprises have security teams, incident response contracts, and lawyers who make recovery expensive on my end. At the other end of the scale, sole traders rarely have enough at stake to bother with. A 22-person commercial services company sits in the right zone: payroll, customer database, project files, supplier relationships, and an owner who will pay to get the lot back. The return per hour is better at this size than at either extreme.

I did not find you through a breach or a tip. I found you on a public business records portal. State business registries, federal contract awards, and county-level licensing databases publish enough detail for me to identify your company, look up your name, estimate your revenue, and pick the most useful person inside the business. One search told me your company name, your registered agent, the contract value of a recent municipal job, and the named contact on the submission.

The fact that nothing has gone wrong at your company yet is the strongest signal I get. It tells me your credentials are probably still valid, your staff has not been trained to spot anything, and nobody has had a reason to change a password. A clean record is the first indicator I look for.

Tuesday: building your org chart for free

I spend about 40 minutes researching your company today using only a browser.

LinkedIn gives me eight of your current employees with their job titles listed. Your office manager has been there for six years and lists “accounts payable, payroll, and supplier invoicing” in her profile summary. Your second admin joined 14 months ago. You list yourself as director, with a sparse profile and a low connection count, which tells me you are unlikely to notice when someone unusual starts engaging with your profile or your company’s social media.

Public business filings confirm your registered business name and your full legal name. A “meet the team” post from two years ago on your Facebook page lists first names and photos, including someone described as helping out in the office a couple of days a week. One of the commenters shares your surname.

I now know who handles your money, what their name is, how long they have been there, what software they probably use (I will check your job ads on Indeed for the phrase “experience with QuickBooks or Sage”), and who in your business has the authority to approve a payment without a second signature.

That last person is my primary target. You are harder to reach and probably more cautious. Your office manager has system access, handles supplier payments, and is busy enough that one more email in her inbox does not get scrutinized the way it might if she had nothing else to do.

I have not spent a dollar yet.

Wednesday: I bought your credentials for $14

Stealer logs are credential packages harvested by infostealer malware that infected someone’s personal device, often months or years earlier. The malware records every username and password typed into the machine, then bundles the data for sale. Marketplaces on Telegram channels and forums let buyers search these logs by company email domain.

I search for your company’s email domain. Two results come back. One is your office manager’s work email, with a password that looks like it was saved in her browser. The other is a personal Gmail address that appears to belong to a family member of yours, probably from a device that shared a home network.

I pay $14 for the package. It takes four minutes.

Your office manager’s password follows a common pattern: a pet or child’s name combined with a year and an exclamation mark. I check it against HaveIBeenPwned, which is the same free database security professionals use, and find that it appeared in a credential dump from a retail loyalty program breach three years earlier. The password has not been changed since.

Your family member’s credentials are more interesting than they look at first. The same password, with minor variations, shows up across a streaming service, a gaming account, and your company’s Microsoft 365 login. The password works. The only thing standing between me and the inbox is the second factor.

Total spend so far: $14.

Thursday: getting past your MFA

Multi-factor authentication stops a lot of attacks, but the implementation matters more than the checkbox.

Simple push-notification fatigue does not work against your office manager’s account. Microsoft enabled number matching by default for all Microsoft Authenticator push notifications in May 2023, which means she would have to type a code from her login screen rather than just tap approve. Push bombing fails against that configuration.

What still works is adversary-in-the-middle (AiTM) phishing. I send your office manager an email designed to look like a routine Microsoft 365 password reset notification, citing the breach that her password appeared in (the same breach I found her credentials in earlier in the week). The link in the email takes her to a page that mirrors the real Microsoft sign-in screen. That page is a proxy I control.

When she enters her password and approves her MFA prompt, my proxy forwards both to the real Microsoft login server. Microsoft validates the credentials, completes the MFA challenge, and issues a session token back to my proxy. I capture the token. She sees a normal login experience on what she thinks is the real Microsoft site, then a “password updated successfully” message.

I am now signed in as her. The MFA prompt succeeded, and the session token sits in my browser instead of hers. Microsoft sees a valid authenticated session and treats my activity as legitimate.

I had a backup plan in case the email did not get clicked. Earlier in the day, I called your office posing as your IT support company, using a name I found in a Google review you had left 18 months earlier. I told your receptionist that we were seeing unusual login activity on the office manager’s account and that I would need her to approve a verification push in the next few minutes. She said the office manager was not at her desk. I said no problem, I would try again later. The call cost me nothing.

By Thursday night, I am inside your office manager’s Microsoft 365 account. I set up an inbox forwarding rule so her emails copy to an address I control without notifying her, then I wait.

Friday 2:47pm: why I waited 36 hours before encrypting

I spend 36 hours reading email before I encrypt anything. That dwell time is how I size the ransom correctly.

In those 36 hours, I find your cyber insurance policy attached to an email from your broker, with a cyber liability sub-limit of $250,000. A bank reconciliation your office manager sent you two weeks ago shows your business account at around $180,000 at month end. Your customer list sits in a quote template she emailed to herself, and a message thread with a municipal project manager mentions a job starting in three weeks with a hard deadline you cannot afford to miss.

I set my ransom at $65,000 in cryptocurrency. That figure is low enough that you will pay rather than fight it, high enough that it is worth my time, and well within what I know you can access. Ransoms set above 10 percent of visible liquid assets tend to get contested. The figure I picked sits below that line.

I deploy the encryption payload at 2:47pm on Friday. The timing is deliberate. Your bookkeeper finishes at 3pm on Fridays, which I know from an out-of-office reply I saw in the forwarded emails. You are on a job site, with your calendar synced to the shared inbox. The person most likely to notice something wrong and call for help is already gone, and the person with the authority to make decisions is unreachable.

By the time anyone understands what has happened, it is a Friday evening, every file on your shared drive is encrypted, and a ransom note sits on every screen in your office.

Total cost to me: $14 for credentials and about six hours of work spread across the week.

Five places this attack would have died

The attack on your business worked because five ordinary things were not in place. None of them were expensive. Most were already bundled into security tools you already pay for.

1. The credential purchase on Wednesday.

HaveIBeenPwned is free. Microsoft Entra password protection can detect and block reused or commonly-compromised passwords across your accounts. Enforcing unique passwords per account, through a password manager and through Entra’s policies, makes a stolen credential purchase useless for me.

2. The MFA bypass on Thursday night.

Microsoft already blocks the simpler push-bombing attack, because number matching has been enabled by default for all Microsoft Authenticator push notifications since May 2023. The current dominant credential-based bypass is adversary-in-the-middle phishing. Defenses include phishing-resistant MFA (FIDO2 hardware keys, passkeys, or Windows Hello for Business), Conditional Access policies that require a compliant or hybrid-joined device, and anti-phishing protection in Microsoft Defender for Office 365. Any one of these would have either prevented the session token capture or made the captured token unusable from my IP address.

3. The inbox forwarding rule.

Microsoft 365 allows admins to block external email forwarding rules at the tenant level. With that block in place, the inbox forwarding rule I used to read 36 hours of email would not have worked. I might have encrypted anyway, but I would have been guessing on the ransom size.

4. The 36-hour dwell time.

Microsoft Defender for Business, included in Microsoft 365 Business Premium, generates an alert when a new inbox forwarding rule is created. If anyone had been watching those alerts, or if the alerts had been routed somewhere visible, I would have been detected on Thursday night. The most impactful change for a business your size is rarely a new product purchase. The improvement comes from someone reviewing the security alerts that the tools you already pay for are already generating.

5. The public business records.

You cannot unpublish a state contracting registry or a federal contract award. That data will stay public. What you can control is what your team chooses to post about their specific responsibilities. Your office manager’s LinkedIn profile listed her financial responsibilities in enough detail to make her the obvious target. That detail is worth a conversation with your team, framed as practical security awareness rather than a rule about what people can post.

Three questions to send your IT provider

These three questions cover most of where the example attack failed. Each one corresponds to a control that comes bundled with security tools you most likely already pay for.

1. Are we using phishing-resistant MFA (FIDO2 keys, passkeys, or Windows Hello for Business) for finance, admin, and executive logins?
2. Is external email forwarding blocked at the tenant level?
3. Are our security alerts going somewhere, and is someone reviewing them?

Frequently asked questions

Do hackers target small businesses?

Yes. Most ransomware operations target small and mid-sized businesses because the ratio of payout potential to defensive resources is higher than at either extreme of company size. The volume sweet spot is roughly 10 to 50 staff, where there are assets worth encrypting but no dedicated security team to defend them.

What is adversary-in-the-middle (AiTM) phishing?

AiTM phishing is a technique where the attacker hosts a proxy page that mirrors a real login screen, such as Microsoft 365 or Google Workspace. When the user enters credentials and approves the MFA prompt, the proxy captures the resulting session token. The legitimate service treats the login as successful, but the session token ends up in the attacker’s browser. AiTM has become the dominant credential-based attack vector against Microsoft 365 tenants after the default rollout of number matching ended simpler push-bombing attacks.

What is a stealer log?

A stealer log is a package of credentials harvested by infostealer malware from an infected personal device. The logs include browser-saved passwords, session cookies, and stored authentication tokens, and they are sold on underground markets for $10 to $20 per package. The malware that creates them typically infects personal computers through pirated software or malicious browser extensions.

How much does it cost an attacker to compromise a small business?

In the example walkthrough above, the total spend was $14 for stolen credentials and about six hours of work. Costs vary, but the threshold to attempt the kind of attack described in this post sits well below $100.

Are there free tools that would have stopped this attack?

Several of the controls referenced in the walkthrough come bundled with Microsoft 365 Business Premium licenses that businesses in this size range typically already hold. External forwarding restrictions and Defender for Business alerts are configuration changes rather than new purchases. HaveIBeenPwned is a free check available to anyone. Phishing-resistant MFA hardware keys are a small per-user cost compared with the cost of a successful ransomware incident.

Sources and further reading

• CISA: Stop Ransomware Guide — federal guidance on the controls referenced throughout this walkthrough.
• Microsoft Learn: How number matching works in MFA push notifications — Microsoft’s documentation on the default-enabled Authenticator feature that blocks push-bombing attacks.
• HaveIBeenPwned — the free database used to check whether an email address has appeared in known breaches.
• Microsoft Learn: Configure external email forwarding in Microsoft 365 — how to block tenant-level external forwarding rules.

If any of this walkthrough sounded uncomfortably similar to your environment, the three questions above are a good starting point. Your IT provider should be able to confirm what is in place and what is not within an hour or two. And if you don’t have an IT provider, feel free to reach out to us and we’ll help you sort it.

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This Article has been Republished with Permission from The Technology Press.

Most cyberattacks do not start with a sophisticated intrusion. They start with a click on a personal email, a reused password, or a file uploaded to a familiar cloud service because the approved option felt slower.

The Verizon Data Breach Investigations Report found that 68% of breaches involve the human element. 

Not a zero-day exploit. Not a brute-force attack on a hardened system. Human behavior, in the course of an ordinary working day.

For businesses running cloud-based workflows across multiple devices, the personal and professional overlap is now the rule. Understanding where that overlap creates risk is no longer optional. It is a core part of modern security strategy.

The Risk Sitting Outside Your Security Stack

Personal web habits are not reckless behavior. They are normal behavior.

Checking a personal inbox on a work laptop. Logging into a social account during a break. Saving a work password in a browser already loaded with personal accounts. Uploading a document to a storage service because it is faster than the approved option.

None of these feel like security decisions in the moment. But each creates a connection between personal digital activity and business systems, and that connection sits outside most traditional security controls.

Hardening systems, deploying tools, and locking down networks addresses part of the problem. The rest moves with the people.

How Personal Web Habits Create Business Exposure

Personal channels are phishing’s preferred territory

Personal inboxes, messaging platforms, and social media feeds are where phishing thrives. 

These environments are harder to filter, easier to spoof, and loaded with the emotional triggers that make people act before they think.

When those channels share a device or browser with business systems, a single click can cross the boundary instantly.

Phishing is the most common entry method for attackers precisely because it exploits distraction rather than technical weakness. The target does not need to be careless. They just need to be busy.

Password reuse turns personal breaches into work incidents

Password reuse is one of the most direct connections between personal and professional exposure. 

When credentials from a personal account are compromised, attackers run them against business systems automatically. This technique, credential stuffing, is low-effort and highly effective because so many people use the same password across multiple accounts.

Unique credentials for every account, combined with multi-factor authentication, break that chain. 

A personal breach has nowhere to go when the work account requires a second factor that the attacker cannot relay.

Shadow IT is usually about convenience, not defiance

Most unauthorized tool usage does not begin with disregard for IT policy. It begins with a productivity gap. Employees use personal cloud storage, consumer messaging apps, or AI tools because they are faster and more familiar than the approved alternative.

The security risk is not the intention behind the choice. It is what happens to the data. 

Once business information moves into platforms that IT cannot see, audit, or secure, it falls outside every control in place. The tool usage is predictable. The data exposure is not.

Why Blocking Behavior Doesn’t Work

The instinct is to lock things down: block personal apps, restrict browsing, enforce strict device policies.

In practice, blanket restrictions rarely stop the behavior. They relocate it. Users find workarounds. Unapproved tools move to personal devices. IT teams lose visibility into exactly the activity they were trying to manage. 

The risk does not disappear. It moves somewhere harder to see.

Security strategies that assume perfect compliance perform poorly in real workplaces. The goal is not eliminating the overlap between personal and professional digital activity. It is managing it without breaking how people work.

What Actually Reduces Risk

The controls that work are the ones that match how people actually operate.

Separate contexts, not people

The simplest way to reduce crossover risk is to reduce crossover. 

Separate browser profiles for work and personal activity, clear guidance on where business accounts should be accessed, and identity boundaries that prevent accidental mixing all reduce exposure without restricting what people do with their time.

This is not about surveillance. It is about creating enough distance between personal and professional digital activity that a compromise in one does not automatically reach the other.

Design for credential failure

Assume passwords will eventually be exposed somewhere. Design for that outcome rather than hoping to prevent it.

CISA reports that enabling multi-factor authentication makes accounts 99% less likely to be compromised, even when the underlying password has already been stolen.

MFA converts the most common attack path into a dead end. 

Stolen credentials from a personal breach cannot reach a work account that requires a second factor. A password manager handles unique credentials across every account, making that protection sustainable without placing an unrealistic burden on users.

Make secure behavior easier than unsafe behavior

Personal web habits are not dangerous by default. Ignoring the risk they create is. The most secure environments today are not the most restrictive. They are the most realistic: built around how people actually work, designed to contain failure when it happens, and focused on making safer behavior the path of least resistance.

Helping clients reduce human-driven security risk is one of the most impactful services an MSP can offer. 

Contact us or schedule a consultation to review current controls and identify where the most important gaps are.

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This Article has been Republished with Permission from The Technology Press.

It’s a statistic that sends a shiver down the backs of SME owners, managers and employees.  

According to the FBI’s 2025 Internet Crime Report, business email compromise (BEC) cost US businesses more than $3 billion last year.

This makes it one of the most financially damaging cybercrimes on record. 

AI has made these attacks harder to detect. The question for AP teams is no longer whether they can identify suspicious requests. It is whether the processes around payments make fraud difficult regardless of how convincing it looks.

Why AP Teams Are in the Crosshairs

Accounts payable sits at the intersection of trust and timing. AP teams process invoices, manage supplier details, and execute payments, often under pressure to keep operations running smoothly. 

For attackers, that combination is ideal.

Most successful fraud does not involve breaking into systems. 

The FBI’s Internet Crime Complaint Center (IC3)  has consistently found that BEC attacks rely on impersonation. This involves posing as a trusted executive, supplier, or internal colleague to redirect payments or update bank details before anyone notices.

AI has made that impersonation dramatically more scalable. 

Where it once required skill and time to craft a convincing request, tools are now widely available that automate the research, writing, and contextual tailoring that make fraud blend into normal AP workflows.

By mid-2024, an estimated 40% of BEC phishing emails were already AI-generated, with that share expected to grow significantly.

What AI-Enhanced Fraud Looks Like in Practice

Emails that blend into normal workflow

Traditional phishing relied on volume and imperfection. AI has changed that. 

Modern BEC emails are grammatically correct and written in the specific tone of the executive or supplier being impersonated. They reference active projects, current invoice numbers, and upcoming payment runs. 

For AP teams processing high volumes of routine communications, that level of familiarity is exactly what lowers the guard.

Invoice and payment redirection

One of the most common AP fraud patterns involves payment redirection. 

Attackers may intercept a legitimate invoice exchange and quietly alter the destination account. They then send a short message claiming a supplier has updated its banking details, or re-issue a real invoice with minor modifications. 

The surrounding content looks entirely legitimate because, in many cases, it is drawn from real correspondence. 

Voice cloning and executive impersonation

Email isn’t the only channel being exploited. 

AI voice-cloning tools can replicate a person’s voice from a short audio sample. That makes it possible to leave convincing voicemails or place calls that sound like a known executive.

For AP teams accustomed to verbal approvals on high-value or urgent payments, this removes one of the few remaining verification methods that email security alone cannot address. 

Why Traditional Checks No Longer Work

Security awareness training still matters, and investing in it remains worthwhile. But AI has changed what AP teams are up against.

 Attacks no longer contain the signals that training programs once focused on: awkward phrasing, mismatched logos, odd sender addresses, or generic greetings. 

Modern fraud emails can reference the recipient’s organization, active suppliers, and current invoice values drawn from publicly available or previously intercepted sources.

When a fraudulent request is indistinguishable from a legitimate one, placing the burden of detection on the AP team puts it in the wrong place. 

The organizations that reduce risk are not asking staff to be more suspicious. They are building verification processes that work independent of how a message looks.

Building Process Around the Risk

The most effective defense is not sharper instincts. It is removing ambiguity from high-risk actions.

Out-of-band verification as standard

Any request to change supplier bank details or approve an urgent payment outside the normal cycle should require secondary confirmation through a known, independent channel — not a reply to the same email thread. Calling a supplier on a number already on file, or confirming with a colleague directly, breaks the impersonation chain regardless of how convincing the original request appeared. This step does not require technology. It requires a written procedure and the team’s habit of following it.

Layered access and authentication controls

Restricting access to financial systems and enforcing multi-factor authentication limits the damage a compromised account can cause. If an attacker gains access to a vendor’s email, MFA requirements on the receiving end create friction that can slow or stop a fraudulent change before any money moves.

A culture that supports slowing down

Fraud prevention improves when staff feel safe questioning requests, including from senior leadership. 

A team member who pauses a payment to verify it is not being obstructive. They are doing exactly what good process requires. 

Building that culture starts with leadership modeling the behavior and making clear that slowing down on high-risk actions is always the right call.

The FBI’s 2025 Internet Crime Report included a dedicated AI section for the first time, logging more than $893 million in AI-enabled scam losses across more than 22,000 complaints.

When verification is standard and questioning is encouraged, AI-enhanced fraud loses much of its advantage. 

The technology attackers use is advancing quickly, but the process controls that contain the damage do not have to be complicated. They have to be consistent.

Shift the Burden From People to Process

Concerned about AI-enhanced fraud targeting your finance teams or clients? 

Contact us or schedule a consultation to review your current controls and identify where the most important gaps are.

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This Article has been Republished with Permission from The Technology Press.

You click a link, sign in, approve the MFA prompt, and get on with your day. Completely unaware that someone else just logged into your account at the same moment.

That scenario surprises many businesses, particularly those that rely on multi-factor authentication (MFA) to protect cloud accounts. But this is exactly how Adversary-in-the-Middle (AiTM) phishing attacks work. 

Rather than stealing passwords for later use, these attacks silently hijack an already-authenticated session in real time.

MFA remains a core control, and getting it implemented correctly is still a critical first step for any business. 

But AiTM attacks exploit something MFA was never designed to protect: the trusted session that exists after authentication has already completed.

Phishing Has Moved Beyond Passwords

Phishing remains the most common starting point for account compromise, but the objective has changed. 

Traditional phishing collected usernames and passwords. Modern phishing is after something more immediately useful: the authenticated session itself.

Security researchers have documented a significant shift toward session and token theft, where attackers intercept the authentication process as it happens. 

Rather than reusing stolen credentials, which MFA typically blocks, they wait until the user successfully completes login, then steal the session token that proves it already occurred.

The technique has matured quickly. Phishing-as-a-Service (PhaaS) platforms now supply ready-made proxy toolkits that let even low-skilled attackers run AiTM campaigns targeting Microsoft 365 and Google Workspace. 

How AiTM Attacks Actually Work

The fake login page that isn’t fake

An AiTM phishing site is not a basic replica of a login page. It is a live reverse proxy.

The attacker’s infrastructure sits between the user and the real authentication service. Every keystroke, redirect, and server response flows through the attacker’s system in real time. From the user’s perspective, nothing looks wrong. 

The page behaves exactly like the real service, with correct branding, working redirects, and a functioning MFA prompt. In most cases, the only clue is a slightly altered URL that goes unnoticed on a mobile screen or when someone is under time pressure.

Why MFA doesn’t stop it

This is where many security assumptions fall apart.

MFA protects the moment of authentication, not what comes after it. 

Once a user successfully completes MFA, the service issues a session cookie. What this means is that the cookie signals to the application that the user is already verified. From that point, no password or MFA prompt is required. The system trusts the token. Whoever holds the cookie holds the access.

AiTM attacks simply wait for that cookie to be issued then steal it.

Microsoft tracked a 146% rise in AiTM attacks over the past year, as cybercriminals increasingly shift focus to accounts already protected by MFA.

Much of this increase is driven by PhaaS platforms like Evilginx that allow even low-skilled attackers to run convincing reverse-proxy campaigns at scale, targeting major cloud identity providers with minimal setup.

Session cookies

Session tokens act as bearer credentials. So, whoever possesses the token can access the account, with no password or MFA challenge required.

Once the cookie is stolen, the attacker imports it into their own browser and immediately resumes the session. 

This is a session replay attack. The attacker does not log in. They pick up where the legitimate user left off, inside a fully trusted, already-verified session.

What Happens After a Session Is Stolen

The aftermath of an AiTM attack tends to be quiet, which is precisely what makes it dangerous. 

The attacker is operating inside a legitimate, authenticated session. There are no failed MFA attempts, no unusual login alerts, and nothing in standard sign-in logs to signal a problem.

Research from Proofpoint shows that attackers who gain access through session hijacking commonly create hidden inbox rules to redirect mail, register additional MFA methods to lock in persistent access, monitor email threads for financial conversations, and use the trusted account to launch phishing campaigns against internal colleagues or finance teams.

These follow-on actions are a key reason AiTM attacks are frequently uncovered late, after financial fraud, data exposure, or wider network compromise has already begun.

Reducing Your Exposure

MFA is still essential. Building strong authentication practices remains the starting baseline. But reducing AiTM risk requires controls that extend beyond the login event itself.

Adopt phishing-resistant MFA

Methods like FIDO2 hardware keys and passkeys bind authentication to the specific device and the legitimate domain. A proxy in the middle cannot relay them: the process fails if the URL is not the real one. 

The Canadian Centre for Cyber Security analyzed over 100 AiTM campaigns targeting Microsoft Entra ID accounts. It found that phishing-resistant MFA consistently blocked session theft where standard MFA methods (including push notifications and one-time passcodes) did not.

Tighten Conditional Access policies

Risk-based access controls evaluate additional signals, including device compliance, IP location, and session behavior, rather than treating every authenticated session as permanently trusted. 

Configured correctly, these policies can detect and block anomalous access even when a stolen session token appears valid.

Monitor for post-login anomalies

Detecting AiTM compromise typically means watching for activity after login: new MFA method registrations, inbox rules created outside business hours, access from unfamiliar locations, or unusual data activity. 

Authentication logs alone will not surface the problem.

Train users on URL awareness

Employees who understand that a working MFA prompt on an unfamiliar-looking page still represents a risk are better positioned to pause, check the URL, and report before a session is compromised. A brief team walkthrough of what AiTM lures look like in Microsoft 365 contexts can meaningfully reduce exposure.

Stop Protecting Just the Login Screen

MFA is a baseline, not a finish line. The businesses that reduce AiTM risk are the ones that understand how sessions, tokens, and identity trust actually work . And they build controls around each layer, not just the login screen.

Want to review your identity security controls? 

Contact us or schedule a consultation to identify the gaps that matter most before an incident does it for you.

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This Article has been Republished with Permission from The Technology Press.

MFA is a strong front-door lock. But it’s not the only thing that decides whether someone can get in.

After you sign in, your browser keeps you logged in using a session token (often stored as a cookie). It’s the digital version of a wristband at an event: once you’ve been checked, the wristband proves you belong there. If an attacker steals that wristband, they may not need to beat your MFA prompt at all.

That’s the core of session cookie hijacking. The attacker isn’t “cracking” MFA. They’re skipping it by replaying your already authenticated session.

This isn’t a reason to stop using MFA. It’s a reason to stop treating MFA as the finish line. 

When sessions can be stolen, the practical defence shifts to layered controls: phishing-resistant sign-ins, device hygiene, tighter session policies, and detection that catches suspicious access early.

Why MFA Isn’t a “Game Over” Control

MFA is still one of the best upgrades most businesses can make, but it doesn’t end an attack on its own. The reason is that attackers don’t always try to beat the login step. They try to go around it.

Cloudflare notes that “attackers are finding new ways to circumvent MFA” and that modern incidents are rarely one isolated technique. They’re “part of a chain of attacks.” 

In other words, MFA can block a lot of credential theft, but it doesn’t automatically protect what happens after a user successfully signs in. 

That’s where session cookie hijacking comes in. 

Microsoft has described adversary-in-the-middle phishing campaigns where attackers use a reverse-proxy site to “steal and intercept” a user’s password and the session cookie that proves they have an authenticated session. 

This is “not a vulnerability in MFA.” The attacker isn’t breaking the MFA. They’re reusing the session. 

What a Session Cookie Is and Why Attackers Want It

When you sign into a web app, the site needs a way to remember that you’ve already proved who you are. That’s what a session is: a temporary “logged-in” state that saves you from entering your password and MFA code on every click. 

Kaspersky explains that session hijacking is “sometimes called cookie hijacking” because cookies are commonly used to store the session identifier that keeps you authenticated. 

Attackers want that session identifier because it’s the shortcut. 

Proofpoint describes session tokens as digital “keys” that let a user stay authenticated. It warns that stealing valid tokens lets attackers impersonate legitimate users and potentially bypass authentication measures “like MFA.” 

That’s why session cookie hijacking is so highly leveraged. 

If an attacker can steal the cookie or token that represents your active session, they’re not trying to defeat the login process. They’re attempting to reuse what you already completed, and access the same apps and data as if they were sitting at your keyboard.

How Session Cookie Hijacking Actually Happens

A lot of teams picture “account takeover” as someone guessing a password or tricking a user into approving an MFA prompt. 

Session cookie hijacking is different. The attacker’s goal is to steal the proof that you’re already logged in, then reuse it, often without triggering another sign-in challenge.

1.) AiTM phishing 

Adversary-in-the-middle (AiTM) phishing is the “proxy login” trap. 

You think you’re signing into a normal service, but you’re actually signing into a lookalike page that sits between you and the real site. The attacker relays the login in real time, so everything appears to work, including MFA.

Attackers use AiTM phishing sites to “steal and intercept” a user’s password and the session cookie that proves the authenticated session. This is “not a vulnerability in MFA.” The attacker isn’t breaking the MFA. They’re capturing the session after MFA is completed and reusing it. 

One such campaign “attempted to target more than 10,000 organisations” since September 2021, which shows how scalable this approach has become. 

2.) Browser-in-the-Middle session stealing

Browser-in-the-middle (BitM) is similar in spirit, but it’s even more “hands-on” from the attacker’s side. 

Instead of stealing a password and running away, the attacker effectively places themselves in control of the browsing session.

Google’s threat intelligence says, “Stealing this session token is the equivalent of stealing the authenticated session.” Once the token is stolen, “an adversary would no longer need to perform the MFA challenge.” 

In other words, the attacker isn’t trying to authenticate instead of you. They’re trying to ride along after you’ve authenticated.

3.) Cookie theft from the endpoint

Not every session hijack starts with a fancy proxy. Sometimes the attacker simply steals session data from the device itself.

Stealing valid session tokens allows attackers to impersonate legitimate users. Tokens act like digital “keys.” If an endpoint is compromised, those “keys” can be extracted and reused.

Invicti explains that an attacker steals HTTP cookies and can gain access. The goal is often to obtain sensitive information stored in cookies. 

MFA Is a Baseline, Not a Finish Line

MFA is still essential. It blocks a huge amount of credential theft and makes basic account takeover harder. But session cookie hijacking is a reminder that attackers don’t always try to defeat the login step. Sometimes they reuse what happens after it.

The practical response is layered and realistic. Make phishing harder to pull off, and treat device health as part of identity. Tighten session behaviour for high-risk apps. Watch for suspicious access patterns that suggest a session is being replayed.

When those controls work together, MFA stops being a comforting checkbox and becomes what it should be: a strong baseline that’s backed by protections around the session itself.

Contact us today for help protecting your login sessions from hijacking.

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This Article has been Republished with Permission from The Technology Press.