How Phishing Bypasses Basic Security (And Why SMBs Are Still Getting Burned)

Most small and mid-sized businesses think they’re “covered.” 

They have antivirus software.

They have spam filtering.

They might even have MFA turned on.

And yet… phishing emails still get through. Accounts still get compromised. Money still gets lost.If you’ve ever wondered why this keeps happening, this post will explain it in simple terms and, more importantly, show what SMBs can actually do about it.

The Big Misconception: “We Have Security, So We’re Safe”

Basic security tools were designed for known threats. Phishing today is anything but known. Modern phishing attacks are:

• Personalized
• Context-aware
• Often sent from real, previously compromised accounts
• Designed to trick humans, not machines (Group, 2026)

Attackers no longer try to break your security. Instead, they find ways to get around it.

How Phishing Actually Bypasses Basic Security

Let’s break down the most common ways phishing slips past “standard” protections.

1. Legitimate Accounts Are the New Malware

Traditional email security looks for:

• Suspicious domains
• Known bad IPs
• Malware attachments

But attackers now:

• Compromise a real Microsoft 365 or Google Workspace account
• Send emails from a trusted domain
• Reply to existing email threads (Hackers are stealing Microsoft 365 accounts by abusing link-wrapping services, 2025)

To your security tools, this looks completely normal. To your staff, it looks even more trustworthy.

2. MFA Doesn’t Stop Phishing by Itself

MFA is important, but it isn’t a complete solution. Common MFA bypass techniques include:

• MFA fatigue attacks (push notifications until someone clicks “Approve”)
• Session token theft via fake login pages
• Man-in-the-middle phishing kits that capture credentials and MFA in real time (Multi-Factor Authentication & Smishing, n.d.)

Result?

The attacker logs in as the user, with MFA satisfied. No alerts. No lockouts. No antivirus warning.

3. Links Aren’t “Malicious” (Yet)

Many phishing emails use:

• Legitimate file-sharing services
• URL shorteners
• Newly registered domains (Group, n.d.)

At the time of delivery:

• The link has no bad reputation
• The site hasn’t been flagged
• There’s no malware present

Often, by the time the link is flagged as malicious, the harm has already happened.

4. Humans Are the Final Gate (And the Weakest One) (Kaseya: SMBs remain cautious on AI despite persistent human error threat, 2025)

Basic security assumes users will:

• Spot fake invoices
• Question password reset emails
• Recognize subtle impersonation

In reality:

• People are busy
• Phishing emails look urgent and familiar
• Attackers copy real branding, signatures, and writing style

Just one distracted click can cause a problem.

5. No One Is Watching for “Suspicious but Valid” Behavior

Most SMB environments lack:

• Sign-in risk monitoring
• Impossible travel detection
• Conditional access enforcement
• Automated account response

So when an attacker logs in:

• From a new country
• At an unusual time
• Accessing SharePoint, OneDrive, and email rules

Nothing happens. This happens because, technically, the login was considered “successful.”

Why SMBs Feel the Pain More Than Enterprises

Enterprises assume breaches will happen.

SMBs assume prevention is enough. That difference is expensive. SMBs often experience:

• Wire fraud and invoice redirection
• Business email compromise (BEC)
• Ransomware launched after phishing
• Long recovery times with no visibility into what happened (Business Email Compromise — FBI, 2024)

And the worst part? Many don’t realize they were phished until weeks later. (2024 Data Breach Investigations Report, n.d.)

What Actually Stops Modern Phishing

Stopping phishing today requires layers, not checkboxes. At a minimum, SMBs should be looking at:

• Strong conditional access policies (not just MFA)
• Phishing-resistant authentication where possible
• Email authentication (SPF, DKIM, DMARC)
• User sign-in risk detection and automated response
• Ongoing user awareness that reflects real attacks, not generic training

Security should assume credentials may be stolen and focus on limiting the damage that results.

Final Thought

Phishing isn’t winning because SMBs are careless. 

It’s winning because attackers evolved faster than basic security setups. (Bradley, 2025)If your defenses were set up 5 to 10 years ago, they are probably being bypassed today, often quietly and efficiently, without any obvious warning signs.The question isn’t if phishing will reach your users.

It’s about whether your environment can detect and contain it before it becomes a business problem.

Written by Jaspreet Singh — Microsoft identity & security practitioner. Author at ITBlogs.ca. Lab notes and testing at f11.ca.

References

Group, A. W. (January 3, 2026). APWG Q3 Report: Phishers Target Victims in New, Intrusive and Menacing Ways. APWG Q3 Report. https://apwg.org/apwg-q3-report-phishers-target-victims-in-new-intrusive-and-menacing-ways

(July 31, 2025). Hackers are stealing Microsoft 365 accounts by abusing link-wrapping services. TechRadar. https://www.techradar.com/pro/security/hackers-are-stealing-microsoft-365-accounts-by-abusing-link-wrapping-services

(n.d.). Multi-Factor Authentication & Smishing. https://www.hhs.gov/sites/default/files/multi-factor-authentication-smishing.pdf

Group, A. W. (n.d.). Global Phishing Survey 2H2014: Trends and Domain Name Use. https://docs.apwg.org/reports/APWG_Global_Phishing_Report_2H_2014.pdf

(November 10, 2025). Kaseya: SMBs remain cautious on AI despite persistent human error threat. ITPro. https://www.itpro.com/business/business-strategy/kaseya-smbs-remain-cautious-on-ai-despite-persistent-human-error-threat

(December 31, 2023). Business Email Compromise — FBI. FBI. https://www.fbi.gov/how-we-can-help-you/scams-and-safety/common-frauds-and-scams/business-email-compromise

Bradley, T. (March 5, 2025). Cyber Threats Are Evolving Faster Than Defenses. Forbes. https://www.forbes.com/sites/tonybradley/2025/03/06/cyber-threats-are-evolving-faster-than-defenses/

(n.d.). 2024 Data Breach Investigations Report. https://www.sifma.org/wp-content/uploads/2025/04/2024-dbir-data-breach-investigations-report.pdf