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Why SMBs Are the #1 Cybercrime Target in 2026

By  Tony Fairclough  ·  3 minute read

Cybercriminals have finally figured something out: it’s easier (and often more profitable) to break into ten small businesses than one well-defended enterprise. And in 2026, that trend will only intensify. If you’re responsible for IT at an SMB in Ontario, you’ve seen the shift firsthand; more phishing attempts, more alerts, more credential misuse, more suspicious Microsoft 365 activity.

And yes, attackers are targeting you on purpose.

This isn’t fearmongering. It’s the reality the data keeps reinforcing: SMBs are now the #1 target in Canada for cybercrime, and attackers are doubling down.

Let’s break down the “why”, and more importantly, what you can do about it.

Why Cybercriminals Prefer SMBs Over Enterprises

Attackers aren’t stupid. They go where the defenses are weakest, and where the payout is predictable. For SMBs, three things paint a target on your back:

1. Limited IT Resources

Most Ontario SMBs operate with:

  • A single IT manager or small team

  • No full-time security staff

  • Shared responsibilities spread thin

  • A backlog of patches and configuration tweaks

  • Dependency on Microsoft 365 but little hardening

Attackers know this. They exploit it.

2. Valuable Data, Minimal Defenses

Small businesses handle:

  • Customer information

  • Financial records

  • HR files

  • Internal business documents... yet few have enterprise-grade visibility or real-time detection.

The value is there. The defenses usually aren’t.

3. High Likelihood of Paying Ransom

SMBs can’t afford multi-day downtime. Attackers know a small business will often pay faster than a large one.

A one-day outage can cost thousands. A multi-day outage can cripple a business.

The Attack Patterns Hitting Ontario SMBs Right Now

From our work with small businesses across Ontario, the patterns are consistent.

Pattern #1: Credential Theft & Microsoft 365 Intrusions

Attackers target:

  • Weak MFA enforcement

  • Misconfigured Entra ID permissions

  • Over-permissive service accounts

  • Legacy authentication still enabled

Once they’re in, they stay quiet, often for weeks.

Pattern #2: Endpoint Exploits on Laptops

With hybrid teams, SMB devices:

  • Move between home and office

  • Connect to unsecured Wi-Fi

  • Skip patches for weeks

Attackers slip in through:

  • Unpatched vulnerabilities

  • Malicious email attachments

  • USB device misuse

Pattern #3: Malware/Ransomware via Phishing

SMB staff click more often than they think. Not because they’re careless, but because modern phishing is convincing.

Pattern #4: Dark Web Credential Reuse

Credentials from one breached website get sold, reused, and matched against your corporate accounts.

If the password is reused, attackers walk right in.

This is why dark web monitoring is no longer a “nice to have.”

What Makes SMBs “Easy Wins” for Cybercriminals?

Attackers see SMBs as low-effort, high-reward opportunities. Their playbook hasn’t changed much, but the volume and automation sure have.

Attackers exploit typical SMB gaps:

  • Lack of 24/7 monitoring

  • Infrequent patching

  • Limited security awareness training

  • Inconsistent backups

  • No vulnerability management program

  • No dedicated security policies

They know you’re juggling operations, budgets, vendors, and fires; and they exploit that chaos.

What Ontario SMB IT Leaders Can Do Starting Now

Here’s the practical part. The steps that actually move the needle.

1. Harden Microsoft 365 Immediately

At minimum:

  • Enforce MFA everywhere

  • Disable legacy authentication

  • Review admin role assignments

  • Enable mailbox audit logging

  • Require strong password policies

This is the #1 entry point right now.

2. Deploy EDR on Every Device

Traditional antivirus isn’t enough.

EDR gives you:

  • Behavioral detection

  • Isolation capabilities

  • Real-time alerting

  • Threat correlation

If your laptop gets compromised, you need the ability to isolate it instantly.

3. Implement Continuous Vulnerability Management

Not quarterly. Not yearly. Continuous.

This includes:

  • Automated scanning

  • Risk scoring

  • Patch prioritization

  • Reporting that you can share with leadership

Vulnerabilities are how attackers get in silently.

4. Train Your People (But Keep It Short)

Short, monthly micro-trainings outperform long annual sessions.

Focus on:

  • Phishing identification

  • MFA hygiene

  • Password practices

  • Email safety

Your people are your front line.

5. Test Your Backups, Don’t Just Trust Them

The biggest disaster in a breach? A backup that appears to exist but doesn’t actually restore.

Test:

  • Recovery speed

  • Integrity

  • Offsite availability

If you can’t restore fast, you don’t have a backup, you have a placeholder.

How Contego Helps SMBs Close These Gaps

Contego’s SMB Services were built specifically for this reality; small IT teams, limited budgets, rising threats.

Bronze Plan (Foundational Protection)

  • Dark web monitoring

  • Website scans

  • Automated backups

  • EDR + AV

Silver Plan (Scaling SMB Security)

Everything in Bronze, plus:

  • Security Awareness Training

  • 24/7 Incident Management

  • Managed SOC

Gold Plan (Mature Security Posture)

Everything above, plus:

  • vCISO guidance

  • Policy development

  • Governance support

  • Full IT security roadmap

This is enterprise-grade security, sized for SMBs.

Attackers Are Coming. SMBs Must Be Ready.

Whether your team has one IT person or a small crew, the reality is the same: you’re being targeted more than ever before. Cybercriminals don’t care about your size, only your vulnerability. But with the right protections, SMBs can be incredibly resilient.

If you want clearer visibility, stronger protection, and a security stack that’s built for the realities of small business, book a consultation with Contego.

We’ll walk you through your risk exposure and build a plan that fits your size, your systems, and your budget.