Avoid These Common Cybersecurity Mistakes Chicagoland Businesses Make

Cybersecurity mistakes aren’t always the result of sophisticated hackers—most breaches happen because businesses overlook fundamental security practices that seem too basic to matter. 

74% of breaches involve the human element, whether through error, manipulation, or misuse, according to the IBM Cost of a Data Breach Report. Even more concerning, third-party involvement in breaches has increased significantly, creating a concerning threat landscape for businesses globally. 

46% of all cyber breaches impact businesses with fewer than 1,000 employees, making SMBs prime targets, according to research from StrongDM. 

For Chicago businesses, recognizing these common cybersecurity mistakes is the first step toward building stronger defenses. Here are the most frequent cybersecurity mistakes Chicagoland SMBs make and practical guidance to help you avoid them. 

Underestimating the Human Element in Cybersecurity 

The problem: Human error remains the leading cause of data breaches, according to the IBM Cost of a Data Breach Report, yet many Chicagoland businesses still treat employee security training as a one-time checkbox exercise. 

Employees of small businesses experience 350% more social engineering attacks than those at larger enterprises, according to StrongDM. Daily threats include: 

• Phishing emails that appear legitimate 

• Pretexting calls designed to extract information 

• Credential theft attempts targeting weak passwords 

• Social engineering exploiting human psychology 

One annual training session cannot prepare employees for evolving threats. Cybercriminals constantly refine their tactics, using AI-generated phishing emails that are nearly indistinguishable from legitimate messages, as noted in Hoxhunt’s report. 

The solution: Organizations that invest in comprehensive cybersecurity services with continuous employee training see measurably better results. When your team understands the risks and knows how to respond, they become your strongest line of defense rather than your weakest link. 

Delaying Software Updates and Patch Management 

Vulnerability exploitation has surged as an initial attack vector in the past year, according to CISA’s Known Exploited Vulnerabilities Catalog. Despite this alarming trend, only 54% of perimeter-device vulnerabilities were fully remediated by organizations, with a median fix time of 32 days, according to Statista. 

Those 32 days represent a wide-open door for attackers. 

Many Chicago SMBs lack dedicated IT support to monitor and apply patches consistently. The consequences include: 

• Exploited vulnerabilities providing easy entry points for attackers 

• Increased ransomware risk from known security gaps 

• Compliance failures that result in fines and penalties 

• System instability from accumulated security debt 

Without proactive IT support, patch management becomes reactive—addressing problems only after they cause damage. Businesses that rely on managed IT services benefit from automated patch management that keeps systems current without disrupting daily operations. 

Overlooking Third-Party and Vendor Risks 

Third-party involvement in breaches has increased significantly, according to CISA’s Known Exploited Vulnerabilities Catalog. 

Your security is only as strong as your weakest vendor. A breach at a software provider, payment processor, or logistics partner can expose your data even when your own systems are secure. 

Common vendor security gaps: 

• No security documentation or unclear standards 

• Inadequate access controls 

• Missing incident response procedures 

• Lack of regular security assessments 

Chicago businesses should require security documentation from all vendors handling sensitive data. Organizations working with virtual CIO services gain strategic guidance on vendor risk management and can implement structured evaluation processes that many businesses lack the internal IT support to manage effectively. 

Using Weak Passwords and Skipping Multi-Factor Authentication 

80% of data breaches involve compromised credentials, according to Expert Insights. Even more striking: 61% of breaches involved unauthorized credentials, according to Expert Insights. 

Despite these statistics, password security remains one of the most commonly overlooked areas in Chicagoland SMBs. Employees reuse passwords across multiple platforms, choose easily guessable combinations, or store credentials in unsecured locations. 

Multi-factor authentication (MFA) blocks over 99% of automated attacks, yet many businesses still haven’t enabled it across all systems. 

Essential password security practices: 

• Unique passwords for every business account 

• Password managers to generate and store complex credentials 

• Multi-factor authentication on all business-critical systems 

• Regular password rotation for high-privilege accounts 

Professional IT support services can configure MFA across your organization and set up password management tools that make security easier for your team. Businesses that partner with managed IT providers gain consistent security to prevent cybersecurity mistakes, and oversight without hiring additional staff. 

Neglecting Backup and Disaster Recovery Planning 

10% of breaches analyzed in recent reports involved ransomware. SMBs bear the brunt of these attacks—85% of ransomware attacks target small and medium businesses. 

The stark reality: 75% of SMBs could not continue operating if hit with ransomware. 

Many organizations back up data but never test whether they can actually restore it, according to Veeam’s Ransomware Trends Report. Storage failures, configuration errors, or incomplete backups only become apparent during an emergency—when it’s too late. 

The 3-2-1 backup rule: 

• Three copies of your data 

• On two different media types 

• With one copy stored offsite 

Recovery procedures should be documented, tested quarterly, and accessible to multiple team members. Businesses that implement disaster recovery planning with reliable IT support establish tested protocols that protect operations during worst-case scenarios. 

Strengthening Your Security Posture 

Avoiding these common cybersecurity missteps doesn’t require enterprise-level budgets or large IT teams. It requires awareness, consistent practices, and the right IT support to ensure your defenses stay current. 

Each of these vulnerabilities is preventable with structured planning, ongoing attention, and access to reliable managed IT services. 

At LeadingIT, we help Chicagoland businesses build practical cybersecurity strategies through comprehensive managed IT services that address these vulnerabilities. Our team provides ongoing IT support, employee training, and proactive monitoring to keep Chicago SMBs protected from cybersecurity mistakes without overwhelming internal resources. 

Ready to strengthen your security posture? Schedule a free cybersecurity assessment to identify gaps in your current defenses and learn how we can help protect your business.