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5 Cybersecurity Mistakes Small Businesses Make (And How to Fix Them)

December 15, 20255 min read

Most small business breaches are not sophisticated attacks. They are the result of basic gaps that take less than a day to close. Here are the five we see most often when we work with businesses in the Chicago area.

1. No Multi-Factor Authentication on Business Accounts

A stolen password is all it takes to access your email, your files, and your financial accounts. Multi-factor authentication adds a second step to the login process, so a leaked password alone is not enough to get in.

Turn on MFA for every account that touches client data or company finances. This includes Microsoft 365, Google Workspace, your banking portal, and your accounting software. It takes about thirty minutes to enable and stops the majority of account takeover attacks.

2. Shared Logins and Weak Passwords

Using the same password across multiple accounts, or sharing a single login among staff, is one of the most common ways small businesses get compromised. If one account is breached, attackers try the same credentials everywhere else.

A password manager like Bitwarden or 1Password costs less than five dollars per user per month. Every employee gets a unique, strong password for every account. Setup takes about an hour for a small team.

3. No Tested Backup Strategy

Ransomware works by encrypting your files and demanding payment to restore access. If you have a clean, tested backup from before the attack, you can restore without paying. If you do not, you are choosing between the ransom or losing your data.

Cloud sync tools like OneDrive and Google Drive are not backups. They sync in real time, which means a ransomware attack can encrypt the cloud copy too. You need a separate, automated backup with offsite or isolated storage, and you need to test that it actually restores.

4. Software That Is Not Being Updated

Every unpatched piece of software is a potential entry point. Attackers actively scan for systems running outdated versions of Windows, Office, browsers, and third-party applications.

Software updates should be scheduled and automatic, not left to individual employees clicking 'remind me later.' Patch management is not glamorous, but neglecting it is one of the most reliable ways to end up compromised.

5. Staff Who Have Not Had Security Training

Most breaches start with a phishing email. A staff member clicks a link, enters their credentials on a fake login page, and hands over access to an attacker. The attacker does not need any technical skill. They just need someone to click.

One hour of phishing awareness training per year makes a real difference. Walk your team through what a phishing email looks like, what to do if they receive one, and who to call if they accidentally click something. This does not require a formal program or a large budget.

None of these fixes require a large IT investment. They require attention and follow-through. If you are not sure where your business stands on any of these, we offer a free IT security assessment for businesses in the Chicagoland area. We will go through your setup and tell you honestly what needs to change.

ITM Consulting

Questions about your IT setup?

We work with small businesses and accounting firms across the Chicago area. Schedule a free 30-minute consultation and we will tell you honestly what we see.