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Phishing scams targeting small business

Phishing Scams Targeting Small Businesses: What to Look For

You can spot most phishing emails by five red flags: false urgency, a sender address that doesn't match the display name, unusual requests from "leadership," unexpected links or attachments, and generic greetings.

Updated · by Jared Casper

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Jared Casper

June 7, 2026

6 min read

The Evolution of Phishing

Today's phishing emails are highly targeted and grammatically perfect (thanks to AI).

They are designed to look like a vendor invoice, an urgent message from the boss, or a security alert from Microsoft.

Red Flags Your Team Must Know

1. The Urgent Request

Hackers create a false sense of urgency so you act before thinking: "Urgent: Wire Transfer Required" or "Your Account Will Be Suspended in 24 Hours."

2. The Mismatched Sender Address

The name might say "Microsoft Support," but if you click on the email address, it actually says support@micr0soft-security-update.com. Always verify the actual email address, not just the display name.

3. Unusual Requests from Leadership

A classic scam is an email pretending to be the CEO or owner, asking an employee to quickly buy gift cards for a "client presentation." Train your team to always verify unusual requests via phone or in person.

4. Suspicious Links and Attachments

Never click a link to log into an account. Go directly to the website yourself. Be extremely wary of unexpected PDF or ZIP attachments, especially invoices you weren't expecting.

5. Generic Greetings

While targeted attacks will use your name, many phishing emails still use generic greetings like "Dear Customer" or "Valued Employee."

Train Your Human Firewall

Technology can only block so much. Your employees are your last line of defense. Ask us about security awareness training, or take the Cyber Risk Quiz to see how exposed you are.

Frequently asked questions

What is the most common phishing scam against small businesses?

A classic one is an email pretending to be the owner or CEO asking an employee to quickly buy gift cards or wire money. Always verify unusual requests by phone or in person.

How do you spot a phishing email?

Look for five red flags: false urgency, a sender address that doesn't match the display name, unusual requests from leadership, unexpected links or attachments, and generic greetings.

How can I tell if an email sender address is fake?

Check the actual email address, not just the display name. A message labeled 'Microsoft Support' may really come from a lookalike domain with swapped characters.

How should staff verify an unusual payment or gift card request?

Confirm it by phone or in person with the person who supposedly sent it, never by replying to the email.

Is it safe to click a login link in an email?

No. Go directly to the website yourself and log in there instead of using the link.

Which email attachments are most likely to be phishing?

Unexpected PDF or ZIP files, especially invoices you weren't expecting. Be extremely wary of them.

Can phishing emails have perfect grammar now?

Yes. AI helps attackers write targeted, grammatically perfect emails, so look for urgency, mismatched senders and odd requests rather than typos.

Does security awareness training help stop phishing?

Yes. Technology can only block so much, and trained employees are your last line of defense. Ask CasperB2B about training or take the free Cyber Risk Quiz.

Before you book

Common concerns, answered

“We're too small to be a target.”

Small businesses get hit by the same phishing, ransomware and password attacks as big ones. Here's why size doesn't protect you.

“What will this cost me?”

You get a fixed, written quote before any work starts. Nothing begins until you've seen the full price and signed the scope. How pricing works.

“I don't have time to manage another project.”

You don't have to. It's done for you: we build, set up and run it. See exactly what we handle.

“Will I actually reach a person?”

Yes. Founder Jared Casper reviews every new request and you get a personal reply within 1 business day. Or call or text 1-207-222-7737.

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