
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
Free 15-minute callNo obligationPersonal reply within 1 business day

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.
Book My 15-Minute Fit CallFree 15-minute call · No obligation
Your next best step
Service
Cybersecurity services
Small business cybersecurity services: a risk review of access, email, devices and backups, then MFA, EDR and tested backups. Request a…
Free tool
Cyber risk quiz
Free small business cyber risk assessment: answer 5 questions on remote access, backups, phishing, updates and IT management to see your risk profile.
Read next
How do I keep my business safe from hackers?
How to protect your small business from hackers: EDR that stops attacks, backups that can't be deleted, and staff training.
Talk to us
Book a 15-minute fit call
Tell us what's leaking time or revenue. You get a personal reply within 1 business day.

- Founder-led. Built by Jared Casper (Founder) and Mark Casper (Co-Founder).
- A person answers. Every request gets a personal reply within 1 business day. Call or text 1-207-222-7737.
- Done for you. We build, set up and run the system — see exactly what we do.
