Don’t let overlooked obligations become incidents. Learn how.
Utility navigation bar redirect icon
Portal LoginSupportContact
Search
Close search
Huntress Logo in Teal
  • Platform Overview
    Managed EDR

    Get full endpoint visibility, detection, and response.

    Managed EDR

    Get full endpoint visibility, detection, and response.

    Managed ITDR

    Protect your Microsoft 365 identities and email environments.

    Managed ITDR

    Protect your Microsoft 365 identities and email environments.

    Managed SIEM

    Managed threat response and robust compliance support at a predictable price.

    Managed SIEM

    Managed threat response and robust compliance support at a predictable price.

    Managed Security Awareness Training

    Empower your teams with science-backed security awareness training.

    Managed Security Awareness Training

    Empower your teams with science-backed security awareness training.

    Managed ISPM

    Continuous Microsoft 365 and identity hardening, managed and enforced by Huntress experts.

    Managed ISPM

    Continuous Microsoft 365 and identity hardening, managed and enforced by Huntress experts.

    Managed ESPM

    Proactively secure endpoints against attacks.

    Managed ESPM

    Proactively secure endpoints against attacks.

    Integrations
    Integrations
    Support Documentation
    Support Documentation
    See Huntress in Action

    Quickly deploy and manage real-time protection for endpoints, email, and employees - all from a single dashboard.

    Huntress Cybersecurity
    See Huntress in Action

    Quickly deploy and manage real-time protection for endpoints, email, and employees - all from a single dashboard.

    Huntress Cybersecurity
  • Threats We Stop
    Phishing
    Phishing
    Business Email Compromise
    Business Email Compromise
    Ransomware
    Ransomware
    Infostealers
    Infostealers
    View Allright arrowView Allright arrow
    Industries We Serve
    Education
    Education
    Financial Services
    Financial Services
    State and Local Government
    State and Local Government
    Healthcare
    Healthcare
    Law Firms
    Law Firms
    Manufacturing
    Manufacturing
    Utilities
    Utilities
    View Allright arrowView Allright arrow
    Tailored Solutions
    MSPs
    MSPs
    Resellers
    Resellers
    SMBs
    SMBs
    Compliance
    Compliance
    What Gets Overlooked Gets Exploited

    Most days, nothing happens. But one day, something will.

    Huntress Cybersecurity
    Cybercriminals Have Evolved

    Get the intel on today’s cybercriminal groups and learn how to protect yourself.

    Huntress Cybersecurity
  • Pricing
  • Community Series
    The Product Lab

    Shape the next big thing in cybersecurity together.

    The Product Lab

    Shape the next big thing in cybersecurity together.

    Fireside Chat

    Real people. Real perspectives. Better conversations.

    Fireside Chat

    Real people. Real perspectives. Better conversations.

    Tradecraft Tuesday

    No products, no pitches – just tradecraft.

    Tradecraft Tuesday

    No products, no pitches – just tradecraft.

    _declassified

    Exposing hidden truths in the world of cybersecurity.

    _declassified

    Exposing hidden truths in the world of cybersecurity.

    Resources
    Upcoming Events
    Upcoming Events
    Ebooks
    Ebooks
    On-Demand Webinars
    On-Demand Webinars
    Videos
    Videos
    Whitepapers
    Whitepapers
    Datasheets
    Datasheets
    Cybersecurity Education
    Cybersecurity 101
    Cybersecurity 101
    Cybersecurity Guides
    Cybersecurity Guides
    Threat Library
    Threat Library
    Real Tradecraft, Real Results
    Real Tradecraft, Real Results
    2026 Cyber Threat Report
    2026 Cyber Threat Report
    The Huntress Blog
    Huntress Lands on the Microsoft Marketplace
    Huntress Cybersecurity
    Huntress Lands on the Microsoft Marketplace
    Huntress Cybersecurity
    How Huntress & DEFCERT Are Streamlining CMMC Assessment Prep
    Huntress Cybersecurity
    How Huntress & DEFCERT Are Streamlining CMMC Assessment Prep
    Huntress Cybersecurity
    Live Hacking Into Microsoft 365 with Kyle Hanslovan
    Huntress Cybersecurity
    Live Hacking Into Microsoft 365 with Kyle Hanslovan
    Huntress Cybersecurity
  • Why Huntress

    Go beyond AI in the fight against today’s hackers with Huntress Managed EDR purpose-built for your needs

    Huntress Cybersecurity
    Why Huntress

    Go beyond AI in the fight against today’s hackers with Huntress Managed EDR purpose-built for your needs

    Huntress Cybersecurity
    The Huntress SOC

    24/7 Security Operations Center

    The Huntress SOC

    24/7 Security Operations Center

    Reviews

    Why businesses of all sizes trust Huntress to defend their assets

    Reviews

    Why businesses of all sizes trust Huntress to defend their assets

    Case Studies

    Learn directly from our partners how Huntress has helped them

    Case Studies

    Learn directly from our partners how Huntress has helped them

    Community

    Get in touch with the Huntress Community team

    Community

    Get in touch with the Huntress Community team

    Compare Huntress
    Bitdefender
    Bitdefender
    Blackpoint
    Blackpoint
    Breach Secure Now!
    Breach Secure Now!
    Crowdstrike
    Crowdstrike
    Datto
    Datto
    SentinelOne
    SentinelOne
    Sophos
    Sophos
    Compare Allright arrowCompare Allright arrow
  • HUNTRESS HUB

    Login to access top-notch marketing resources, tools, and training.

    Huntress Cybersecurity
    HUNTRESS HUB

    Login to access top-notch marketing resources, tools, and training.

    Huntress Cybersecurity
    Partners
    MSPs

    Join our partner community to deliver expert-led managed security.

    MSPs

    Join our partner community to deliver expert-led managed security.

    Resellers

    Partner program designed to grow your cybersecurity business.

    Resellers

    Partner program designed to grow your cybersecurity business.

    Tech Alliances

    Driving innovation through global technology Partnerships

    Tech Alliances

    Driving innovation through global technology Partnerships

    Microsoft Partnership

    A Level-Up for Your Business Security

    Microsoft Partnership

    A Level-Up for Your Business Security

  • Press Release
    Huntress Announces Collaboration with Microsoft to Strengthen Cybersecurity for Businesses of All Sizes
    Huntress Cybersecurity
    Press Release
    Huntress Announces Collaboration with Microsoft to Strengthen Cybersecurity for Businesses of All Sizes
    Huntress Cybersecurity
    Our Story

    We're on a mission to shatter the barriers to enterprise-level security.

    Our Story

    We're on a mission to shatter the barriers to enterprise-level security.

    Newsroom

    Explore press releases, news articles, media interviews and more.

    Newsroom

    Explore press releases, news articles, media interviews and more.

    Meet the Team

    Founded by former NSA Cyber Operators. Backed by security researchers.

    Meet the Team

    Founded by former NSA Cyber Operators. Backed by security researchers.

    Careers

    Ready to shake up the cybersecurity world? Join the hunt.

    Careers

    Ready to shake up the cybersecurity world? Join the hunt.

    Awards
    Awards
    Contact Us
    Contact Us
  • Portal Login
  • Support
  • Contact
  • Search
  • Get a Demo
  • Start for Free
Portal LoginSupportContact
Search
Close search
Get a Demo
Start for Free
HomeBlog
Teach Yourself to Phish: The Strategy Behind Phishing Simulations
Published:
December 19, 2023

Teach Yourself to Phish: The Strategy Behind Phishing Simulations

By:
Chris Henderson
Share icon
Glitch effectGlitch effectGlitch effect

Security awareness training is easy to think about as a passive item. You go buy a training platform or SCORM files for your LMS, assign the annual training, set it to nag your people to watch the video, and you’re done.

While that approach certainly will fulfill some of the compliance requirements to perform annual security awareness training, is it actually improving the security posture of your organization?

Humans are both our biggest cybersecurity risk and our best detection engine. While humans and their identities are the target for initial access on most modern breaches, they are also far more capable of detecting ‘weird’ stuff than security tools. The proper security awareness training program minimizes the risk posed by your employees while also improving their response times when they detect something is off. Spending the extra time to bolster the human detection capabilities is some of the best ROI you can achieve in the security space.

Humans are our best detection engine

At Huntress, we train our human detection capabilities in two ways:

First - Monthly security awareness training. Every month our staff receive new training to watch, using our very own Security Awareness Training product. This is to keep security front of mind and ensure a base level of security acumen across the workforce. We use these to reinforce good cyber hygiene while also educating our staff on the tactics used by adversaries. (Want us to manage those monthly trainings on your behalf? Check out our managed learning option)

Second - Monthly (or more frequent) phishing simulations. We do these frequently and celebrate individual failures. Tracking the organizational failure rates and adjusting the phishing lures you use accordingly builds resilience.

Why Phishing Simulations?

Social engineering is an attack on the psychological traits we have as humans: an innate desire to be helpful, trusting of strangers, and a fear of getting in trouble. Attackers leverage techniques of fear, intimidation, urgency, empathy, compensation, or authority in order to spike an adrenaline response to their message. Their goal is to spike your ‘fight or flight’ response so you don’t stop and logically think about an email.

Simulated phishing

Attackers take advantage of the psychological traits we have the same way they exploit vulnerabilities on a server. They find a vulnerable asset and exploit that vulnerability in order to gain initial access to a system.

Simulated phishing has the same desired outcome as vulnerability scanning your servers. We want to know where there are weaknesses so we can address them. Said differently, we are enumerating our human attack surface.

Phishing simulations have three goals:

1. Exposure therapy

By regularly using the same psychological exploits social engineers use, we lessen their impact and reduce the likelihood of an adrenaline response.

In order to increase organizational resilience, you should rotate the tactics used in your monthly simulations each campaign.

2. Identify your most vulnerable

Some of your users will be more susceptible to social engineering attacks either due to a heightened sense of trust or a lack of technical knowledge required to inspect an email for legitimacy.

A single failure is a learning opportunity in and of itself. Celebrate when someone fails and owns their failure; they are going to be far less likely to click next time. However, a series of failures is an indication the user needs individualized help. Spend your time training your repeat clickers, not the one-offs.

3. Measure your organizational reporting

Phishing attacks can be combated quickly, when alerted upon. We can revoke emails from inboxes, send awareness announcements, and more. But it all depends on how quickly a campaign is reported.

I treat a campaign that is reported before the first click as a massive organizational success, regardless of the click rates on the rest of the campaigns. If you find users are failing your test before the test is reported, it's time to remind the organization how to report suspicious content.

Real-Life Examples

At Huntress, we phish our employees every single month. These are our actual results since January.

You will notice there are a few months where we had spikes in the click rate. These spikes are what we are after. As our click rates decreased from the prior month, I increased the difficulty of the emails.

Looking at our click rates, there is an interesting trend I want to point out. After a month where a large percentage of employees clicked the lure, there was a sharp decline in the following months. This is why we want to get our employees to fail. By failing the test, they become more aware of their vulnerability and pay better attention—at least for a few months, according to this data.

Behind the Phish

For the sake of keeping this brief, I want to talk through my strategy for the first two months of the year.

In January, our phishing emails went out mid-week during regular business hours. This got ~2% of our employees to click the link in the email. I used a generic lure of the promise of payment for completing some easy task—a survey, a feedback call, or a Covid-19 stimulus. This was an excellent outcome. It showed our organization had a good baseline ability to detect phishing emails when the sender was not expected.

February needed a harder scenario and we needed to test a different tactic. The February campaign also went out mid-week, but this time, it spoofed our internal conferencing tools. ~4% of our employees clicked the link. Still under the 5% I aim for, our employees know to look at the sender of emails. We also did not see a single re-clicker; no one who failed in January failed in February. Awesome. We also had our employees dropping screenshots of the phishing email all over Slack; the organic dissemination of the threat was quick to de-fang the simulation.

Every month, I aim to vary the tactics I use. I do not want our employees to expect the same phishing email every month, as it drives complacency. So when planning your phishing campaigns, think like a hacker with inside information.

I want to end with a call for empathy toward your employees who do click.

When an employee fails a phishing test, they often react with either shame or anger. Many will send messages or call with explanations as to why they failed, or just send messages of “sorry.” Do not reprimand these failures. These are opportunities to discuss what they could have done differently in the future and remind them that we do these tests specifically to increase awareness.

Ready to phish your own team? Join our Neighborhood Watch program to get NFR licenses of Huntress, including Huntress Security Awareness Training.

Categories
Cybersecurity Education
Summarize this postClose Speech Bubble
ChatGPTClaudePerplexityGoogle AI

See Huntress in action.

Our platform combines a suite of powerful managed detection and response tools for endpoints and Microsoft 365 identities, science-backed security awareness training, and the expertise of our 24/7 Security Operations Center (SOC).
Book a Demo
Share
Facebook iconTwitter X iconLinkedin iconDownload icon
Glitch effect

You Might Also Like

  • A Beginner’s Guide to Phishing Simulation Training for Employees

    Learn the essentials of phishing simulation training with our beginner's guide. Protect your organization by simulating real phishing attacks.
  • Mistakes to Mastery: Get to Know Phishing Defense Coaching from Huntress SAT

    Get to know Phishing Defense Coaching, the latest addition to Huntress SAT. This personalized feature helps teach learners how phishing simulations tricked them so they can better identify potential threats.
  • Effortless Phishing Simulations Now Part of Huntress Managed Security Awareness Training

    Read about our newest addition to Huntress Managed SAT, Managed Phishing, offering you expert-backed, hassle-free simulated phishing campaigns.
  • Deceitful Tactics and Honest Mistakes: Remedying Human Error Amid the Rise of Social Engineering Across Healthcare

    Understand the impact of human error across healthcare, and discover how Huntress’ managed solutions can better defend your organization from social engineering scams.
  • How to Offend Your IT Team: A Guide for the Security Unaware

    Ready to drive your IT team crazy? See our top security blunders and learn practical tips to improve your cybersecurity habits.
  • Take Control: Locking Down Common Endpoint Vulnerabilities

    Learn how to lock down common endpoint vulnerabilities like weak passwords and unpatched software to secure your systems against threats like phishing and malware.
  • Which States Are Most at Risk for Cyberattacks on Government and Infrastructure?

    Cyberattacks on U.S. government and critical infrastructure surged in 2023, with over 420 million global attacks. Learn which states are most affected and discover how Huntress can help protect your organization
  • Don’t Get Schooled: How to Catch a Phish

    This blog explores phishing and smishing, diving into how to analyze text messages for their validity and legitimacy.

Sign Up for Huntress Updates

Get insider access to Huntress tradecraft, killer events, and the freshest blog updates.
Privacy • Terms
By submitting this form, you accept our Terms of Service & Privacy Policy
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.
Huntress Managed Security PlatformManaged EDRManaged EDR for macOSManaged EDR for LinuxManaged ITDRManaged SIEMManaged Security Awareness TrainingManaged ISPMManaged ESPMBook a Demo
PhishingComplianceBusiness Email CompromiseEducationFinanceHealthcareManufacturingState & Local Government
Managed Service ProvidersResellersIT & Security Teams24/7 SOCCase Studies
BlogResource CenterCybersecurity 101Upcoming EventsSupport Documentation
Our CompanyLeadershipNews & PressCareersContact Us
Huntress white logo

Protecting 215k+ customers like you with enterprise-grade protection.

Privacy PolicyCookie PolicyTerms of UseCookie Consent
Linkedin iconTwitter X iconYouTube iconInstagram icon
© 2025 Huntress All Rights Reserved.

Join the Hunt

Get insider access to Huntress tradecraft, killer events, and the freshest blog updates.

By submitting this form, you accept our Terms of Service & Privacy Policy