Let's face it: most security training is forgettable. We've all encountered stale slides, outdated videos, and quizzes that are more of a formality than a genuine learning experience. But every October we get a chance to turn the tables with Security Awareness Month.
If you're looking to elevate the culture of security at work, this is the perfect time to create true change. Don't think in terms of lectures and compliance checklists. Think of developing habits. Instincts. Awareness that sticks.
Why Security Awareness Month Needs Your Attention
Cybersecurity Awareness Month is more than another program. It's a powerful chance to reboot your company's security mindset.
Why? Because the majority of breaches don't occur because you’re being targeted by a nation-state-level threat. They happen because someone clicked on a malicious link, reused a poor password, or didn't see through a social engineering ploy. Human error is the #1 cause of successful attacks.
That is why October is important. Done right, it’s the ideal time to break through the distractions and create good habits across the organization.
If you approach this month as a checkbox to complete, you'll get checkbox outcomes. But if you approach from a mindset of culture change — something playful, regular, and constructed with real people in mind — you'll have greater engagement, better decision-making, and reduced incidents. Remember, this is not about scaring your employees. It is about empowering them.
When done right, Security Awareness Month becomes a springboard for year-round vigilance. And it shows your team (and leadership) that security isn’t just IT’s job, it’s everyone’s responsibility.
Looking for some inspiration? Try these 10 clever, useful, and even playful ways to make Security Awareness Month matter.
10 Easy (and Cheap) Ideas for Security Awareness Month
1. Build a "Security Myth-Busting" Campaign
Start the month by debunking some common security myths. Produce a series of short emails, Slack or Teams posts, or posters to display at the office. Here are some examples:
- Hackers do not target small companies — False
- Strong passwords equal safety — Not necessarily
- Antivirus software is enough to keep me safe — It helps, but it’s not a silver bullet.
Keep it short. Keep it jargon-free. And add a few good stories to make people remember.
2. Conduct a Phishing Simulation, With a Gamified Twist
We all think we know how to identify a phishing email, until we don't.
Yes, there is a lot of simulated phishing, but during October, why not try to make it a game?
Send fake phishing emails weekly (or even daily) during the month. Award points for proper identification and reporting. Create a leaderboard. Have small rewards. Adding some friendly competition is how people remain attentive and actually learn.
Pro tip: Don't shame people who click. Turn it into a learning opportunity, not a "gotcha" moment.
3. Create a "Security Snack" Series
Nobody wants to sit through a 90-minute webinar.
Instead, have short, bite-sized learning sessions during lunch or afternoon breaks. 10–15 minutes at the most.
Topics may include:
- Ways to identify phishing attempts
- Securing personal devices
- Social engineering techniques
- Safe surfing practices
Make it fun. Bring snacks (or send your remote workers a $5 gift card for a free coffee). Call it “Security & Snacks.” People show up for snacks.
Consider adding some of Anagram’s interactive modules to make it interesting. Not cartoons. Not fluff. Short, real-world puzzles that require critical thinking.
4. Set up a "Wall of Red Flags"
Construct a (real or virtual) “wall” of cyber threats your employees are actually seeing. Work with your SOC or even ask your own employees to contribute real instances of suspicious emails, suspicious-looking links, or unusual tech activity they've dealt with. Explain why those were red flags.
It’s a living, breathing, crowd-sourced awareness instrument, unique to your company, and a wonderful way for employees to learn from one another.
5. Turn Your Developers Into Security Champions
Security isn’t justan IT or compliance issue, it's everyone's responsibility. But what about your developers? Well, they are at the forefront.
Use Cybersecurity Awareness Month to upskill your engineering team with Anagram Security’s Developer Training. We teach developers using short puzzles that place them in the shoes of the attacker and lets them figure out how to exploit common vulnerabilities. Then we teach them how to fix them.
Ditch the sterile textbook problems. Give them real bugs to hunt downIt helps them create more robust code, and teaches threat modeling from the inside out.
Less theory. More "aha" moments.
6. Host a Cybersecurity Escape Room
Yep, it’s a thing. There are physical and virtual cyber-themed escape rooms. Players in teams cooperate to unravel mysteries, reveal clues, and "escape" a threat.
It is experiential, collaborative, and surprisingly effective at conveying key ideas. Much more memorable than a slide deck.
7. Create a "Secure Habits" Checklist (and a Giveaway)
For most companies, their awareness training is merely a once-per-year reminder. Help employees create secure habits that last by using a basic checklist:
- Set your screen to automatically lock after 60 seconds of inactivity
- Download your company’s official password manager
- Report a suspicious email to the security team
- Make sure all your computer software is up-to-date
Tie it to a giveaway: everyone who completes the checklist (and sends you evidence) is entered into a raffle.
Anagram Security can help with this. By customizing our modules to incorporate your policies and documentation, we help make habits second nature.
8. Share "Breach of the Week" experiences
Nothing is as attention-grabbing as a real disaster.
Share a short write-up of a recent security breach every week. Bonus points if it comes from a company that’s relevant to your industry. Focus on what went wrong and how it could’ve been prevented. Keep it short and tight. You can include takeaways that readers can implement today.
It is not fear-mongering, it's motivation.
9. Reward Reporters
Develop a culture where employees feel encouraged to speak. During Security Awareness Month, acknowledge team members who:
- Report phishing attempts
- Flag shady software
- Provide security suggestions
- Help teammates stay safe
Public shout-outs. Digital badges. Small rewards. It helps people become more confident and realize that security is everyone's responsibility. Once your employees start feeling a sense of ownership, that’s when things start to shift.
10. Gather Feedback and End with a Security Q&A
Close the month with an open, judgment-free question and answer session. Invite your security team, or someone from the Anagram Security team (yes, we do this a lot!), to answer questions in real time. Create a safe space where employees can ask things like:
- What’s the difference between malware and ransomware?
- Why is reusing passwords a bad idea?
- Why can’t I use ChatGPT at work?
Keep it simple. Keep it helpful. Make people leave more knowledgeable than when they arrived.
And once you’re done with awareness month, ask your employees what they thought. What worked? What didn’t? What do they still want to know?
Making the Issue Stick Past October
October's vibe is wonderful, but what about November?
The greatest companies make Cybersecurity Awareness Month a starting point, not an endpoint (see what we did there?). Creating a secure company culture isn’t achieved with a few sessions of workshops and emails. It’s about changing behavior: a process that requires consistency.
Here’s the truth: most people forget what they learned two weeks after training. That’s why you need tools and programs that reinforce lessons over time.
Behavior nudges. Short, interactive content. Critical thinking. Training that answers the question “why do I care?”. That’s the secret to success.
At Anagram Security, we build our product to instill instinct, not just knowledge. Not one-and-dones, but bite-sized modules that enable people to create security reflexes they bring to work every day naturally.
Yes, so go big in October. Run simulations. Host events. Get people talking. But also establish a plan for the next steps. Select tools that put security front-of-mind throughout the year. Monitor engagement and make changes based on what works.
Awareness is not a campaign. It's a way of life. And the companies that understand this don't only sidestep breaches, but create trust and actual competitive advantage.
Two Trainings Worth Exploring
If you're serious about pushing your security culture to the next level, look at Anagram Security’s two flagship solutions:
1. Security Awareness Training
No tedious videos. No patronizing quizzes. Just short, interactive, real-life scenarios that create muscle memory, not simply knowledge. In Anagram’s general Security Awareness Training, users are presented with threats, they solve puzzles, and they receive immediate feedback. It's only a few minutes per module, but the lessons last for years.
2. Developer Security Training
Teach your engineers to think like attackers, so they can code like defenders. We highlight real-world OWASP vulnerabilities in real applications in Anagram Security’s Developer Training. Your devs won’t just memorize best practices, they’ll live them. Equip them with tools that actually work. And make security something that matters to them, not something they just tick off.
Why Companies Choose Anagram Security
Let's be honest: security training usually sucks. It's too dry, too elementary, and too tedious. It's no wonder most employees immediately forget the lesson the minute the session is over. Anagram Security turns the script around. Our modules are designed to be enjoyed. Yes, really. They're short and sweet, with interactive puzzles that put the user in real-world situations. People think. React. Solve. And they remember.
No lengthy videos. No cartoon characters. No silly quizzes. Simply rapid, effective challenges to complete over a coffee break. It's centered on the science of learning and one simple notion: treat people like grown-ups.
For developers, we're more than theory from a textbook. We let developers practice with real code, real bugs, and real attacks. Engineers learn to identify and remediate vulnerabilities as they actually show up in real applications, not in some kind of sanitized simulation.
Companies choose Anagram Security because it’s effective. It respects users' intelligence and time. And it’s designed for companies who don’t want to merely "tick the box," but genuinely mitigate risk.
If you're looking for training that alters behavior, not just statistics, then Anagram Security is for you.
Getting Ready to Make This October Count
If you want this year's Cybersecurity Awareness Month to do more than check a box, these 10 ideas are a good start. From myth-busting campaigns to interactive puzzles, each idea, executed well, is crafted to engage, educate, and make a real difference.
Need help bringing it all to life? Anagram Security has got your back with bite-sized, brain-stimulating lessons that people actually enjoy and learn from.
Whether you need to level up your whole organization or just your developers. Anagram Security provides the tools to do so in no time.
Join us in creating a security culture that endures throughout the entire year, not just in October.
