Cyber Awareness Dad Jokes ’26

Cyber Awareness Dad Jokes '26

31 days. 31 groan-worthy jokes. 31 lessons that keep a small business out of trouble.

A new one every morning at 8 AM Eastern, all October long, from Ron Trotto at TC³.

Latest: Day 24

Wrapped Up

Why did the mummy's server get hacked? It was all wrapped up in legacy software.

Software past its end of support never gets another security fix. Know which systems are out of support and put a date on replacing each one.

Day 1 · Phishing

Inbox Fishing

What's a hacker's favorite fishing spot? Your inbox. No license, no boat, and the fish click on their own.

The lesson

One click on a fake login page can hand over the keys to your whole email system. Train your team to stop and verify any message that pushes urgency, money, or a password reset.

Day 2 · Passwords and passkeys

Fluffy Knows

Why did Ron switch to passkeys? Because 'Fluffy2019' wasn't fooling anybody. Not even Fluffy.

The lesson

Pet names and birthdays are the first guesses attackers try, and reused passwords turn one leak into ten. A password manager or passkeys closes that door for every account at once.

Day 3 · MFA fatigue

Yes Man

What do you call an employee who approves every login request on their phone? A yes-man-in-the-middle.

The lesson

Attackers with a stolen password spam approval prompts until someone taps yes just to make it stop. Use number matching, and teach staff that a prompt they didn't start means call IT, not approve.

Day 4 · Patching

Remind Me Tomorrow

Why did the laptop go to the doctor? It had a chronic case of 'remind me tomorrow.'

The lesson

Many attacks walk through holes that already have a fix waiting. Set updates to install automatically and check monthly that they actually did.

Day 5 · Backups (3-2-1)

Needs Space

Why did the backup break up with the server? It needed space. Three copies of space, actually.

The lesson

Keep three copies of your data, on two kinds of storage, with one offline or offsite. Then test a restore, because a backup nobody has restored is just a hopeful guess.

Day 6 · Found USB drives

Parking Lot Prize

What did the USB stick in the parking lot say? 'Plug me in, I'm harmless.' Famous last words.

The lesson

Dropped drives are an old trick because curiosity still works. If you find one, hand it to IT unopened, and never plug an unknown device into a work computer.

Day 7 · Phone pretexting

Help Yourself Desk

The 'IT guy' on the phone said he was from the help desk. Turns out he was from the help-yourself desk.

The lesson

Real IT support will never ask for your password or an MFA code. Hang up and call back on a number you already know.

Day 8 · Deepfake voice fraud

Boss Voice

Why don't deepfake bosses ever call twice? Because the moment you call back on the real number, they lose their voice.

The lesson

Cloned voices are good enough to fool a bookkeeper in a hurry. Any request to move money or share credentials gets verified on a known number, no matter how familiar the voice sounds.

Day 9 · Shadow AI data leaks

Makeover Mistake

Why did the client spreadsheet feel so exposed? Somebody pasted it into a free chatbot to make it prettier.

The lesson

Free AI tools may keep what you paste in, including client names and financials. Give your team an approved AI tool and a simple rule about what never goes into the others.

Day 10 · AI hallucinations

Tall Tales

Why would a chatbot make a great fisherman? It tells stories about the one that got away with total confidence.

The lesson

AI writes fiction in the same calm tone it writes fact. Check every number, name, and citation before it goes to a client, because they'll hold you to it, not the bot.

Day 11 · AI agent permissions

Time Out

Why did the AI assistant get sent to time out? It had access to everything and asked permission for nothing.

The lesson

An AI tool connected to email, files, and payments can do real damage with one bad instruction. Give it the least access that gets the job done, and keep a human on anything that spends money.

Day 12 · QR code phishing

Friendly Meter

Why was the QR code on the parking meter so friendly? It really wanted to meet your credit card.

The lesson

Scammers stick fake QR codes over real ones on meters, menus, and invoices. Type the address yourself or use the official app when money is involved.

Day 13 · Invoice and bank-change fraud

New Bank Who

My vendor emailed to say they changed banks. I said funny, you also changed how you spell your own name.

The lesson

One changed account number on a real-looking invoice can send a month of payments straight to a scammer. Confirm any change to payment details by calling a number you already have on file.

Day 14 · Cyber insurance proof

Prove It

Why did the insurance adjuster bring a magnifying glass? To find the MFA you swore you had.

The lesson

Insurers now ask for proof of controls like MFA and backups, and a wrong answer on the application can sink a claim. Make sure what you told them matches what is actually turned on.

Day 15 · Offboarding

Still Logged In

Why does the guy who quit last spring still come to every meeting? Nobody turned off his account, so technically he never left.

The lesson

Former staff with live logins are an open door, whether they mean harm or not. Build a same-day offboarding checklist for email, apps, shared files, and door codes.

Day 16 · Printers and smart devices

Leaky Printer

Why was the office printer brought in for questioning? It had a long history of leaking documents.

The lesson

Printers, cameras, and smart TVs sit on your network with default passwords and old software. Change the defaults, update them, and keep them off the network your accounting lives on.

Day 17 · Vendor and supply chain risk

Catering Entrance

Why do hackers love your vendors? It's easier to walk in through the caterer's door.

The lesson

Your data is only as safe as the vendors who can reach it. Ask your key vendors how they protect access to your systems, and cut off the ones who can't answer.

Day 18 · Incident response plan

Where to Panic

Why did the company tape its incident response plan to the break room fridge? So everyone would know exactly where to panic.

The lesson

A plan you have never practiced turns into a group text at 2 a.m. Write down who calls whom, keep a copy off the network, and walk through it once a year.

Day 19 · Laptop encryption

Taxi Trouble

Why wasn't Ron worried when he left his laptop in a taxi? It was encrypted. The only thing he lost was his dignity.

The lesson

A lost laptop without encryption can turn into a reportable data breach. With full disk encryption turned on, it's just an expensive inconvenience.

Day 20 · Written policies

We Just Know

Why did the auditor ask for the security policy in writing? Because 'we just kind of know' isn't a document.

The lesson

Clients, insurers, and auditors ask for written policies, not good intentions. A short, honest set of written rules wins deals and speeds up every questionnaire.

Day 21 · Mobile device security

Lost and Found

What's the difference between a lost phone with a screen lock and one without? About three business days of damage control.

The lesson

Phones hold email, MFA apps, and client texts. Require a screen lock and remote wipe on every device that touches company data.

Day 22 · Stale accounts

Zombie Accounts

Why are zombie accounts so dangerous? They never log off, and they're always hungry for data.

The lesson

Old accounts for former staff, test logins, and forgotten services are easy targets because nobody watches them. Review every account quarterly and delete what nobody owns.

Day 23 · Shadow IT

Ghost Apps

What do you call software nobody in IT knows about? A ghost app. You can't see it, but it can definitely see you.

The lesson

Every app someone signs up for with a work email is another place your data lives. Keep a list of approved apps and ask staff to check before they add one.

Day 24 · Legacy software

Wrapped Up

Why did the mummy's server get hacked? It was all wrapped up in legacy software.

The lesson

Software past its end of support never gets another security fix. Know which systems are out of support and put a date on replacing each one.

Day 25

Unlocks Oct 25

Day 26

Unlocks Oct 26

Day 27

Unlocks Oct 27

Day 28

Unlocks Oct 28

Day 29

Unlocks Oct 29

Day 30

Unlocks Oct 30

Day 31

Unlocks Oct 31

The jokes are free. So is a 15-minute cyber check-in.

If one of these landed a little too close to home, let's talk. You get a straight answer about where your business stands, and no sales pitch.

About these videos: Ron's likeness and voice are AI-generated, with his permission. The jokes and the advice are human-written and human-approved.