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 5

Needs Space

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

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.

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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.

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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.

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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.

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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.

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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

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Day 7

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Day 8

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Day 9

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Day 10

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Day 21

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Day 22

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Day 24

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Day 26

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Day 27

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Day 28

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Day 29

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Day 30

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Day 31

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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.

Book a free check-in

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.