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Password security training for employees: try a cracking-time simulator, roll a passphrase, see what a password manager and two-step sign-in stop.

WorkshopyOfficial
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10 steps · 2 quizzes · about 55 minutes · open any step, or read it here
In this password security training you learn how attackers get into accounts and the few habits that keep them out: long passphrases, one password per account, a password manager and two-step sign-in. You try each idea with made-up passwords before it is explained.
Most break-ins don't need clever hacking. Breach reports such as Verizon's yearly Data Breach Investigations Report list stolen credentials, a user name and its password, among the most common ways attackers get in.
Try it: press Start guessing and watch which password falls first.
Interactive · Two passwords, one attacker — try it in the lesson
In this lesson you'll:
It takes about 55 minutes, with a quiz in the middle, a practice round and a final quiz.
Takeaway: a password that follows a pattern falls fast, however complex it looks.
Attackers rarely guess your password by thinking about you. They use four methods that work on thousands of people at once:
Try it: press each way in and watch where the password travels.
Interactive · Four ways a password is stolen — try it in the lesson
Notice that in the first two, the strength of the password doesn't matter at all: the attacker gets it whole. That is why the rest of this lesson is about more than strength.
Takeaway: a strong password stops guessing and cracking; a unique one stops reuse; a second step stops most of the rest.
When an attacker has a stolen list of scrambled passwords, they can try every combination. The number of combinations is the number of possible characters, multiplied by itself once for every character:
$$\text{combinations} = (\text{characters to choose from})^{\text{length}}$$
Adding symbols makes the first number bigger. Adding characters makes the power bigger, and powers grow much faster. Eight characters from the whole keyboard (95 choices) give about 6.6 quadrillion combinations. Fifteen lowercase letters give about 1.7 sextillion, roughly 250,000 times as many.
Speed matters too. A login page can slow guesses to a handful a second. A stolen list scrambled with a slow method (such as bcrypt) allows thousands a second. One scrambled with a fast method can be guessed tens to hundreds of billions of times a second on graphics cards. The block uses 100 billion as an illustration of that worst case.
Try it: set 8 characters with all four sets on and note the time. Then turn off everything but lowercase and slide the length up until the time is longer.
Interactive · Cracking-time simulator — try it in the lesson
What length of lowercase letters beats 8 characters of everything?
Takeaway: each extra character multiplies the work; 15 or more characters is a good target.
The simulator assumed every character was picked at random. People don't pick at random, and attackers know it. Their cracking tools don't start at aaaaaaaa: they start with lists of leaked passwords, dictionaries and names, then apply rules that copy what people do:
A password built that way is guessed in seconds, even at 12 or 14 characters.
Try it: pick each example, then type a few made-up passwords of your own. Never type a real password into a page like this one.
Interactive · Run the attacker's rules — try it in the lesson
Why did "correct horse battery staple" fall, even though it's four words?
Takeaway: a password is strong when it is long and has no pattern a person would follow.
A passphrase is several words picked at random, such as velvet orbit pepper glacier trumpet. It is long, so it's strong, and it is made of words, so it's easy to type and remember.
The words must be picked by chance, not chosen. The classic method, called Diceware, rolls five dice for each word and looks the roll up in a list of 7,776 words (6 × 6 × 6 × 6 × 6 = 7,776). Each word multiplies the combinations by 7,776:
| Words | Combinations | Time to try all at 100 billion a second |
|---|---|---|
| 3 | 470 billion | about 5 seconds |
| 4 | 3.7 quadrillion | about 10 hours |
| 5 | 28 quintillion | about 9 years |
| 6 | 221 sextillion | about 70,000 years |
Four words is fine for an account that also has a second sign-in step, because no one can guess online that fast. For a password that protects everything else, such as your password manager or your computer sign-in, use five or more. A password manager's generator can make passphrases for you.
Try it: roll a few passphrases, then change the number of words and watch the time.
Interactive · Roll a passphrase — try it in the lesson
Takeaway: five or more random words: long enough to be strong, easy enough to type.
Four questions on what you've seen so far.
Question 1. Which change makes a password hardest to crack?
Question 2. Why is Larkfield2026! a weak password at Larkfield?
Question 3. What makes a passphrase strong?
Question 4. Your password was in a site's breach. Why does that put your other accounts at risk?
A strong password protects you from guessing and cracking. It doesn't protect you when it leaks whole, from a breached site or a fake sign-in page. Then it opens every account that uses it.
You can't stop other sites from being breached. You can make sure that a password leaked from one of them opens nothing else: give every account its own password. Your work password, above all, should never be used anywhere else.
Try it: run the bot with Dana's same password everywhere. Then turn on the VPN's second step and run it again. Then turn off the shared password.
Interactive · One leaked password, four accounts — try it in the lesson
Takeaway: one account, one password: a leak then stays where it started.
No one can remember dozens of long, unique passwords. A password manager remembers them for you. It is an app, or part of your browser, that keeps your passwords in an encrypted vault, locked by one strong passphrase you do remember.
It does three things for you:
Try it: open pages A, B and C. On which ones does the manager offer to fill in Dana's password?
Interactive · What a password manager sees — try it in the lesson
When the manager doesn't offer to fill on a page that should be familiar, don't copy the password across by hand. Stop and read the address.
Use the password manager your company provides for work accounts, and follow its rules for what goes in it. Protect the manager itself with a passphrase of five or more random words and two-step sign-in.
Takeaway: remember one passphrase; let the manager make, keep and fill the rest.
Two-step sign-in (also called multi-factor authentication, or MFA) asks for something more than the password: a code, an approval on your phone, a security key or a passkey. A stolen password alone then gets the attacker nowhere.
Second steps are not all equal:
A passkey replaces the password altogether: your phone or computer keeps a secret key for each site and proves it holds it after you confirm with your fingerprint, face or screen PIN. There is nothing to type, so nothing to leak or reuse.
Try it: the attacker already has Dana's password. Pick each second step and see which attacks still get in.
Interactive · Which second step stops which attack — try it in the lesson
Whatever second step you use: never approve a request you didn't start, and never read a code out to anyone. Your IT team will never ask for it.
Takeaway: turn on a second step everywhere it's offered; use a passkey or a security key where you can.
Leaks happen to careful people too. What matters is the next hour. The rules are short:
Try it: decide each situation before you see the answer.
Interactive · What would you do? — try it in the lesson
Takeaway: change it from the real site, change it wherever you reused it, and tell IT.
Work out each answer, then check. Type numbers without commas or spaces. A hint costs nothing.
Six questions on the whole lesson.
Question 1. What is credential stuffing?
Question 2. Which of these is the strongest password?
Question 3. Your password manager doesn't offer to fill in your password on a page that looks like your company's sign-in. What should you do?
Question 4. Your phone shows a sign-in approval at 23:40, and you are not signing in. What do you do?
Question 5. Which second step still works when the attacker has built a perfect copy of your sign-in page?
Question 6. Which of these are good password habits? (pick all that apply)
Workshopy shares this lesson under CC BY 4.0. Anyone may use and change it, with credit to you. Anyone can learn it here, free. A copy in your workspace is yours to change and run live; your students never need an account.
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