I dislike several aspects of this quiz, and think it's actively harmful to users. It's great to train on the URLs, but that's not the only warning sign with these.

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1) "Hey there. Here is the doc you asked for."

Did you ask for a doc? Do you know this person? If no, these facts alone should be giant warning signs.

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2) Fax Message from efacks.com

Do you have an account with this service, where you explicitly signed up to receive faxes? If not, obviously you shouldn't be getting faxes from them so it's not legitimate.

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5) "Please find attached the 2019 financial activity report for your perusal."

Aside from giving away the answer in the title [1], this isn't a good example.

First line of defense, once again: Do you have an account with "Westmount Day School", and are you expecting a "financial activity report"?

Also, spoofing "from" e-mail addresses is a thing, and completely trivial, so relying on that is not a way to verify authenticity.

What's not mentioned is being aware of what PDF reader you're using: eg, do you regularly make sure it's up to date? Personally, I use Chrome as my PDF reader as I'm not a fan of Adobe products or their security track record in general.

Also in my experience, these types of e-mails often come in with an attachment like "2019 F.A.R.pdf.exe" (or a zip file that contains an exe), and not an actual PDF file. This would have been a great way to train users on this point.

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6) "Someone has your password"

The two reasons that this isn't legitimate are listed as "We don't use google.support to send emails" and "This link points to a subdomain of ml-security.org, not Google." [2]

So once again, spoofing "from" addresses is trivial -- so that is not a security measure. Secondly, how should I know what mail comes from? There was an earlier example of a legitimate message from Dropbox coming from a non-dropbox.com address (dropboxmail.com).

Also, the best defense against this is not mentioned: Never log into sites by clicking on links in e-mails! This includes changing your password. The only exception to this is a password reset mail when you explicitly just asked for a password reset.

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7) "Government-backed attackers may be trying to steal your password"

Once again, "Change password" link in e-mail. Don't click it.

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8) Tripit Security prompt [3]

Sorry, but this is a terrible example.

First of all, am I trying to perform some action with Tripit that this prompt is expected? If no, don't allow (in fact, just close the window)

Secondly, what does my browser window show? If you're on google.com (or gmail.com) and this appears, that's one thing, but if your browser is showing google.security-check.se then no, don't click anything and just close the window.

Third, even assuming this is all okay, do you want Tripit to have access to view email messages and settings? If all you were trying to do is use your Google account to authenticate, the fact it wants access to view all your messages is highly suspicious. In this particular case (because it's Tripit, a service that parses your email), this is probably your intention, but if it also asked for other permissions -- such as ability to manage contacts and send messages on your behalf -- you might want to think twice.

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Training like this is good, but phishing e-mails can be very devious and training users on the wrong things -- such as trusting "from" addresses, not considering context, and not looking at actual attachment types -- is extremely dangerous. In the worst case, it can train users to click on things they otherwise wouldn't have, due to false confidence obtained by (inadequate) training.

[1] https://i.imgur.com/8mNePZS.png

[2] https://i.imgur.com/tpJMb5n.png

[3] https://i.imgur.com/KfNDuZI.png