re: Weird blackmail email I got

Here's how I dealt with a scammer earlier on a dating app

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The one thing that freaked me out on a few of those is they had old passwords for some things like my work outlook.

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That’s how they get a lot of people. In reality, they got your password from some sort of data breach (there have been plenty of major ones over the years). They buy a register of names, email addresses, passwords, and whatever else is available.

Which leads me to another point - if you have an email account that’s been using the same password for multiple years and you’ve used that password for any other websites/services, chances are pretty good that somebody, somewhere has access to your email account.

I’m not one of those password complexity freaks, but everyone should really have a separate password for their email accounts with 2FA enabled, if available, to prevent identity theft.