Hi, I’m Dear 404 — the advice column that won’t redirect you

I’m your resident information security devotee with a dial-up-era attitude and a mission to help you navigate today’s digital world. Think Dear Abby with root access and zero judgment.

Here’s how it works:

  • Ask me anything—big or small. From “How do I know if an email is phishing?” to “What’s the safest way to share files?” no question is too basic or too advanced.
  • Stay anonymous. Your questions are completely confidential. I am protected behind UTORid login but rest assured your questions are NOT linked to your identity.
  • Check back monthly. On the 28th of every month, I’ll feature one question (and answer) right here on the Information Security website.

Since it’s anonymous, I can’t send an alert when your question goes live—you’ll just need to pop back in and see if it was chosen.

At the heart of Dear 404 is a safe, welcoming space to explore cybersecurity, privacy and digital safety without fear of asking the “wrong” question. Whether you’re worried about your password habits, curious about how cookies really work or just trying to figure out what “multi-factor authentication” means—I’ve got your back.

So fire up your questions and let me help you stay secure, savvy and maybe even relive a few throwback tech moments along the way.

Sincerely,
4[0‿0]4

Have a question for 404?

Get to know me:
Dear 404

Robot 404 holding a folder

You’ve probably heard of Dear Abby-the advice column where people wrote in with life’s problems. Think of me as the digital version of that. I’m Dear 404, your-go-to guide for navigating the weird, confusing and occasionally alarming world of cybersecurity. My name comes from one of the web’s most famous messages; “404: Page Not Found.” It pops up when something’s missing, lost or just plain not working—which felt like the perfect metaphor for what I do. When something goes wrong online. I’m here to help you find what’s missing and get back on track.

What’s the best way to access files remotely?

Our latest question:

I don’t work in IT. I keep hearing about ‘data classification’ in meetings, especially when we’re looking into vendors or new systems. What exactly is data classification, and why does it always come up during these conversations?

— Baffled by Buzzwords

More answers from 404