Recognize and Combat Scams in Retirement with Robert Siciliano

Cybersecurity expert Robert Siciliano explains how modern scams exploit trust, urgency, and technology—and the habits that can make retirees harder targets.

If you’ve spent 30 or 40 years building your retirement savings, protecting that money involves more than deciding how to invest it.

You also have to protect yourself from anyone who may be trying to steal it.

And the scams we’re dealing with today aren’t necessarily the ones you learned to recognize 20 years ago.

I recently talked with cybersecurity and fraud-prevention expert Robert Siciliano about how scams have changed, why people with accumulated retirement savings can be attractive targets, and what you can do to make yourself harder to scam.

One thing became clear very quickly: protecting yourself isn’t simply a matter of being smart enough to recognize an obvious scam.

Modern fraud increasingly relies on manipulating normal human behavior.

As Robert put it, “It’s not necessarily about your computer being hacked. It’s about hacking humans today.”

Understanding that distinction may be one of the most important steps you can take to protect the money you’ve spent a lifetime accumulating.

A Modern Scam May Start With a Wrong-Number Text

Most people know not to send money to the proverbial foreign prince promising millions of dollars.

Today’s scams can be much more sophisticated.

Robert walked me through one commonly called a “pig butchering” scam. The terminology is unpleasant, but the basic strategy is important to understand because the fraud can develop gradually.

It may begin with something as innocent as a wrong-number text:

Are we still on for lunch tomorrow?

You respond that they have the wrong person.

They apologize.

Then perhaps they ask where you’re from. A conversation starts. Over time, the person on the other end becomes friendly. Messages become more frequent, and eventually the relationship may move to another communication platform.

The scammer isn’t necessarily asking for money at the beginning.

They’re building trust.

Eventually, the conversation may turn to an investment opportunity—often involving cryptocurrency. The victim may be directed to what appears to be a legitimate investment platform and shown apparent gains. That can encourage increasingly large transfers.

The numbers displayed on the screen may look impressive. But when the victim eventually tries to withdraw the money, the supposed investment and the people behind it can disappear.

By then, the losses can be substantial, and potentially unretrievable.

That’s what makes this type of fraud so dangerous. The scam isn’t necessarily a single suspicious email asking you to wire $100,000.

It can be a relationship developed over time.

Artificial Intelligence Makes It Harder to Trust What You See and Hear

Technology is giving scammers more tools to make these interactions convincing.

Robert described the growing use of artificial intelligence, deepfake technology, and voice cloning. Someone communicating with you online may appear to be a real person on a video call. An incoming phone call may display a familiar-looking caller ID. A voice may sound like someone you know.

That changes one of the basic assumptions many of us have relied upon for years.

Seeing someone doesn’t necessarily authenticate them.

Hearing a familiar voice doesn’t necessarily authenticate them.

And seeing a recognizable name on caller ID doesn’t necessarily authenticate the caller.

Robert has experienced this himself. Despite spending decades working in security, he described receiving a call that appeared to come from “Google Security.” The person sounded professional, knew information about him, and came close to convincing a cybersecurity expert to click a malicious link.

That’s worth remembering.

If someone who studies fraud professionally can encounter a convincing scam, our defense can’t simply be, “I’d never fall for that.”

We need a process.

Why Trust Can Become a Vulnerability

Robert calls our natural tendency to trust other people the “human blind spot.”

Human beings generally aren’t wired to approach every interaction assuming the other person is lying. Trust allows families, communities, and businesses to function.

Scammers take advantage of that.

They also know how to create an emotional response.

Your account has been compromised.

You owe money immediately.

Your grandchild is in trouble.

You need to move your money before something happens.

Click this link now or your account will be closed.

The details change, but the objective is similar: create urgency so that you act before you have time to think.

That’s why Robert wants people to become what he calls a “strategic human firewall.”

Instead of assuming an incoming communication is legitimate, learn to recognize the moments when someone is trying to push you into an immediate decision.

Then slow the process down.

Analyze, Authenticate, Act

Robert’s response to these situations is what he calls the Triple A Protocol: Analyze, Authenticate, Act.

1. Analyze

Start by recognizing the emotional trigger.

Is someone creating urgency?

Are they demanding secrecy?

Are they telling you something terrible will happen unless you respond immediately?

If so, don’t let their timetable become yours.

The objective is to interrupt the emotional reaction and give yourself enough time to think analytically about what’s happening.

2. Authenticate

Next, determine whether the person or organization contacting you is actually who they claim to be.

Don’t assume that an email address, phone number, caller ID, photograph, or even a video call is sufficient proof.

Ask yourself whether there’s an independent way to verify the request.

3. Act

Only after you’ve analyzed the situation and independently authenticated the request should you act.

Robert recommends what he calls out-of-band verification.

If your bank appears to call you, don’t automatically use the number provided by the caller. End the call and contact the bank through a number you already know to be legitimate.

If you receive a suspicious request that appears to come from someone you know, contact that person independently using information you already have.

That’s similar to the procedures we use when someone asks us to move money. If I receive an unusual financial request, I want to verify that I’m actually communicating with my client before anything happens.

Analyze. Authenticate. Then act.

That little bit of friction can be extremely valuable when someone is trying to rush you.

Stop Reusing Your Passwords

Behavior is one layer of protection. Your technology is another.

Robert’s first password rule is straightforward:

Don’t reuse the same password across multiple accounts.

If login credentials from one website are exposed in a data breach, criminals may try those same credentials on other services. Reusing a password can therefore turn one compromised account into a much larger problem.

The challenge, of course, is remembering dozens of unique passwords.

Robert recommends using a password manager. A password manager can generate and store long, unique credentials so that you don’t have to memorize a different complicated password for every account.

He also recommends enabling two-factor authentication on important accounts.

Two-factor authentication adds another verification step beyond your password. Depending on the account, that might involve an authentication app, security key, or another verification method.

A stolen password is still a problem. But an additional authentication requirement can create another obstacle between the criminal and your account.

Keep Your Devices and Software Updated

Robert also emphasized keeping your technology current.

That doesn’t necessarily mean buying every new phone the moment it’s released.

It does mean paying attention to whether your computer, phone, operating system, browser, and other software are still receiving security updates.

Older technology can eventually stop receiving important security patches, leaving known vulnerabilities unaddressed.

The practical habit is simple: install legitimate operating-system and security updates when they’re available, and pay attention when a device becomes too old to receive current security support.

The same principle applies here as it does to retirement planning generally.

Maintenance matters.

Don’t Assume Being Smart Makes You Immune

“I can’t believe how stupid I was.”

When Robert recounted a conversation he had with someone who had been defrauded, this line stood out. Being victimized doesn’t necessarily mean someone lacked intelligence. Scammers deliberately use psychological techniques designed to manipulate normal human reactions.

That’s important because embarrassment can create another problem.

If you believe only gullible people get scammed, you may be less likely to recognize your own vulnerability. And if something does happen, embarrassment may make it harder to tell someone quickly.

A better mindset is to assume that everyone needs safeguards.

I teach my teenage daughter not to respond to calls or texts from people she doesn’t know. I have similar conversations with older family members. At Keil Financial Partners, we have procedures for verifying unusual requests involving money.

The details may differ depending on age and circumstances, but the underlying habit is the same:

Don’t assume.

Verify.

Protecting Your Money Is Part of Retirement Planning

We spend a lot of time preparing financially for retirement.

How much can you spend?

When should you claim Social Security?

How should you approach taxes?

How should your money be invested?

Those are important questions.

But if you’ve accumulated a significant amount of money, protecting it from fraud deserves a place in the plan too.

You don’t need to become a cybersecurity expert.

You do need a repeatable process.

Use unique passwords. Consider a password manager. Turn on two-factor authentication where available. Keep your devices and software updated. Be suspicious of manufactured urgency. And when someone unexpectedly asks you to send money, provide information, click a link, or change an account:

Analyze. Authenticate. Act.

You spent decades building your retirement savings.

A few additional security habits may help you protect what you’ve worked so hard to build.

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About the Author:

Jeremy Keil, CFP^®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retire Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

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Additional Links:

• Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
• ProtectNowLLC.com 
• “Cybercrime To Cost The World $12.2 Trillion Annually By 2031” by David Braue, Cybercrime Magazine
• Rober Siciliano on LinkedIn
• LastPass.com – One of many options to use as a password manager

Connect With Jeremy Keil:

• Keil Financial Partners
• LinkedIn: Jeremy Keil
• Facebook: Jeremy Keil
• LinkedIn: Keil Financial Partners
• YouTube: Mr. Retirement
• Book an Intro Call with Jeremy’s Team

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