If you’re planning to retire, step away from private practice, or transition out of law for any reason, there’s one topic you cannot afford to misunderstand: extended reporting periods, often referred to as “tail coverage.”

Recently, I read an article published on the Professional Liability Underwriting Society blog, authored by Lucas Roberts, that does an excellent job of reinforcing an important—and often overlooked—point about tail coverage. It’s a point worth emphasizing because getting it wrong can leave you exposed at exactly the wrong time.

What an Extended Reporting Period Really Does

Many attorneys assume that purchasing tail coverage (or qualifying for a free tail) automatically protects them from any issues that arise after their policy ends. That assumption can be dangerous.

An extended reporting period does not extend the time to report claims you already know about.

Instead, it allows you to report claims that are first made against you and first become known to you during the extended reporting period—after your policy has ended.

That distinction matters.

Known Claims Must Be Reported Before You Tail Out

Before canceling your policy or requesting tail coverage, you must take the time to review your files carefully. Any claim—or even a potential claim—that you are aware of must be reported to your carrier before the policy ends.

This is true whether you are:

• Purchasing tail coverage, or
• Qualifying for a free tail under your policy

Failing to report known issues before tailing out can result in a claim being denied later due to late reporting—even if you have an extended reporting period in place.

Why This Step Is So Important

Here’s the situation you want to avoid:

You retire or leave practice.
You tail out your policy.
A claim surfaces during the extended reporting period.
You report it—only to learn that the carrier declines coverage because the issue was known before the policy ended and was never reported.

At that point, you may find yourself personally responsible for a claim you assumed was covered.

The Right Way to Protect Yourself

Before you tail out:

1. Review your open and closed files carefully
2. Identify any actual or potential claims
3. Report those issues to your carrier before canceling the policy
4. Then proceed with tail coverage—free or purchased

Taking these steps helps ensure that the coverage you believe you have is actually there when you need it.

Final Thoughts

Extended reporting periods are a valuable protection—but only when they’re understood and used correctly. Don’t let a technical misunderstanding undo years of careful risk management.

If you’re approaching retirement or considering a transition out of practice, now is the time to review your coverage and make sure everything is handled properly.

Cyber insurance is still one of the most misunderstood types of coverage I see — especially among law firms.

Many firms assume they’re protected…
until something actually happens.

Unfortunately, that’s often when they discover the coverage they thought they had doesn’t respond the way they expected. Let’s clear up some of the most common cyber insurance myths law firms continue to believe.

Myth #1: “Our General Liability Policy Covers Cyber Incidents”

This is one of the most common — and most dangerous — assumptions.

In most cases, general liability insurance does not cover cyber incidents.
General liability is designed for things like bodily injury, property damage, or advertising injury — not data breaches, ransomware, or network intrusions.

If a client’s personal information is compromised, a general liability policy typically won’t respond. That’s where cyber insurance comes in — if you have it set up correctly.

Myth #2: “We Have an IT Company, So We Don’t Need Cyber Insurance”

IT support is critical — but it’s not a substitute for insurance.

Think of it this way:

• IT helps prevent problems
  
• Insurance responds when prevention fails
  

Even the best security systems can be bypassed. Phishing emails, compromised passwords, vendor breaches, and human error still happen every day. When they do, cyber insurance helps cover the financial fallout — not your IT provider.

Myth #3: “We’re Too Small to Be a Target”

This one couldn’t be further from the truth.

Today, size doesn’t matter when it comes to cyber attacks. In fact, smaller law firms are often easier targets:

• Less money spent on cybersecurity
  
• Fewer internal controls
  
• Outdated systems
  
• Easier access points for attackers
  

Hackers aren’t always looking for the biggest payout — they’re looking for the path of least resistance.

Myth #4: “Cyber Insurance Is Just for Ransomware”

Ransomware may get the headlines, but cyber insurance covers much more than that.

Depending on the policy, cyber coverage may help with:

• Data breaches
  
• Business interruption
  
• Client notification requirements
  
• Forensic investigations
  
• Legal and regulatory costs
  
• Credit monitoring services
  
• Crisis management and reputation support
  

Cyber incidents can affect your firm long after systems are restored — and the costs add up quickly.

The Real Issue: Understanding What Cyber Insurance Does (and Doesn’t) Cover

The biggest issue isn’t whether a law firm has cyber insurance.

It’s whether they understand:

• What their policy actually covers
  
• What it excludes
  
• How it would respond in a real-world incident
  

If you’re not sure how your policy would work during a data breach or cyber attack, that’s usually a sign it’s worth reviewing.

Every January, I see the same insurance mistake. And it usually doesn’t show up until there’s a problem.

It’s not that people don’t have insurance. Most do. The issue is the assumption that because a policy renewed, the coverage must still be right for the business. Unfortunately, that assumption can be costly.

Renewed Doesn’t Always Mean Reviewed

Most insurance policies renew automatically. That convenience is helpful, but it can also be misleading. A renewal doesn’t necessarily mean anyone reviewed your coverage. In many cases, it simply means the paperwork rolled over from the previous year.

The challenge is that businesses don’t stay the same from year to year.

Over the course of twelve months, you may hire employees, take on new types of clients, rely more heavily on technology, or store more sensitive data. Each of those changes can affect your risk. But unless someone actually looks at the policy, your coverage remains exactly where it was.

Where Problems Often Appear

I’ve seen situations where someone believed they were fully covered — and technically, they were. Just not for the situation they were facing.

The issue usually isn’t negligence. It’s the assumption that “renewed” meant “reviewed.” When a claim happens, that’s not the time anyone wants to discover that something changed and the policy didn’t keep up. At that point, the decision has already been made.

Why January Is the Right Time to Look

The start of the year is actually a good time to pause and ask a simple question: does my insurance still match how my business operates today?

That doesn’t automatically mean you need more coverage. In many cases, it simply means you need the right coverage for how your business has evolved.

A short review at the beginning of the year can help identify gaps, outdated limits, or assumptions that no longer apply. More importantly, it can prevent an expensive surprise later.

A Small Step That Can Make a Big Difference

Insurance is designed to protect you when something unexpected happens. Making sure your coverage reflects how your business actually operates is one of the simplest ways to make sure it does what it’s supposed to do.

A little time spent reviewing things now can go a long way toward avoiding problems later — and that’s something I’d always rather help people prevent.

In today’s digital world, cyber threats aren’t just targeting the big corporations you see on the news. They’re hitting small businesses every single day — law firms, chiropractors, retailers, accountants, nonprofits, and anyone who handles sensitive information.

And here’s the scary part:

It only takes one wrong click.
One outdated system.
One overlooked vulnerability.

And suddenly… it’s game over.

But not today.

That’s exactly why I wrote Game Over? Not Today! Power-Ups for Cyber Liability and Security — a practical, no-fluff guide built to give business owners the tools they need to stay protected in a world where cyber threats evolve faster than ever.

Below are four of the biggest “power-ups” from the book — the ones that can make or break your protection.

Power-Up #1: Your Employees

Your team can be your strongest defense… or your biggest vulnerability.

Most cyber incidents don’t start with sophisticated hackers breaking into a network. They start with everyday mistakes — clicking a suspicious link, opening a bad attachment, or ignoring a warning sign.

In the book, I walk you through simple, repeatable habits your employees can build to:

• Spot phishing emails
  
• Identify strange links
  
• Recognize suspicious account activity
  
• Report problems before they escalate
  

This is the kind of daily awareness that saves businesses from major losses.

Power-Up #2: Review Your Cyber Insurance Regularly

Most business owners purchase a cyber liability policy…
and then never look at it again.

But threats change.
Your business changes.
Your technology changes.

And if your coverage doesn’t keep up, you may not be protected the way you think you are.

A quick annual review can help you:

• Close dangerous gaps
  
• Update limits based on growth
  
• Make sure exclusions aren’t leaving you exposed
  
• Align your coverage with your current risk level
  

It’s one of the simplest and most impactful steps you can take.

Power-Up #3: Partner With the Right Cybersecurity Experts

You don’t have to go it alone.

The right cybersecurity partner gives you:

• Better tools
  
• Stronger defenses
  
• Real-time monitoring
  
• Faster responses
  
• And in many cases… better insurance terms
  

Not all cybersecurity providers are equal, so inside the book, I break down exactly what to look for — and what to avoid — so you get real value instead of empty promises.

Power-Up #4: Have a Clear, Practical Plan in Place

Every business needs a clear set of cybersecurity fundamentals, including:

• An incident response plan
  
• A documented process for who does what in a cyber event
  
• A genuine understanding of what your policy actually covers
  
• A checklist to make sure nothing slips through the cracks
  

No jargon. No overwhelm. Just practical steps that keep your business confident and prepared.

Ready to Protect Your Business?

If you want the peace of mind that comes from knowing your business is prepared, protected, and ready for whatever comes your way, now’s the time to take action.

📘 Download Game Over? Not Today! Power-Ups for Cyber Liability and Security and get the tools you need to stay ahead of evolving threats.

Today I wanted to share an important reminder that too many attorneys learn the hard way: renewal application management matters. In fact, it can make the difference between keeping decades of prior acts coverage… or losing it overnight.

A Real Conversation With a Real Consequence

I recently spoke with an attorney who was considering switching their legal malpractice coverage over to us. They told me they’d had continuous coverage for more than 20 years — never a lapse, never a break.

But when I reviewed their current policy, something immediately stood out:

Their retroactive date was only a couple of years old.

If you’ve carried uninterrupted coverage for two decades, that should never happen. So I asked, “What’s going on with this retro date?”

The answer was painful.

A few years back, their firm submitted their renewal application late. The carrier still issued a quote — but with a new retroactive date. That single change wiped out nearly 20 years of prior acts coverage. One late renewal. One technicality. A massive loss of protection.

Don’t Let This Happen to Your Firm

We’re heading into the busy season — holidays, year-end work, family commitments, and a general whirlwind of “I’ll get to it later.” But your legal malpractice renewal application is not something to push back.

Treat it like you would a statute of limitations.
Put it in your calendaring system.
Enter reminders at 120 days, 90 days, 60 days, and even 30 days before renewal.

Whatever you do, don’t assume you can complete your application on December 30 for a January 1 renewal and expect the carrier to turn it around in time. Most carriers need 20–25 days to properly underwrite your file. You might get lucky once — but luck is not a strategy.

The Stakes Are Too High

Imagine carrying legal malpractice insurance your entire career — 20 or 30 years — only to lose all those prior acts because your renewal was late by a day or two.

It happens.
It’s brutal.
And it’s completely avoidable.

Final Thoughts

If you take nothing else from this story, take this:
Calendar your renewal like a critical deadline.
Protect your prior acts coverage.
Don’t give a carrier any reason to strip away decades of protection simply because paperwork arrived late.