How to "Break" a Retirement Plan: Part I

August 29, 2025

Welcome to our new series, How to “Break” a Retirement Plan, where we discuss what leads to a retirement plan being categorized as “broken,” ways to fix broken plans, and compliance tips for how to avoid a broken plan in the first place.  

Some retirement plans fail in dramatic fashion. Others fail quietly, over years, until one day the sponsor realizes they’re in deep trouble. In many cases, the issues begin with the foundations of the plan itself: the type of plan chosen, how contributions are handled, the payroll processes that support it. If these building blocks aren’t set up correctly from the start, problems can accumulate until they become costly, or even unfixable. 


Here are some of the most common structural missteps that can put your plan on the wrong track from day one: 


Selecting (or choosing) the Wrong Type of Plan 


There are more than 20 different types of retirement plans available, including 401(k) and profit-sharing plans to defined benefit and cash balance plans. While all of them can be powerful tools, they’re not one-size-fits-all, no matter what some big providers would have you believe. 


If a business selects the wrong type of plan - say, a traditional 401(k) when a cash balance plan would have better matched the owner’s savings goals - it can create participation challenges, unnecessary costs, or compliance problems down the road. For example, a business with high employee turnover may struggle to meet nondiscrimination requirements in a 401(k), while a plan design that ignores owner-only goals could limit tax savings opportunities. 


The takeaway: plan selection should be a strategic decision, not just a box to check. 


Uncashed Distribution Checks 


When participants leave an employer and request distributions, the plan issues them checks. Sometimes, those checks never get cashed. It may seem like a small nuisance, but uncashed checks create major headaches for the employer: 


  • They leave unresolved participant balances on the books. 
  • They increase administrative burden each year as the plan must track and reissue payments. 
  • They expose the plan sponsor to fiduciary risk if a participant claims they never received their money. 

The Department of Labor has made clear that plan fiduciaries are responsible for locating missing participants and ensuring they receive their benefits. Simply letting checks pile up is not an option. 


Late Deposit of Employee Contributions 


Employee salary deferrals must be deposited into the plan as soon as they can reasonably be segregated from the employer’s assets. For large employers, this is often the same day as payroll. For smaller employers with fewer than 100 participants, the Department of Labor offers a safe harbor of seven business days


Late deposits, even if unintentional, are considered prohibited transactions. Prohibited transactions are subject to correction, excise taxes, and IRS/DOL scrutiny. Repeated lateness can even trigger an audit. 


This is one of the most common ways otherwise healthy retirement plans get flagged for compliance issues. Employers need strong internal processes to ensure contributions are deposited promptly, every time. 


Payroll Errors 


Payroll is the engine that drives a retirement plan and is accountable for 90% of plan issues. Even small errors here can ripple out into major compliance failures. Examples include: 

  • Failing to apply the correct match formula. 
  • Deducting Roth contributions but depositing them as pre-tax. 
  • Leaving out certain forms of compensation (e.g., bonuses or overtime) when calculating contributions. 
  • Missing deferrals for new hires or rehired employees. 
  • Misclassifying employees as independent contractors 

These mistakes don’t just affect one person’s account balance: they can cause the plan to fail nondiscrimination testing or create an operational error that requires costly corrections. Since payroll is often outsourced, miscommunication between payroll providers and plan administrators is a frequent root cause. 


The Bottom Line: Build the Right Foundation from the Start 


Many retirement plan problems can be traced back to structural missteps such as plan design, contribution handling, and payroll processes. On the surface, these may seem like “back-office” details, but they form the bedrock of a compliant and effective plan. 


If you get these basics right from the start, your plan is far more likely to run smoothly for years to come. If you don’t, even the best investment lineup or participant education program won’t save you from costly corrections and potential regulatory trouble. 


The good news? With proper guidance from experienced plan administrators, these risks can be identified and resolved early, before they snowball into something unmanageable. Everyone makes mistakes, and the government actually wants you to fix them. Experienced TPAs and ERISA attorneys can guide you through the correction process, typically at a much lower cost than if the government uncovers the mistake on its own. 

September 15, 2026
The Challenge Sometimes the most expensive retirement plan mistakes aren't dramatic. They're quiet. A former client of ours changed retirement plan providers following an acquisition several years prior. On the surface, everything appeared to be operating normally after moving to the new provider: employees continued making contributions to the plan, the plan’s investments remained in place, and the business continued its normal operations. Then another merger opportunity came along. As part of their due diligence process, the buyers reviewed the retirement plan. What they found immediately raised concerns. The annual Form 5500 filings required by ERISA law had not been submitted for several years. That also meant that none of the required compliance testing had been completed, and routine administrative responsibilities had also gone undone. What had started as a routine review quickly became a significant obstacle to completing the business sale. The Hidden Risk Many employers assume that once a retirement plan provider is hired, responsibility for the plan’s ongoing administration has effectively been transferred to that provider. But a plan sponsor is never completely relieved of its responsibility to oversee the plan. Even when outside providers are hired to handle filings, testing, recordkeeping, or other administrative functions, the employer still needs to make sure those responsibilities are being fulfilled. At the same time, there is an important difference between a provider that simply waits for the employer to supply information and one that actively works with the employer to make sure the plan stays on track. In this case, some of the missing work may have resulted from information requested by the provider that was never supplied by the employer. Technically, the employer still had a responsibility to provide that information and ensure the work was completed. But years of required administration should not quietly disappear into a communication gap. A proactive administrator follows up. If the usual contact isn’t responding, they escalate the issue. They make sure the appropriate people understand what is outstanding, why it matters, and what could happen if it isn’t addressed. Retirement plans require ongoing attention every year, including government filings, compliance testing, participant administration, documentation, and, when necessary, operational corrections. When those responsibilities are neglected, the consequences may not become obvious immediately. Instead, problems can accumulate quietly in the background until an IRS inquiry, Department of Labor investigation, audit, or—as in this case—a business transaction suddenly exposes years of unresolved issues. The prospective buyer made it clear that the retirement plan issues needed to be addressed before the transaction could move forward. The Rescue Knowing we had previously administered their plan, the current company leadership contacted us. Our first step was to determine the full scope of the problem. The timing made the situation particularly challenging. This wasn’t simply a retirement plan cleanup project. A business transaction was underway, and the company needed answers quickly. We assembled a team to determine the full scope of the problem and begin developing a path forward. Because we have deep experience with taking over neglected plans, we were able to separate perceived problems from actual compliance issues and reconstruct the plan's history. In reviewing the prior documentation, we identified exactly which administrative functions had been completed and which had been missed. We gathered historical payroll and participant data and developed a comprehensive correction strategy. Having access to historical plan records was especially important. Retirement plan problems may not surface until years after the underlying event, making good record retention critical. If you’re curious about how long to hold onto plan documentation, please see our blog post here . The final correction effort proved to be far more manageable than originally feared. Instead of allowing uncertainty around the retirement plan to continue hanging over the transaction, the employer now understood what had actually gone wrong, what needed to be corrected, and what steps were required to move forward. The Outcome With the correction efforts clarified and a clear roadmap in place, the employer was able to begin correcting the plan and continue moving toward its business transaction. More importantly, the company avoided entering the acquisition process with unresolved retirement plan liabilities hanging over or ruining the deal. The experience also reinforced an important lesson: Changing retirement plan providers doesn't eliminate administrative responsibilities. But it also demonstrated why the quality of the administrator matters. A good retirement plan administrator doesn’t simply process the information that arrives. They help make sure the information arrives in the first place. The Lesson: Oversight Is a Shared Process Employers ultimately have a responsibility to oversee their retirement plans, even when they hire professionals to handle much of the day-to-day work. That doesn’t mean the employer should have to become a retirement plan expert or personally track every filing deadline and compliance requirement. That’s one of the reasons experienced administration matters. A proactive provider should help keep the employer informed, identify missing information, follow up when something is outstanding, and escalate issues before a missed request becomes a missed filing—or several years of missed filings. The cost of failing to do so can extend well beyond an annual administration fee: Missed filings and potential penalties Incomplete compliance testing Corrective work Additional professional fees Delayed business transactions Uncertainty during mergers and acquisitions  By the time those costs appear, they can far exceed whatever might have been saved by choosing a lower-cost service model. That’s why retirement plan administration shouldn’t simply be viewed as paperwork. It should be viewed as an ongoing partnership in managing risk.
August 18, 2026
The Challenge A business owner came to us after receiving confusing news from their retirement plan actuary. Their Defined Benefit (Cash Balance) Plan had performed exceptionally well over several years; strong investment returns seemed to have created what’s called an overfunded Plan. While it seems like a positive name, an overfunded plan can create excessive and unexpected tax liabilities. So, their actuary recommended terminating the Plan by transferring the excess assets into the company's other Plan, a 401(k)/Profit Sharing Plan, before eventually closing both Plans, a lengthy and complicated process.
July 15, 2026
As we wrap up the second quarter of 2026, one trend continues to stand out: retirement plans are becoming increasingly specialized. Whether driven by changing regulations, unique workforce structures, or evolving business goals, employers are finding that a one-size-fits-all approach simply doesn't work. This quarter, we explored the unique retirement plan challenges facing several industries—including medical and dental practices, construction companies, architecture and design firms, wineries, and California employers navigating CalSavers requirements. We also continued our series on the hidden risks of low-quality retirement plan services, highlighting how operational complexity, fragmented accountability, and misaligned incentives can create costs that extend far beyond administrative fees. For employers still evaluating their retirement plan options, we also discussed opportunities that many business owners overlook, including the ability to establish retirement plans after filing a tax extension and potentially generate meaningful tax savings. Below is a recap of the articles we published this quarter. We hope they provide practical insights to help you reduce risk, improve plan performance, and make more informed retirement plan decisions.
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