Tax Due Diligence Checklist for M&A

Tax due diligence is a critical step in mergers and acquisitions (M&A) to identify risks, avoid unexpected tax liabilities, and ensure smooth deal execution. With the U.S. M&A market projected to reach $1.17 trillion by 2025, thorough tax reviews are more important than ever. Here’s what tax due diligence involves:

Key Areas to Focus On:

  • Tax Risks & Compliance: Review past tax filings, audit history, and compliance at federal, state, and local levels to spot potential liabilities.
  • Tax Attributes: Assess net operating losses (NOLs), tax credits, and other attributes that could impact deal value.
  • Audit History & Disputes: Investigate ongoing or past tax audits, disputes, and communications with tax authorities.
  • Current Liabilities: Analyze financial statements for immediate and deferred tax obligations.
  • Deal Structuring: Use tax indemnities, escrows, and pre-closing remediation to manage risks.

Quick Takeaways:

  • 47% of deals fail due to due diligence issues, many related to taxes.
  • Tax liabilities can derail deals or lead to diminished shareholder value.
  • Addressing tax risks early ensures smoother negotiations and better outcomes.

By focusing on compliance, liabilities, and opportunities, tax due diligence helps protect both buyers and sellers and ensures a successful M&A transaction.

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Review Tax Returns and Compliance History

Effective tax due diligence begins with a thorough review of the target company’s past tax filings. This process helps identify compliance patterns, potential risks, and tax attributes that could influence the financial aspects of the deal.

Check Federal, State, and Local Tax Returns

Examining tax returns across federal, state, and local levels is essential to assess the target company’s compliance standing. Buyers should gather and review all relevant tax documents, including returns, audit reports, IRS correspondence, and any supporting records for tax positions taken. Ideally, this review should cover at least three to five years of filings to detect recurring issues.

State tax compliance often reveals unexpected challenges during due diligence. Businesses may unknowingly trigger nexus obligations in states where they operate, leading to unfiled returns and accrued liabilities. Sellers can mitigate these risks by conducting a pre-sale nexus study to identify filing requirements and quantify potential exposures from unfiled returns. For buyers, understanding the target’s nexus status in all states where it operates is critical.

Review Sales, Use, and Employment Tax Filings

Beyond income taxes, reviewing sales, use, and employment tax filings is crucial to avoid unforeseen liabilities. Incomplete sales and use tax compliance can disrupt deals. Certain warning signs, such as consistently late filings, may indicate deeper issues like financial struggles, weak internal controls, or a history of non-compliance. Similarly, unresolved tax debts can signal financial mismanagement and create immediate concerns for buyers.

Employment tax compliance also requires close examination. Underreported wage taxes can result in significant adjustments, especially if payroll processes are inadequate. It’s also essential to evaluate contractor classifications, as misclassifications can lead to penalties and back-tax obligations. The U.S. Department of Justice emphasizes the importance of risk-based due diligence, stating, "Risk-based due diligence is particularly important with third parties and will also be considered – in assessing the effectiveness of a company’s compliance program". Buyers should analyze the target’s tax exposure to quantify risks and explore remediation options. This groundwork is critical for uncovering both risks and opportunities related to tax compliance.

Find Tax Attributes and Opportunities

After assessing compliance history, the next step is to identify tax attributes and potential opportunities that could add value to the deal.

Tax attributes like net operating losses (NOLs) and tax credits can provide significant tax savings, though their use may be limited. For example, Section 382 can restrict the utilization of acquired losses following major ownership changes.

Deal Structure NOL Transfer Impact
Stock Purchase NOLs transfer with the entity but may be subject to Section 382 limitations due to ownership changes.
Asset Purchase NOLs usually remain with the seller and do not transfer to the buyer.

Due diligence on NOLs involves verifying their origin, checking expiration dates, and evaluating the effects of any prior restructuring. Additionally, buyers should look into pre-change tax credit carryovers and carryforwards of disallowed business interest deductions under Section 163(j). Engaging a tax professional to conduct a Section 382 ownership study is recommended to monitor ownership changes and determine applicable limitations.

The structure of the deal – stock versus asset purchase – greatly impacts how tax attributes are treated. In stock purchases, the buyer inherits the target’s tax attributes, including carryover credits that can offset future liabilities. In contrast, asset purchases typically do not transfer these credits, reducing potential tax-saving benefits.

Check Audit History and Tax Disputes

Understanding how a company interacts with tax authorities can reveal risks that might surface after an acquisition. Carefully reviewing audit history and any ongoing tax disputes gives buyers a clearer picture of potential challenges and their financial implications.

Review Past and Current Tax Audits

Start by examining the company’s audit history. Look at how often audits have occurred, what areas they covered, and how they were resolved. Frequent audits or recurring issues might signal deeper compliance problems or operational practices that raise red flags. For instance, if a company has faced multiple audits recently, it could indicate aggressive tax strategies or procedural weaknesses that attract regulatory attention. Pay special attention to adjustments made during audits, especially those tied to aggressive tax positions that resulted in penalties, fines, or interest charges.

It’s also important to consider how the IRS has updated its audit processes. Newer techniques, like the use of data analytics and artificial intelligence, allow for more targeted scrutiny in certain areas. If the company is currently under audit, clarify the situation immediately to avoid unexpected adjustments later. This step is crucial, as unresolved issues could lead to significant post-acquisition complications.

This review sets the foundation for analyzing the company’s communications with tax authorities.

Check Communications with Tax Authorities

A company’s correspondence with tax authorities can provide valuable insights into its compliance practices and highlight potential risks. Request documentation of all communications with the IRS and state tax agencies, focusing on notices related to unfiled returns, late payments, or requests for additional information.

Unresolved tax disputes are particularly risky in mergers and acquisitions. They could lead to substantial adjustments, penalties, and interest charges – liabilities that the buyer might inherit. Review any settlement agreements or payment plans in place, as these could continue after the acquisition and impact cash flow.

If the company operates internationally, this review becomes even more complex. Businesses with overseas activities may face scrutiny from multiple tax jurisdictions, each with its own rules and dispute resolution processes. Understanding these dynamics is key to assessing the full scope of potential tax risks.

By clarifying these communications, buyers can negotiate safeguards such as tax escrows to mitigate risks.

Use Tax Escrows to Reduce Risks

Tax escrows offer a practical way to manage tax-related uncertainties uncovered during due diligence. These arrangements protect both buyers and sellers by setting aside funds to address potential liabilities without stalling the transaction.

Escrow coverage should specifically address the risks identified during the review, such as unpaid sales taxes, unresolved audit findings, or compliance gaps. The escrow amount should account for not only the direct tax liabilities but also any associated penalties and interest.

For larger exposures, tax liability insurance can be a viable alternative to traditional escrows. With premiums typically ranging from 1% to 6% of the coverage limit, this option can free up capital while still providing protection.

When setting up an escrow agreement, clearly define the liabilities it covers, the disclosure requirements, the seller’s liability limits, and the process for resolving disputes. In cases of significant state tax liabilities, sellers might consider resolving these issues pre-closing through voluntary disclosure agreements, which can help streamline the transaction.

A well-structured escrow arrangement not only safeguards the buyer but also ensures the seller’s funds are released promptly once the risks are resolved. This balanced approach keeps the deal moving forward while providing adequate protection against potential tax issues.

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Review Tax Liabilities, Credits, and Contingencies

Assessing the target company’s tax obligations and benefits is crucial for spotting risks that might influence the deal’s value. This builds on earlier steps like reviewing tax returns and audit history, shifting focus to current liabilities and potential tax benefits.

Check Current and Deferred Tax Liabilities

Start by examining the company’s financial statements to uncover both immediate and future tax obligations. Current tax liabilities reflect what the company owes now, while deferred tax liabilities point to future payments that could strain cash flow over time.

Dig into tax reserve calculations and accruals. Review workpapers and disclosures to identify unrecognized tax benefits or questionable tax positions that might not hold up under regulatory scrutiny. Companies sometimes adopt aggressive tax strategies that look solid on the surface but could lead to substantial liabilities later.

Pay close attention to changes in tax provisions. For instance, a sudden increase in deferred tax assets may suggest the company is banking on future profits to claim tax benefits – an assumption that could backfire if market conditions shift. Robust supporting documentation is essential here. Weak or incomplete records can lead to trouble during audits, turning estimated liabilities into much larger financial hits.

This review complements earlier compliance checks, offering a deeper understanding of potential future exposures tied to the company’s tax strategy.

Confirm Tax Credits and Incentives

Verify the legitimacy and documentation of any tax credits the company claims, such as R&D, employment-based incentives, or location-specific relief. Ensure the necessary paperwork is in place and determine whether these benefits can transfer to the buyer post-acquisition.

R&D credits under Section 41 are a common example but often face challenges. Companies must provide detailed records, including time tracking and documentation of qualifying activities. Employment-based incentives may require ongoing compliance with specific hiring or retention conditions, and some include clawback provisions that could force repayment if those terms aren’t met after the deal closes.

Evaluate the status of net operating losses (NOLs), credits, or deferred tax assets, keeping in mind that ownership changes can limit their usability. Under Internal Revenue Code Sections 382 and 383, strict rules cap how much of these benefits new owners can use annually. These insights help shape the overall tax strategy for the transaction.

"Tax due diligence serves as a critical lens through which we discover and quantify potential tax risks in M&A transactions. These findings often impact the deal structure, escrow holdbacks, indemnification, and determine what conditions are needed to resolve tax issues." – Bob Houston, Tax and M&A Leader

Find Tax Penalties or Liens

Uncover hidden penalties and liens by conducting thorough lien searches, including checks for UCC liens, federal and state tax liens, and judgment liens. These searches can reveal issues not recorded in the company’s books but that could become the buyer’s problem.

Federal and state tax liens are particularly concerning since they can attach to all company assets and survive ownership changes. Confirm with tax authorities that no liens exist, even if the company’s records indicate otherwise. Liens can sometimes be filed without the company’s knowledge, especially in cases involving payroll or sales tax disputes.

Review penalty and interest accruals, as these are often underestimated or not updated regularly in financial statements. Penalties for late filings, accuracy-related issues, and interest on unpaid taxes can quickly snowball, far exceeding the original tax amount owed.

For companies with international operations, additional layers of complexity arise. Overseas activities may involve withholding taxes, VAT obligations, or customs duties, each with unique penalty structures and lien procedures depending on the jurisdiction. It’s essential to review compliance in every country where the company operates.

While discovering penalties or liens doesn’t automatically derail a deal, it does require careful planning. These issues can often be addressed through purchase price adjustments, escrow arrangements, or seller indemnifications – provided they’re identified during due diligence rather than after closing. This information lays the groundwork for structuring the deal to address tax risks effectively.

Structure the Deal to Handle Tax Risks

Once you’ve completed due diligence and identified potential tax risks, the next step is structuring the deal to address these issues. This stage is where your findings are turned into actionable protections and negotiation strategies to safeguard your investment.

Calculate Tax Exposures

Tax due diligence helps you understand a company’s tax exposure while uncovering opportunities to reduce liabilities. This process typically involves three key steps to paint a full picture of potential risks.

First, prepare a focused information request list. This should cover both general requirements and transaction-specific details. Request items like previously filed tax returns, financial statements, and the company’s income tax provision. Follow this up with management interviews – speak directly with the target company’s tax director or chief tax officer to gain deeper insights.

Next comes the quantitative analysis. Here, your due diligence team reviews all collected data to calculate the potential tax exposure in dollar terms. This is critical for determining how tax risks could impact deal pricing.

During this phase, buyers often uncover liabilities tied to state income tax or sales and use tax compliance. Many companies struggle to manage multi-state tax obligations or track nexus-creating activities. These gaps highlight why tax considerations must be integrated into every financial aspect of the deal, from net debt calculations to tax assets.

Once exposures are quantified, you can use tools like indemnities and escrow arrangements to protect against potential liabilities.

Add Tax Indemnities and Escrows

To shield yourself from unexpected tax liabilities that could arise after the deal closes, tax indemnities and escrow arrangements are essential. These mechanisms ensure that the seller remains financially responsible for pre-closing tax issues while providing a safety net to address any surprises.

When drafting indemnity clauses, make sure they cover penalties, interest, and related fees for the specific tax risks identified during due diligence. These indemnities should extend beyond the standard representation and warranty period to account for issues that may surface later.

Escrow holdbacks are another layer of protection. By setting aside funds in escrow, you have immediate access to resources if tax liabilities emerge. The amount and duration of the escrow should align with the quantified tax risks and applicable statutory limitations. Don’t forget to account for costs associated with Voluntary Disclosure Agreements (VDAs), as these can be significant and should be factored into your escrow calculations.

Ensure that the final closing statement includes accurate tax accruals and that income taxes are properly accounted for as part of the closing indebtedness. Engaging tax professionals early in the process is crucial to get these calculations right.

Once these protections are in place, the focus shifts to addressing pre-closing tax obligations.

Handle Pre-Closing Tax Obligations

Resolving tax issues before closing is essential to avoid carrying them into post-acquisition operations and to maintain compliance.

Start by correcting any accounting methods pre-closing to prevent post-closing adjustments under Section 481(a). Negotiate control over the preparation and filing of these changes, or at least secure strong review rights.

If the company has Net Operating Losses (NOLs) or Deferred Tax Assets, verify their accuracy and ensure proper documentation is in place. Keep in mind that ownership changes could trigger limitations under Internal Revenue Code Sections 382 and 383.

Carefully review pre-closing and straddle tax returns, especially those spanning the closing date. Properly allocate income and expenses between pre-closing and post-closing periods to avoid disputes later.

Assess the company’s current tax practices and decide whether to retain the existing tax provider or implement new systems for compliance. This step ensures you have the right resources in place for a smooth transition.

Finally, secure compliance confirmations from relevant tax authorities. Obtain debt and filing confirmations from municipalities, verify property tax compliance, and ensure there are no outstanding liabilities with state tax departments.

For companies using tax incentives or special programs, confirm compliance with the terms of these benefits and notify tax offices of any ownership changes. Be aware that some incentives include clawback provisions, which could require repayment if post-closing conditions aren’t met.

"Tax due diligence serves as a critical lens through which we discover and quantify potential tax risks in M&A transactions. These findings often impact the deal structure, escrow holdbacks, indemnification, and determine what conditions are needed to resolve tax issues."
– Bob Houston, Tax and M&A Leader

Conclusion and Key Takeaways

Tax due diligence plays a vital role in mergers and acquisitions (M&A), offering a structured approach to uncover, evaluate, and address tax risks before they escalate into costly problems.

Tax Due Diligence Checklist Summary

Successful tax due diligence hinges on three main pillars: gathering detailed information, conducting interviews with management for context, and performing quantitative analyses that turn findings into actionable insights. This process not only reviews the target company’s past performance but also helps identify potential risks and opportunities.

The checklist focuses on seven key areas, including tax return reviews, compliance history, audit records and disputes, current liabilities, and deal structuring for protection. By thoroughly evaluating federal, state, and local tax obligations, acquirers can implement safeguards to minimize exposure. Aligning these steps with detailed reviews of tax returns, audits, and liabilities ensures a robust framework for risk management.

"When business leaders ask me the ideal time to get the tax department involved in integration planning, I tell them ‘When you sign the letter of intent.’" – Pam Beckey, partner, Deloitte Tax LLP and leader of its Post-Merger Integration practice

These essential steps pave the way for effective risk management and seamless integration after the deal closes.

Benefits of Complete Tax Due Diligence

Expanding on the checklist, thorough tax due diligence offers more than just risk mitigation – it can also boost the overall value of a deal. Bain & Company’s 2023 M&A survey found that nearly 40% of respondents identified high-quality due diligence as the key to a successful transaction. Conversely, poor due diligence has been a major cause of deal failures.

The financial stakes are significant. For instance, global tax abuse results in over $427 billion in losses annually, highlighting the importance of compliance and detailed risk assessments. Companies that prioritize comprehensive tax due diligence can avoid these pitfalls and strengthen their financial position.

Beyond avoiding risks, a detailed tax review can reveal hidden value. Identifying and preserving assets like Net Operating Losses (NOLs) and tax credits can provide substantial post-acquisition benefits, potentially offsetting the cost of the due diligence process itself.

Additionally, a thorough approach helps prepare for smooth post-closing integration. By addressing compliance gaps, accounting issues, and system requirements early, companies can minimize disruptions and ensure a more efficient transition.

Complete tax due diligence also supports the creation of protections such as indemnities, escrow arrangements, and pre-closing remediation plans, converting potential liabilities into manageable risks.

For businesses navigating complex M&A, especially those with multi-state or international operations, investing in a detailed tax due diligence process can lead to fewer surprises, better deal terms, and a smoother integration.

For expert advice on managing M&A and tax due diligence, visit Growth Shuttle’s business advisory services at https://growthshuttle.com.

FAQs

What are the main tax risks to watch for during M&A due diligence, and how can they affect the transaction?

During mergers and acquisitions (M&A), several tax risks can surface, potentially complicating the deal. These include unfiled or late tax returns, outstanding tax liabilities, aggressive tax strategies, transfer pricing issues, and exposure to back taxes or penalties. If left unchecked, these problems can lead to unexpected costs, diminish the transaction’s value, or even derail the entire deal.

Conducting thorough tax due diligence is essential to identify and address these risks early. This process ensures compliance, minimizes surprises, and helps both parties navigate the transaction with greater confidence and transparency.

How do tax attributes like net operating losses (NOLs) and tax credits impact the value of an M&A transaction?

Tax attributes such as net operating losses (NOLs) and tax credits can play a big role in shaping the financial value of a merger or acquisition. These attributes can lead to future tax savings, making the deal more financially attractive. For example, NOLs can be applied to offset taxable income, effectively lowering the acquiring company’s tax bill. Similarly, tax credits can directly reduce future tax liabilities, adding to the transaction’s financial upside.

That said, these benefits don’t come without restrictions. In the U.S., regulations like Section 382 can limit how NOLs and tax credits are used after a change in ownership, which might diminish their overall value. Because of this, it’s crucial to thoroughly assess these tax attributes during the due diligence phase. This ensures the valuation is accurate and that the deal complies with tax laws.

How can potential tax liabilities uncovered during M&A due diligence be effectively managed?

Managing tax liabilities that come up during M&A due diligence calls for a well-thought-out, proactive plan. The first step? Conduct a comprehensive review of the target company’s tax history – this includes diving into past filings, compliance records, and any unresolved tax disputes. This early analysis helps pinpoint risks and potential opportunities.

From there, craft a post-transaction tax plan aimed at addressing any liabilities uncovered. This might involve restructuring deal terms or negotiating indemnities to safeguard against future surprises. Be sure to document everything thoroughly and put systems in place for ongoing monitoring. These measures not only streamline the integration process but also help minimize the chance of unexpected tax issues after the acquisition.

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