​Businesses and individuals facing complex tax issues with the Internal Revenue Service require more than technical compliance—they need strategic judgment.

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Our tax practice focuses on high-stakes matters involving IRS disputes, advance certainty, and risk management. We represent clients in IRS Appeals, advise on Private Letter Rulings (PLRs), and negotiate Advance Pricing Agreements (APAs) to resolve uncertainty and avoid future controversy.

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Early positioning in these matters can materially affect outcomes.

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IRS Appeals Representation

 

An IRS audit is not the end of the process. In many cases, the most important decisions happen after the examination phase—when a case moves to Appeals.

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We represent clients before IRS Appeals in disputes involving:

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• Income tax adjustments

• Transfer pricing issues

• Penalty assessments

• Complex factual and legal determinations

 

IRS Appeals evaluates cases based on the hazards of litigation, creating opportunities for resolution that are not available during audit.

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When IRS Appeals May Be the Right Strategy

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• The legal issues are subject to interpretation

• There is uncertainty in how a court would rule

• A negotiated resolution is preferable to litigation

 

Strategic Considerations

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Entering Appeals too early—or without a developed record—can reduce leverage. We work with clients to ensure that positions are properly framed before engaging in the Appeals process.

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Learn more about our IRS Appeals attorney services.

 

Private Letter Ruling (PLR) Requests

 

A Private Letter Ruling provides formal guidance from the IRS on the tax treatment of a specific transaction. In situations involving uncertainty, a PLR can eliminate risk before positions are taken on a return.

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We advise clients on whether a PLR is appropriate and prepare ruling requests involving:

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• Corporate transactions

• Partnership structures

• International tax issues

• Novel or unclear tax positions

 

When a PLR Makes Sense

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• The tax treatment is uncertain and material

• The transaction cannot be easily reversed

• Audit risk would be costly or disruptive 

 

Cost and Timing

 

PLRs involve IRS user fees and require detailed submissions. In some cases, the cost and timeline outweigh the benefit. We help clients evaluate whether a ruling is the most effective path—or whether alternative strategies are preferable.

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Learn more about Private Letter Ruling requests.

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Advance Pricing Agreements (APAs)

 

An Advance Pricing Agreement allows taxpayers to proactively resolve transfer pricing issues with the IRS before they become disputes.

 

We represent clients in negotiating APAs involving:

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• Intercompany pricing arrangements

• Cross-border transactions

• Transfer pricing methodologies

 

Benefits of an APA

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• Reduces audit risk

• Provides certainty over multiple tax years

• Avoids prolonged disputes with tax authorities

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When an APA Is Worth Considering

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• Transfer pricing positions are material

• The risk of audit is high

• Long-term certainty is more valuable than short-term flexibility

 

APAs are not appropriate in every case. We help clients assess whether the upfront investment is justified based on their specific risk profile.  

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Learn more about Advance Pricing Agreements.

 

Integrated Tax Controversy Strategy

 

These processes—Appeals, PLRs, and APAs—are not isolated tools. They are part of a broader strategy for managing tax risk.

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We advise clients on:

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• Whether to resolve issues administratively or prepare for litigation

• When to seek advance certainty versus defending a position

• How to align tax positions with long-term business objectives

 

In high-value matters, the difference between a reactive and proactive approach can be substantial.

 

Who We Represent

 

Our clients include:

 

• Closely held and middle-market businesses

• Multinational companies

• High-net-worth individuals

• Tax directors and in-house counsel

 

Practical, Strategic Guidance

 

Tax controversy is not just about technical correctness—it is about positioning, timing, and judgment.

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Whether addressing an ongoing dispute or evaluating a potential issue before it arises, we provide strategic guidance designed to protect our clients’ interests and reduce uncertainty.

 

Next Steps

 

If you are facing an IRS dispute or considering a Private Letter Ruling or Advance Pricing Agreement, early evaluation can materially affect the outcome.  Contact Zion Levi, Esq. today to discuss your situation and next steps.  

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