It might seem odd, but it is possible to get the IRS to give you a straight-forward and binding answer to ambiguous tax positions in advance. How does this happen, you ask? The answer is through an IRS private letter ruling.

IRS private letter rulings provide many benefits, but they are not easy to obtain. There are costs, potential delays, and even then, you run the risk of not being granted a ruling. This dynamic might seem odd as the entire point of applying for a private letter ruling is to obtain certainty. If your position is weak from a tax law perspective, the government could refuse to rule on it. Alternatively, if the position you are seeking is obviously correct, the government might refuse to rule as well because they don’t like to issue “comfort rulings.” Essentially, the only way to get the government to rule is to make a request regarding a position that is in the middle.

If you believe the tax position in question lies somewhere in the middle, requesting a private letter ruling may make sense. If you are more likely one of the outliers, then requesting a tax opinion usually makes more sense. The problem is that tax opinion, unlike private letter rulings, doesn’t bind the IRS.

Deciding Which Path to Take

If the relative certainty of the tax position in question doesn’t provide enough guidance, how do you decide to go after a tax opinion versus a private letter ruling? To make the choice, it helps to understand more details.

First, tax opinions can cover a broader range of topics and can be written about pretty much anything; rulings cannot. In fact, the IRS has an explicit list of subjects that it will not produce private letter rulings on (they modify it occasionally, but there’s always a list). As a result, the first step is to assess the list as this might make the choice for you.

Second, don’t request a private letter ruling unless there is a good chance you think it will be granted. For one, rulings are not cheap with fees often costing upward of $25,000 to obtain a ruling. If you get a “No” ruling against your position, you can withdraw the request to take the ruling off the books, but you may or may not get the fee back. Moreover, when you withdraw a request for a ruling, the IRS sends a notice to your local IRS field office, potentially flagging your return for audit.

Third, opinions can be quick and obtained in as little as a few days or weeks. Rulings, on the other hand, often take months. Also consider that a request for a ruling must be specific and there is little room for modification after filing. Opinions have more flexibility.

Private Letter Ruling Process

Given the specificity and consequence of requesting a ruling, there are intermediate steps to help you test the water before you go all in. Nearly all ruling requests start by initiating a discussion with the IRS to get their general view on your proposed ruling. After this, the taxpayer usually submits a brief memo covering the facts and ruling they are looking to obtain. Next, there are more meetings either in person or by phone with IRS attorneys involved. At this point, if everything looks good, you can prepare and submit the actual ruling request. If you back out at this point, you avoid triggering any fees (IRS fees – not your lawyers or accountants) or audit notices.

Benefits of a Ruling Versus an Opinion

The reason taxpayers go through the time, expense and effort to obtain rulings instead of opinions is that they have several advantages. First, rulings are binding on the IRS. Second, you don’t need to consider penalty protection. Most of all, they provide certainty. Given the difficulty in obtaining a ruling, they generally make financial sense only when a taxpayer has a seriously substantial tax position in play, or at least will over time, and he wants to protect against future audits and legal challenges.

Coming out on the winning side of a lawsuit as a plaintiff can be a gratifying feeling, especially if there is a financial settlement involved. There is likely a sense of both relief and vindication. Unfortunately, far too often people are in for a shock when they realize that they must pay taxes on the award. You can even be taxed on your attorney fees! However, a little tax planning can go a long way, especially if you do it before the settlement is finalized and the award is substantial. Below are the five key rules to know so you can make the right move.

1. The Origin of the Claim Largely Determines the Tax Consequences
   The taxation of legal settlements is based on the origin or reason of the claim. For example, if you win a wrongful termination suit against an employer, your award will be taxed as both wages and likely some other income for whatever is allocated to emotional damages. On the other hand, if you sue the contractor who built your house for damage caused by his negligence, the settlement might not be deemed income at all and you could treat it as a reduction of the purchase price of the real asset. There are many exceptions in this area, and it always depends on the facts and circumstances of the case.
2. Physical Injuries Produce Tax-Free Awards, but Emotional Distress and Damages Are Taxable
   Damages received for suits involving a physical injury or illness are tax-free. Suits for emotional distress and defamation are taxable, including the physical symptoms of emotional distress (gastrointestinal problems, etc.). Be careful as the latter can be ambiguous, so agreeing on the nature of a physical symptom as the cause or result of emotional distress is best done with the defendant before you finalize the case.
3. Allocating Damages
   Legal disputes typically involve several issues and courses of conduct. As a result, settlements typically have multiple types of consideration, each with potentially different tax treatments. If the plaintiff and defendant both agree on the tax treatment before finalizing the case, then you can allocate the total damages to certain categories and save taxes. Such agreements are technically non-binding on the IRS, but they are rarely challenged.
4. Attorney Fees 
   Plaintiffs who use a contingent fee lawyer are typically taxed on receiving 100 percent of the money recovered. This means you have to pay taxes even on the portion of your settlement that the lawyers keep as their fee. This is still the case even if your contingent fees are paid directly by the defendant. In clear cases of physical injury where the entire settlement is non-taxable, there’s no issue – but if your award is taxable, you’ll need to be careful.

   Take an example where you collect a contingent fee settlement for emotional distress and receive $200,000, with your lawyer taking 30 percent or $60,000. In this case, you’ll typically be liable for taxes on the entire $200,000 and not just the $140,000 you keep. To make matters worse, aside from legal fees in employment and certain whistleblower claims, there’s no corresponding deduction for legal fees. There are potential ways to mitigate this, but tax advice early in the process is key.

5. Punitive Damages and Interest
   Generally, punitive damages and interest are always taxable. For example, take a case where you are hurt in an automobile crash and receive $100,000 in compensatory damages and another $3 million in punitive damages. The $100,000 is tax-free, whereas the $3 million is taxable.

   Interest is treated similarly. Even if you receive a tax-free type of settlement, but it took time to finalize the settlement through the pre- or post-judgment process, the interest you receive is taxable. Therefore, it is often advantageous to settle a case instead of having it go to judgment.

Conclusion

The taxation of legal settlements and awards are nuanced and largely depend on the facts and circumstances of the case at hand. There are, however, many opportunities through proper tax planning to minimize the tax consequences, but only if you are proactive and plan early in the process.