An IRA to Roth IRA conversion can be a smart move that can help you keep more of your money in retirement. In this article, I’ll explain what a Roth IRA Conversion is, why it can be powerful for high earners, and how it compares to traditional saving. We’ll also look at how this strategy works for a couple nearing retirement, and how it can help them avoid higher taxes and Medicare surcharges later in life. In fact, retirement accounts that have embedded taxes to be paid overstate how much you will get to spend. I wrote this article about…

The Internal Revenue Service (IRS) has a long-standing reputation in the US that is largely negative in nature. A simple internet search of the “IRS reputation” results in articles logging the challenges with timely processing and concerns with the quality of support provided by the agency. These issues, among others, have led many legislators and lobbyists to call for an overhaul of the organization. The Trump Administration has echoed these sentiments and recently initiated efforts to shrink the IRS with a reduction in existing staff and a hiring freeze on new staff. Reports indicate their target is to reduce the…

The Department of Government Efficiency (DOGE) team reportedly wants to use information from the IRS to investigate potential fraud in the Supplemental Nutrition Assistance Program (SNAP, formerly food stamps). Disclosure restrictions may prevent IRS from sharing the data. But prior analysis at the Urban Institute focused on improving tax administration shows that even if IRS did share the data, differences between how taxes and SNAP are administered likely make the data of limited value. Income standards don’t align SNAP benefits are based on monthly family income, which SNAP can already verify using an electronic tool called “The Work Number” .…

The early months of the year are important for taxpayers ages 70½ and older who have traditional IRAs. The right plan developed early in the year can reduce taxes on required minimum distributions this year and for years to come. Not planning, or waiting until later in the year, can mean lost opportunities and routinely costs taxpayers a bundle. Traditional IRA owners ages 70½ and older have available to them one of the most powerful tax and charitable-giving tools, the qualified charitable distribution. RMDs bedevil many traditional IRA owners as they age. The rules force them to take distributions from…

IRS data from the seventh week of the tax filing season—the week ending March 14, 2025—indicates that taxpayers are not excited about filing this tax season. Numbers for tax filing and processing of tax returns dipped again, a trend that hasn’t changed since the season opened on January 27, 2025. Filing and Processing Dips Early filing data reflects a continued downturn in tax returns received compared to the prior year. The data shows that the IRS received 70,370,000 individual income tax returns as of March 14, 2025, compared to 71,587,000 as of March 15, 2024. The dip is 1.7%, with…

A day after Frank Bisignano, President Donald Trump’s nominee to lead the Social Security Administration (SSA), told the Senate Finance Committee that phone service was “a part of meeting beneficiaries where they want to get met,” the agency apparently took their likely future boss at his word. Today, the Social Security Administration changed course on its online-centric service policy, committing to phone service for certain beneficiaries. Calling the measures “proactive steps to enhance the security of its services by implementing stronger identity verification procedures,” the agency announced that beginning April 14, 2025, individuals applying for Social Security Disability Insurance (SSDI),…

It’s a tax nerd’s fever dream—a value added tax case against tech giants that leans into barter theory and challenges the “free” (as in beer) in free platforms. According to Reuters, in a recent levy, Italy has told Meta, X and Microsoft that if it walks like a transaction and quacks like a transaction, it’s getting taxed like a transaction. There is no such thing as a free lunch—or, apparently, a free Facebook account in Italy. That’s the general thrust of the argument Italian tax authorities seem to be advancing in a landmark VAT case against big tech. The theory…

Tax season is in full swing, and if you’ve touched crypto—whether through buying, selling, staking, or trading NFTs—you need to know: the IRS is watching. In recent years, the Internal Revenue Service (IRS) has increased its scrutiny of digital asset activity. It classifies cryptocurrencies and other digital assets, including non-fungible tokens (NFTs), as property—not currency—for tax purposes. This distinction carries significant implications: property is subject to capital gains taxation when sold or exchanged, unlike traditional currencies. So even though “currency” is in the name, crypto is treated more like stocks or real estate than dollars or euros in the eyes…

With the filing deadline for tax returns less than a month way, taxes and the IRS are probably on your mind. Although levels of tax-related anxiety vary by person, it’s safe to say that everyone fears unwanted IRS attention, especially an audit. Despite layoffs at the IRS and aspirational talk from some quarters about replacing income taxes with tariffs, the IRS and its audits are not going anywhere. It is wishful thinking to believe that the federal government—even after the department, agency, and workforce cuts being made by President Donald Trump—could ever afford to eliminate the IRS and the tax…

The IRS taxes most lawsuit settlements, and exact wording matters if you are trying to avoid that grim result. However, some settlements can be positioned as capital gain. Here are a few examples: A suit about intellectual property; A founder dispute about shares in a company; A landlord tenant dispute with a lease buyout; A suit about damage to or conversion of property; A suit about construction defects, harm to property or diminution in its value; A suit against an investment adviser for losing your money; A lemon law suit about a defective vehicle; Lower Tax Rates and Recouping Your…