Tax-Loss Harvesting Part II: The Wash Sales Rule Forum

SEPTEMBER 24, 2026, CHICAGO – The firm is pleased to announce that Mark S. Perwien has joined the firm as Of Counsel, continuing his illustrious career in private practice after his work in government and on Wall Street. Perwien has focused on the overlap of taxation and derivatives law for more than 40 years. He began his career at Salomon Brothers, remaining with that firm and its successors for 20 years through various management roles to ultimately assume tax department leadership at Citigroup. Perwien left Citi to assume similar high-level roles at Goldman Sachs where he led activities at the derivatives desk and the tax department. Perwien went on to join the Internal Revenue Service (IRS) where he served as Special Counsel, Office of the Associate Chief Counsel, Financial Institutions and Products in Washington; and as Senior Advisor, Financial Products, to the Director of Enterprise Activities, Large Business and International Division in New York for more than a decade. “ASKramer Law addresses some of the most complex and challenging tax and regulatory questions in financial law today. My focus has always been to consider these questions in practical ways that comply with the law, and withstand scrutiny in this fast-changing regulatory landscape,” Perwien said. “Today, digital asset market innovators are reshaping brokerage, banking, and exchange operations as we know them, so it is an exciting time to be working in the world of derivatives. An association with Andie

‍ ‍ June 15, 2026, CHICAGO – The firm is pleased to announce that Andrea (Andie) S. Kramer has been recognized as a top tax and derivatives lawyer in Chambers USA and The Legal 500 US. Kramer has focused her practice on taxation and derivatives law for more than 30 years. In 2026, her Chambers U.S. rankings sustained at ‘Band 1’ for Tax, and rose to ‘Band 2’ for Derivatives, USA - Nationwide; and to ‘Band 3’ for Derivatives in the Chambers Global Guide. In addition to retaining her ‘Hall of Fame’ status in Financial Products Taxation in The Legal 500 US, Kramer also joins their ‘Hall of Fame’ for her longstanding work in Derivatives. “I am truly honored to receive these recognitions,” Kramer said. “They confirm that hard work, a focus on your clients, and a commitment to the legal profession really pays off. I believe that awards like these can encourage young lawyers who work long hours, balance family and caregiving demands, while giving back to the profession and their communities. I say to them: Keep at it. Your day will come.” We would like to thank many clients and colleagues for participating in this important research. It takes real effort to provide feedback, and we understand that time is at a premium. Every day, we do our best to provide carefully considered legal counsel and deliver strong client service, while giving back to the profession and sustaining our civic commitments. This year, especially, we truly appreciate the recognition of these efforts. About ASKr

By Nicholas C. Mowbray, Andrea S. Kramer, and Stephen Roman In this article, Nicholas C. Mowbray, Andrea S. Kramer, and Stephen Roman continue their review of regulated investment companies (“RICs”) from “Types of Regulated Investment Companies and Exchange-Traded Funds: Part I”. Read Full Article Disclaimer This article contains general information and is not intended to serve as, and should not be taken to be, legal advice for any purpose. No reader should act or refrain from acting on the basis of information in this article, and before acting or not acting with respect to any matter addressed in this article readers should seek legal advice from counsel in the relevant jurisdiction. ASKramer Law LLC expressly disclaims any liability with respect to actions taken or not taken based on the content of this article. This material may be construed as attorney advertising. ASKramer Law LLC’s founding member, Andie Kramer, focuses her practice on legal issues that arise in connection with financial products, energy, and digital assets. She is co-author of Financial Products: Taxation, Regulation, and Design (with the copyright held by CCH Incorporated and its affiliates), a treatise that is updated annually. She is co-author of Energy and Environmental Project Finance Law and Taxation: New Investment Techniques (with the copyright held by Matthew Bender®), a hands-on guide for energy project developers and their advisors, which is also updated annually. In addition, she regularl

By Nicholas C. Mowbray, Andrea S. Kramer, and Stephen Roman In this article, Nicholas C. Mowbray, Andrea S. Kramer, and Stephen Roman explain and review Regulated investment companies (“RICs”). Read Full Article Here Disclaimer This article contains general information and is not intended to serve as, and should not be taken to be, legal advice for any purpose. No reader should act or refrain from acting on the basis of information in this article, and before acting or not acting with respect to any matter addressed in this article readers should seek legal advice from counsel in the relevant jurisdiction. ASKramer Law LLC expressly disclaims any liability with respect to actions taken or not taken based on the content of this article. This material may be construed as attorney advertising. ASKramer Law LLC’s founding member, Andie Kramer, focuses her practice on legal issues that arise in connection with financial products, energy, and digital assets. She is co-author of Financial Products: Taxation, Regulation, and Design (with the copyright held by CCH Incorporated and its affiliates), a treatise that is updated annually. She is co-author of Energy and Environmental Project Finance Law and Taxation: New Investment Techniques (with the copyright held by Matthew Bender®), a hands-on guide for energy project developers and their advisors, which is also updated annually. In addition, she regularly addresses related topical issues in articles posted on www.askramerlaw.com and e

April 2, 2026 ‍In Part I: Welcome To The Crypto Zone, [1] Where Are We? I reviewed the global crypto [2] landscape where people engage in a wide range of digital asset transactions and activities. In Part II: What Can We Find Here? I focused on digital asset definitions, tax character, and what types of crypto-related income streams and related expenses U.S. taxpayers need to determine when reporting certain crypto transactions. Here in Part III: How Do We Get Out? we’ll focus on digital asset tax return filing requirements. And yes, you’ve guessed it . . . the only way to get out of The Crypto Zone is to file! We will start this final part of this Q&A with Andie , by looking at the “digital asset question” that is now included on most U.S. federal income tax returns. I will touch on the fundamentals of calculating tax basis, mention some state and local filing obligations, and conclude with a quick look at some of the resources that can help you meet your compliance obligations. This part of the series also updates my 2023 article, Tax Return Reporting of Cryptocurrency. [3] How has “the digital asset question” changed in recent years? “The digital asset question” now appears on many federal income tax returns. It was first added to individual and senior income tax returns in 2019, but this question has evolved and changed over time. Taxpayers must answer the digital asset question and report all digital asset-related income when they file their returns. The 2025 digital ass

March 31, 2026 We began this series with Part I:Where Are We? by reviewing the background, developments, and implications of current global and national regulatory and tax frameworks for digital assets. In Part II: What Can We Find Here? I look at what taxpayers can find as they consider the types of income they receive from crypto [1] activities. In Part III How Do We Get Out? I will address how U.S. taxpayers figure out tax basis and ways to better understand their 2025 tax return filing obligations. Here in Part II, I take U.S. taxpayers through what —precisely—might qualify as a digital asset. Next, I look at how the IRS defines and taxes digital assets. And then I review some likely sources of crypto-related income and compensation U.S. taxpayers could receive as a result of their activities in the Crypto Zone. [2] Together, we look at some of the IRS 1099 forms that payors use to report various payments made to taxpayers showing income streams from sources other than employment. I go into the reasons taxpayers may want to carefully review the 1099s they receive for the past tax year. This review can be helpful for taxpayers when organizing their crypto activities, since they line up with 1099s they received that relate to direct crypto transactions; crypto earnings and compensation received from crypto-related activities; and trading and investment activities. Later in the article, we will go through some of the crypto areas that some of the more popular 1099s cover. Bu

March 20, 2026 Do you invest in crypto, [1] buy and sell cryptocurrencies, dabble in crypto derivatives, or invest in Crypto ETFs? [2] Are you an active miner or staker earning rewards as you help grow the blockchain? Perhaps you hold equity in companies building future crypto products, technologies, and infrastructure. Or maybe you enjoy exploring many of the dimensions of crypto. Welcome to The Crypto Zone. [3] In this new three-part series, Welcome to The Crypto Zone , we look at the where, what, and how of crypto taxation for U.S. taxpayers. In Part I: Where Are We? I take you through the global crypto tax environment and explain why the U.S. government is focusing on digital asset taxation and information reporting. I explain why the obligations to report global crypto income of U.S. taxpayers don’t begin and end with those new 1099-DA forms. I look at jurisdictional questions that can arise when crypto transactions take place on global blockchains, some national and international regulatory and enforcement developments, and related implications for privacy rights. And I address why U.S. taxpayers need to properly report their crypto income whether it is derived at home or abroad. In Part II: What Can We Find Here? We look at the definition and tax character of crypto; along with providing a high-level overview of what information U.S. taxpayers need to accumulate and review to determine their crypto tax obligations. I offer a quick overview of obligations for taxpayers

By Andrea S. Kramer and Samuel G. Kramer In this article, Andie Kramer and Samuel Kramer explore what we understand money to be from various laws, regulations, and regulatory guidance to help understand what money is, how it functions in our financial system, and whether cryptocurrency should be treated as money or something else entirely. Read Full Article Disclaimer This article contains general information and is not intended to serve as, and should not be taken to be, legal advice for any purpose. No reader should act or refrain from acting on the basis of information in this article, and before acting or not acting with respect to any matter addressed in this article readers should seek legal advice from counsel in the relevant jurisdiction. ASKramer Law LLC expressly disclaims any liability with respect to actions taken or not taken based on the content of this article. This material may be construed as attorney advertising. ASKramer Law LLC’s founding member, Andie Kramer, focuses her practice on legal issues that arise in connection with financial products, energy, and digital assets. She is co-author of Financial Products: Taxation, Regulation, and Design (with the copyright held by CCH Incorporated and its affiliates), a treatise that is updated annually. She is co-author of Energy and Environmental Project Finance Law and Taxation: New Investment Techniques (with the copyright held by Matthew Bender®), a hands-on guide for energy project developers and their adviso

January 29, 2026 “De minimis” has gotten a lot of airplay in discussions about the regulation and taxation of crypto. [1] De minimis comes from the Latin maxim, "de minimis non curat lex," translating to "the law does not concern itself with trifles." Much U.S. law is rooted in Early English common law, and by extension, Roman law with all its Latin vernacular. [2] According to Wex, [3] “De minimis is something that is very trifling or of little importance. [It] usually refers to something so small, whether in dollar terms, importance, or severity, that the law will not consider it.” Concerning trifles The de minimis doctrine seeks to keep trivial matters from clogging up the court system; it keeps a party from bringing up unrelated, insignificant things; it results in the dismissal of some lawsuits; [4] and it can help a taxpayer to avoid the burden of reporting and paying taxes on tiny monetary amounts. De minimis has been applied to many areas of U.S. regulation and taxation. De minimis tax exceptions and exclusions range, for example, from tiny wage claims, to fringe benefits, to capital gains on certain profits when bonds reach maturation, to taxation on the personal use of foreign currency. In determining whether a situation meets the definition of de minimis, legal systems, regulators and courts consider (1) whether the related time and tasks can be accurately captured and recorded; (2) the monies involved; (3) whether work performed is irregular or scheduled; [5] and

December 30, 2025 Crypto [1] is an extraordinary growth market with profound implications for foreign investment in the United States. The current U.S. administration has made a clear, specific, and demonstrable commitment toward development of crypto during 2025. And there is no subject that is more important in encouraging U.S. crypto market expansion than the tax framework that is needed to ensure safe harbors for foreign investment. Safe harbors are intended to provide foreign investors with certainty as to the statutory interpretation, avoid confusion, and ensure that they do not inadvertently find themselves in a U.S. trade or business. Code [2] Section 864(b)(2) [3] provides trading safe harbors for securities and commodities. They were enacted to encourage foreign investment in the United States through a resident U.S. broker, commission agent, custodian, or other independent agent trading on behalf of non-U.S. investors. At present, there is one safe harbor for stock and securities, and another for commodities. The Securities Safe Harbor applies to stock and securities, with securities defined as “any note, bond, debenture, or other evidence of indebtedness,” and “any evidence of an interest in or right to subscribe to or repurchase any of the items listed above.” [4] The Commodity Safe Harbor defines “commodities” more narrowly by limiting the definition to commodities that are “of a kind” “customarily dealt in” on an “organized commodity exchange” provided the tran

December 30, 2025 The U. S. Congress is reviewing the regulatory framework for the taxation of digital assets at the time of this writing. At the president’s direction, [1] rules that affect digital asset taxation have been a focus of both the House of Representatives and the Senate. [2] In particular, since the House passed the CLARITY Act (pending in the Senate) and the report of the President’s Working Group on Digital Asset Markets was issued in July 2025, [3] a number of Congressional Committees have been reviewing existing and proposed digital asset taxation in some detail. I have been involved with these efforts as an invited witness, providing testimony before the Senate Committee on Finance in October, [4] and offering my feedback in various follow-up communications with governmental leaders. This month, Representative Steven Horsford (D-NV) and Representative Max Miller (R-OH) released a new discussion draft of The Digital Asset Protection, Accountability, Regulation, Innovation, Taxation, and Yields (PARITY) Act (Draft Bill). [5] It addresses some of the issues under review in this series, including anti-abuse rules. Anti-abuse rules are important in tax law. They are designed to prevent bad actors from exploiting “tax loopholes” and thereby avoid paying taxes that they would otherwise owe. As I note in my book, “although clear in principle, this area can get murky when some economics may exist and the motivation of the taxpayer is unclear.” [6] In these markets, w

December 30, 2025 Some crypto [1] products are taxed as securities and some are taxed as actively traded commodities. These products are allowed to elect into mark-to-market under current law. Because there is ambiguity with respect to which digital assets are commodities, which are securities, and what is meant by “actively traded,” dealers and traders in digital assets have requested clarity as to when they can use the mark-to-market method of tax accounting with their specific crypto holdings. Mark-to-market tax accounting is a valuation method for assets and liabilities based on what they could be bought or sold for in today's marketplace rather than at their original purchase price. This approach gives a real-time snapshot of financial worth on a given day. [2] The chosen day for such a snapshot to be taken is the last business day of the taxable year, when the taxpayer’s asset must be treated as if it were sold for its fair market value, and appropriate gains and losses are recognized, regardless of whether the underlying asset is sold. Multiple sections of the Internal Revenue Code (Code) [3] have allowed or required mark-to-market accounting for decades—and the method is a well-established under both Code Section 475 and Code Section 1256. Let’s take a look at both sections and consider the related overview, along with the (potential) application of the mark-to-market accounting method for digital assets. Covered Products Mark-to-market tax accounting is mandatory for