Tax Planning for Retirees


The 60-day rollover rule: Self-certifying waiver eligibility, TAX ADVISER, Jan. 2018, at page 38. Explains how a taxpayer may self-certify that he or she has permissible reasons for failing to roll over retirement funds within the required 60-day period after distribution of the funds.

Rollovers to Roth IRAs Are Complicated by Substance-over-Form Doctrines,  TAXES, Sep. 2015, at page 43; 3 CCH FINANCIAL AND ESTATE PLANNING ¶ 34,071 (2016).  Analyzes application of the step transaction doctrine to certain rollovers to Roth IRA.

Distributions to Beneficiaries of Tax-Favored Retirement Plans, Before  and After the SECURE Act, TAX LAWYER, Fall 2020, at page 43.  Explains how the SECURE Act of 2019 changes the tax treatment of beneficiaries of tax-favored retirement plans.

The SECURE Act: Retirement Plan Distributions After the Death of a Beneficiary, TAX LAWYER, Summer 2021, at page 629.  Explains how the SECURE Act of 2019 changes the tax treatment of distributions from a tax-favored retirement plan after the death of a beneficiary.

Correcting excess contributions to IRAs, TAX ADVISER, Apr. 2020, at page 252. Explains the various methods for wholly or partially curing excess contributions to IRAs, to avoid the six percent excise tax on such contributions.

IRA Rollovers to Qualified Plans: The Retained Investment Issue,  TAX NOTES, Sep. 18, 2017, at page 1571.  Analyzes the treatment of the earnings and investment portions of an IRA distribution that is partly rolled over to a qualified plan, a rollover with consequences often misunderstood.

Qualified Equity Grants: Tax Deferral for Illiquid Employer Stock, JOURNAL OF TAXATION, Oct. 2018, at page 6. Discusses qualified equity grants, grants that allow the deferral of compensation on the exercise of stock options and on the settlement of restricted stock units. Such grants are particularly useful for the deferral of tax on illiquid non-publicly-traded employer stock.

Retiree Tax Planning with Qualified Longevity Annuity Contracts,  TAX ADVISER, Nov. 2014, at page 822. Explains the use of qualified longevity annuity contracts (QLACs) to lengthen retirement payouts and tax deferrals for IRAs and other retirement plans.

Using DISCs to Avoid Roth IRA Limits: An Overlooked Fact in Summa,  TAX NOTES, Nov. 13, 2017, at page 973.  Discusses the Sixth Circuit Summa case, holding that a DISC may be used to circumvent Roth IRA contribution limits. However, because of an overlooked fact, other circuits may decline to follow Summa on similar facts.

Controlling and Minimizing the Taxation of Disability Benefits,  TAX LAWYER, Spring 2007, at page 725. Discusses tax planning for disability benefits, including employee disability, workers compensation, and benefits for loss of bodily function, military combat and terrorist-related injuries, and other wrongful injuries or sickness.

Retirement Plans, IRAs, and Annuities: Avoiding the Early Distribution Penalty,  TAX ADVISER, Apr. 2011, at page 254.  Explains the many exceptions that may allow early distributions from annuities, IRAs, and other retirement plans without imposition of the usual 10 percent penalty on early distributions.

Required Spousal Annuities Under Qualified Retirement Plans,  TAX NOTES, Nov. 19, 2007, at page 783.  Explains how to navigate the rules applicable to spousal qualified joint and survivor annuities (QJSAs), qualified preretirement survivor annuities (QPSAs), and waivers of those annuities.

Retiree Tax Planning for Eligible Retirement Plans of Tax-Exempt Entities,  TAX ADVISER, Jan. 2012, at page 24.  Explains tax planning for unfunded eligible plans, including sophisticated distribution elections tailored to the needs and goals of retirees.

Planning Lump Sum Distributions of Employer Stock from Stock Bonus Plans and ESOPs,  TAXES, Nov. 2015, at page 49.  Discusses the feasibility of deferring all the tax on a lump sum distribution of employer securities, by rolling over securities with a value equal to the otherwise taxable portion of the distribution and personally retaining the remainder of the securities (carrying the net unrealized appreciation (NUA)).

Retirement Planning for Unfunded Deferred Pay Under Section 409A,  PRACTICAL TAX STRATEGIES, July 2008, at page 14.  Discusses how to avoid the severe penalties that may be imposed on participants in nonqualified deferred compensation plans.

Divorce, QDRO, Retirement, Death: Not Necessarily in That Order,  TAX NOTES, Apr. 29, 2019, at page 707.  Discusses the effect of retirement and death on the ability to obtain qualified domestic relations orders (QDROs).

Deferred Compensation: The Proposed Sec. 457(f) Regulations and Sec. 409A, TAX ADVISER, June 2017, at page 422. Explains the proposed Sec. 457(f) regulations and their interaction with Sec. 409A.

Tax Issues Complicate the Costs of Chronic Illness and Long-Term Care Insurance,  JOURNAL OF TAXATION, Apr. 2007, at page 216.  Discusses tax and insurance planning for chronic and terminal illnesses of the elderly, including the treatment of viatical settlements.

Retirement Tax Planning With Personally Purchased Annuities,  TAX NOTES, Oct. 30, 2006, at page 459.  Explains the taxation of annuities that are directly purchased by a retiree from an insurer, including the significant differences between the treatment of annuities purchased before June 30, 1986 and those purchased after that date.

Sec. 403(b) retirement plans: A comparison with 401(k) plans, TAX ADVISER, Jan. 2021, at page 30. Compares 403(b) retirement plans with 401(k) plans from the standpoint of a plan participant.

Sec. 457 government plan distributions compared to 401(k) distributions, TAX ADVISER, Feb. 2021, at page 116. Compares 457 government plans with 401(k) plans from the standpoint of a plan participant.

IRA and Retirement Plan Rollovers: IRS Waivers of the 60-Day Rollover Period,  JOURNAL OF RETIREMENT PLANNING, Sep.-Oct. 2005, at page 17.  Explains when and why the IRS will, or will not, waive a failure to timely roll over distributions from an IRA or retirement plan.

Maximizing Medical Deductions for Residents of Retirement Communities,  JOURNAL OF TAXATION, Jan. 2007, at page 50.  Explains how to maximize deductions for the medical expense portions of payments to continuing care retirement communities (CCRCs).

Determining Taxpayer Investment in Retirement Plans and IRAs,  JOURNAL OF RETIREMENT PLANNING, Mar.-Apr. 2006, at page 17.  Explains how the annuity contract rules apply in determining investment (basis) in the funds and distributions of IRAs and other retirement plans.

If and when to borrow from a qualified retirement plan, TAX ADVISER, July 2018, at page 436. Explains how to choose between borrowing from a qualified retirement plan or from an outside lender.

Birth or Adoption Exception to the Early Retirement Distribution Penalty,  TAX NOTES, June 7, 2021, at page 1541.  Explores the requirements and consequences of the birth or adoption exception to the ten percent penalty on early distributions from tax-favored retirement plans.

Annuity and Life Insurance Contracts Purchased by Trusts Under Qualified Retirement Plans,  JOURNAL OF RETIREMENT PLANNING, July-Aug. 2006, at page 11.  Explains the tax treatment of (1) the cost of life insurance policies purchased by retirement plans, (2) the death benefits from the policies, and (3) plan distributions of transferable and nontransferable policies.

The Taxation of Reverse Mortgages,  JOURNAL OF FINANCIAL PLANNING, (Internet edition), Aug. 2010.  Explains how the tax law applies to reverse mortgages, including particularly the tax treatment of interest payments, points, insurance premiums, and gain or loss on termination of the mortgage.

Articles Substantially Superseded by Subsequent Developments

Conversions to Roth IRAs and Roth Recharacterizations, JOURNAL OF RETIREMENT PLANNING, Nov.-Dec. 2005, at page 11.  (See instead Chapter 6 of the treatise.)

Maximizing Tax Deferral for Funds in Tax-Favored Retirement Plans and IRAs, 3 CCH FINANCIAL AND ESTATE PLANNING ¶ 32,871 (2006); JOURNAL OF RETIREMENT PLANNING, Jan.-Feb. 2006 at page 15.  (See instead Chapter 8 of the treatise.)

Retirement Plans and IRAs: Rollovers of Taxpayer Investment, JOURNAL OF RETIREMENT PLANNING, May-June 2006, at page 29.  (See instead Chapter 2 and Chapter 5 of the treatise.)

Retiree Tax Planning for Designated Roth Accounts, PRACTICAL TAX STRATEGIES, Mar. 2011, at page 100. See instead Chapter 7 of the treatise.)

Planning Now for the New Tax on Retiree Net Investment Income, 3 CCH FINANCIAL AND ESTATE PLANNING ¶ 33,461 (2011); JOURNAL OF RETIREMENT PLANNING, Nov.-Dec. 2010 at page 11.  (See instead Chapter 19 of the treatise.)