deepdive.

The October 15, 2026 deadline is approaching for extended 2025 tax returns. Learn why early filing and complete documents matter.

Learn how life insurance can affect taxes, including cash value growth, MEC rules, policy loans, life settlements, and accelerated death benefits.

As college athletic departments face rising costs and multimillion-dollar athlete payments, some states are using tax revenue and public funds to help schools compete. Here's what's changing.

A living inheritance can help children when they need it most, but large gifts can create tax and estate-planning consequences. Here’s what to consider before transferring wealth.

A new rule may let eligible taxpayers use retirement funds to pay qualified long-term care insurance premiums without the 10% early-withdrawal penalty.

Supporting children, helping aging parents, and protecting your own retirement can turn you into the family CFO. Here’s how to manage the financial overlap.

Business expenses can reduce taxable income, but many learn too late that a deduction is only as good as the records behind it.

Should you pay off debt or invest? Higher interest rates have shifted the balance. Learn how to evaluate high-interest debt, emergency savings, retirement planning, and taxes when making important financial decisions.

An executor of a decedent’s estate must administer the estate and distribute assets in the statutory order of priority; failure to follow those legal requirements can expose the executor to personal liability.

If you make or receive income that is not fully covered by withholding, September 15, 2026, is an important date on the tax calendar. It is the due date for the third installment of 2026 federal estimated tax payments for individuals who are not paying enough through withholding during the year. 

Your final decade before retirement can have the biggest impact on your financial future. Learn the key planning opportunities at ages 50, 55, and 60—and why proactive tax planning matters.

Donating long‑term appreciated stock (publicly traded shares held for more than one year) to a qualified charity is a high‑impact way for donors to support causes while obtaining favorable tax treatment.

If you inherited a Traditional IRA after 2019, the rules are not always what people expect. The SECURE Act changed the way many inherited retirement accounts must be paid out, and now who inherited the account and whether the original owner had already started required minimum distributions, or RMDs, controls. In some cases, a surviving spouse still has the most flexibility. In other cases, the money must come out within 10 years.

The holiday season starts earlier than many business owners realize. Discover seven proactive financial moves to strengthen cash flow, manage inventory, and optimize taxes before Q4.

As kids head back to school, give your business a mid-year report card. Discover seven key areas every small business owner should review before year-end.

Under the Internal Revenue Code Section 61, gross income generally means all income from whatever source derived, and unless a specific rule says it is excluded, it is taxable. In simple terms: if you got something of value and the tax law does not carve it out, the IRS probably sees it as taxable.

Explore Treasury’s 2026 Priority Guidance Plan, OBBBA implementation, regulatory changes, and what evolving IRS guidance could mean for tax planning.

Interest rates remain elevated, making every borrowing decision more important. Learn when to refinance, finance equipment, lease, or pay down debt—and how tax planning can lower your true cost of capital.

Medicaid waiver payments can create unusual tax issues because they sit at the intersection of health care, social services, and the tax code. For many caregivers, these payments are not just compensation for providing daily care; they can also affect eligibility for the Earned Income Tax Credit (EITC) and the Additional Child Tax Credit (ACTC).

For many taxpayers, cryptocurrency creates more tax issues than expected. You can owe tax even if you never convert your crypto into dollars. You can also have income even if the crypto was given to you “for free.” And if you do not keep good records, it can become difficult to calculate your gains, losses, or income correctly.

Prediction market taxation is evolving. Learn how new state laws, federal oversight, and changing tax rules could affect investors and future reporting.

Treasury is reviewing sophisticated tax-aware investment strategies. Learn what high-net-worth investors should know before implementing complex tax planning.

A Health Savings Account, or HSA, is one of the most tax-efficient accounts in the Internal Revenue Code. Its basic purpose is simple: to help people with high-deductible health plans save for current and future medical costs with favorable tax treatment. For many taxpayers, it can also serve as a long-term wealth-building tool and even a supplemental retirement account.

The IRS is updating its Voluntary Disclosure Program for cryptocurrency. Learn whatit means if you have unreported crypto transactions.

Business succession planning is the process of preparing for the futuretransfer of a business so that the company can continue operating smoothly whilealso meeting the owner’s personal, family, and financial goals.

Learn how 529 plans can help you save for education with tax advantages, flexible contribution options, and strategies for unused funds.

Thinking about buying business equipment? Learn why tax planning before you purchase can improve cash flow, financing, and long-term results.

Learn how the 2026 premium tax credit repayment changes could increase your tax bill and what steps you can take now to avoid surprises.

Workforce changes can create payroll tax nexus, contractor, trust fund tax, reimbursement, and benefits issues. Learn what to review now.

Moving or living in two states? Learn how domicile affects state taxes, residency, and audits, plus steps to protect your tax position.

Received an IRS CP53E notice? Learn why taxpayers who choose paper refund checks may wait more than two months and what you can do to avoid delays.

If you’re saving for retirement and have a modest income, the Saver’s Credit in 2026 or the Saver Match can help you fund your retirement plan.

IRS Revenue Procedure 2026-25 clarifies when family contributions to Trump accounts qualify for the annual gift tax exclusion and when a gift tax return may still be required. Learn what parents and grandparents need to know.

Reasonable compensation should evolve as your business grows. Learn why S corporation owners should review salary, distributions, and tax planning regularly.

The IRS has a maximum of ten years from the date of assessment to collect tax debts from taxpayers. This period is a crucial timeframe for anyone dealing with tax liabilities, as it essentially defines the duration the IRS can actively pursue debts. Understanding when this clock starts, potential extensions, and precautionary measures can empower taxpayers to navigate their financial obligations more effectively.

The economy is uneven, and your 2026 tax strategy should reflect your reality. Learn how growing and slowing businesses can adjust tax planning, cash flow, and expenses.

Choosing between an S corporation and C corporation involves more than tax rates. Learn the key factors that can impact growth and profits.

The IRS has announced that it will begin automatically forgiving certain penalties for taxpayers who have not had a similar penalty in the past three years, rather than requiring them or their tax preparer to request relief for them.

With gas prices soaring it has been expected the IRS would increase the mileage rate that business owners can deduct for vehicle use instead of keeping a record of actual expenses. Sure enough, the IRS recently announced a 3.5-cent increase in the optional mileage rate for business-use vehicles and a 3 cent increase for medical and moving expenses, effective for the last half of 2026.  

A mid-year tax review helps business owners improve cash flow, reduce surprises, and make smarter decisions before year-end.

Employers of all sizes can assemble a portfolio of fringe benefits that materially increase employees’ total compensation while delivering tax advantages to both the business and employees.

Many homeowners overpay by not shopping for mortgages. Learn how rates, refinancing, taxes, and cash flow can affect your finances.

A new Form 1099-DA is being initiated in 2026 for tokenized‑security dispositions.  Be ready to supply records if the broker’s basis or other data are missing.

Social Security is about more than choosing when to claim benefits. Learn how taxes, Medicare, spousal benefits, and retirement income planning work together to shape your retirement.

Learn how to identify Trump Account scams, spot warning signs, verify communications, and protect your child's savings from fraudsters.

IRMAA can raise Medicare costs for higher-income retirees. Discover planning strategies for Roth conversions, RMDs, and Social Security

Your tax outcome often depends on facts and dates. A life change that happens in June — marriage, separation, a child taking a summer job, or renting your house during a conference — can determine your filing status, eligibility for credits, and what income must be reported for the entire year.

A lawsuit involving a $21 million donor-advised fund is raising new questions about donor rights, charitable giving, and tax planning.

New Jersey's proposed $900 pet tax credit is reigniting debate over whether pet owners should receive tax relief for everyday expenses.

Florida lawmakers are pursuing major property tax changes. Here's why homeowners across the country are paying attention.