deepdive.

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 what it means if you have unreported crypto transactions.

Business succession planning is the process of preparing for the future transfer of a business so that the company can continue operating smoothly while also 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 m...

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.