Lost receipts do not necessarily mean every business deduction is lost. Under the Cohan Rule, courts may sometimes estimate legitimate expenses when there is credible evidence that the expenses were actually incurred. But the rule has important limits, and certain expenses are subject to stricter IRS substantiation requirements.

Eligible children may receive a one-time $1,000 federal contribution to a Trump Account. Learn who qualifies, how parents can submit IRS Form 4547, and what families should know about opening and activating a Trump Account.

Owning a small business does not automatically prevent you from filing bankruptcy. Learn how Chapter 7, Chapter 13 and Chapter 11 may apply to self-employed individuals, sole proprietors, LLC owners and other small business owners.

An HSA can do much more than pay current medical bills. Learn about its tax advantages, 2026 contribution limits, investment potential and how saving medical receipts may allow you to reimburse yourself tax-free years later.

Beginning in 2026, federal law generally limits the gambling-loss deduction to 90% of wagering losses. Learn why even a gambler who breaks even could face taxable income and how Massachusetts gambling-loss rules can create additional tax complications.

Got a letter from the IRS or Massachusetts DOR? Learn why tax notices are sent, what to look for, and the steps to take before responding.

HSA withdrawals may be tax-free when used for qualified medical expenses, but they still must be reported. Learn why Form 1099-SA and Form 8889 matter at tax time.

Thinking about tapping your 401(k) for a home or expenses? In Massachusetts, early withdrawals often trigger federal tax, a 10% penalty, and state tax—turning “easy cash” into a 37% hit or worse. Read this before you make an expensive mistake.