Most crypto investors think taxes are a once-a-year event. The IRS disagrees.
If you sold crypto at a gain in the first half of 2026, the IRS expected an estimated tax payment by June 15 — the Q2 deadline. No exchange withholds taxes for you, so unless you sent a payment yourself, nothing was sent. That's how investors rack up underpayment penalties without ever missing "Tax Day."
As an EA, this is one of the most common — and most avoidable — penalty triggers I see on crypto returns.
The safe harbor rule most investors miss:
→ Pay in at least 100% of last year's total tax (110% if your AGI was over $150K), spread across the year, and you're penalty-proof — no matter how big this year's gains are.
→ Or pay at least 90% of what you'll actually owe for 2026.
→ Next checkpoint: the Q3 estimated payment is due September 15.
If you took profits in H1 and haven't made an estimated payment yet, you still have time to limit the damage before September.
— Samuel Oduro, EA | Empower Capital | empowercapital.co