Do offshore betting sites send any tax forms? I've been using [redacted site] for years and never received anything, but also never reported any of it. Now I'm worried...

Offshore betting sites typically don't issue tax forms or report to the IRS since they're operating outside US jurisdiction. However, that doesn't exempt you from the obligation to report your gambling winnings - all gambling income is technically taxable regardless of where it comes from. The lack of reporting from offshore sites creates a documentation gap that puts the burden entirely on you to track and report accurately. If you've had significant winnings, you might want to get your past reporting in order. The IRS has been increasingly focused on unreported gambling income, especially with cryptocurrency transactions sometimes being used for offshore gambling.

The tax code distinguishes between investments and gambling based on the nature of the activity. Business investments are considered productive economic activities, while gambling is viewed as recreational. That said, if you can document that your gambling activities constitute a trade or business (extremely difficult to prove - requires regular, full-time activity with a profit motive), you might be able to deduct losses on Schedule C instead of Schedule A. But for the vast majority of people who gamble occasionally, the IRS will only allow losses to offset wins when itemizing.

I've always checked "single" since I'm not married and don't have dependents. Didn't realize head of household might apply! I do have some student loans but they're pretty new. How would I know if I qualify for HOH status?

To qualify for Head of Household, you generally need to be unmarried and pay more than half the cost of keeping up a home for yourself and a qualifying person (like a dependent child). If you live alone or with roommates but don't support a qualifying dependent, you'd still file as Single. For student loan interest, you can deduct up to $2,500 in interest payments per year, depending on your income. You should receive a Form 1098-E from your loan servicer showing how much interest you paid. Even new loans can generate interest while you're in school, so definitely look into this!

This! My employer had me as "married" instead of "single" on my W-4 for some reason, which meant they were withholding at a lower rate. Took me three years to figure this out! Check your paystub and see what filing status they're using for your withholding.

Does every state tax early withdrawals the same way though? I thought some states don't tax retirement distributions at all, while others follow the federal rules including the penalty?

You're absolutely right that states vary in how they handle retirement distributions. Some states like Wyoming, Florida, Texas, and others have no state income tax so there's nothing to worry about there. Other states follow the federal treatment and will tax the full amount as income, plus some even add their own early withdrawal penalties on top of the federal 10%. Then there are states with special exemptions or lower tax rates for retirement income, but these often don't apply to early withdrawals. For example, Illinois doesn't tax qualifying retirement income, but early withdrawals might not qualify for that exemption.

Yes, that's exactly what the calculator is designed to do! When you enter the IRA distribution in the "other income" section and include any withholding already taken from that distribution, the calculator will recommend adjusting your W-4 to withhold more from your remaining paychecks this year to cover the additional tax liability.

Thanks for this suggestion! Would the IRS consider my taxes "paid on time" if I cancel the direct debit and then use Direct Pay on April 15th instead? I don't want to trigger any late payment penalties.

Yes, as long as you complete the Direct Pay transaction by midnight on April 15th, the IRS considers your payment made on time. The confirmation page you receive serves as proof of timely payment. Just make sure to select "2024" for the tax year and "1040 series" for the reason for payment when you use Direct Pay. Also, keep a copy of your payment confirmation number in case there are any questions later.

That's odd, in my experience the IRS is actually very precise with their direct debit dates. They took mine exactly on the date I specified. Maybe it was your bank that caused the delay?

Is it ever worth paying for both at the same time? Like could they work together on a complicated situation?

Absolutely! In complex situations, having both professionals work together can be extremely beneficial. For example, if you're creating a complex estate plan or setting up a business with significant tax implications, your CPA can provide the financial projections and tax calculations while your tax attorney ensures the legal structures are optimal. Many high-net-worth individuals and businesses have both a CPA and tax attorney on their professional team. They typically use the CPA for ongoing tax work and consult the attorney for specific legal tax matters. The cost is justified when the potential tax savings or risk mitigation significantly outweighs the professional fees.

This is so important! I learned this the hard way when my CPA had to provide information to the IRS during my audit. Nothing illegal, but certainly embarrassing and led to more scrutiny.