But does TurboTax help with tracking the losses properly? I'm always confused about what documentation I need to keep, especially for smaller amounts where the casino doesn't issue any forms.

TurboTax has a good section that explains what documentation you need to keep, but it doesn't actually help you create or maintain the gambling log itself. You still need to track all your sessions with dates, locations, game types, and amounts won/lost. For the smaller amounts without forms, the guidance is clear that you should still report all winnings as income and track all losses that you want to deduct. They recommend keeping all betting tickets, receipts, bank records showing casino withdrawals, and statements from player's club cards. The software is helpful for the actual tax filing part, but the record-keeping is still on you throughout the year.

Oh, I didn't think to check that. I did hit one slot jackpot that was over $1,200 and they did paperwork before paying me. I need to find that form to see if they withheld anything. Does that withholding count like a regular paycheck withholding toward my total tax bill?

Yes! Any taxes withheld from your gambling winnings shown on a W-2G form count exactly like regular paycheck withholding toward your total tax bill. It's treated as if you've already paid that portion of your taxes for the year. This is especially important with larger jackpots because it helps you avoid underpayment penalties that might otherwise apply if you suddenly have a big chunk of income with no withholding. Make sure you find all your W-2G forms and report them correctly. The IRS automatically gets copies of these forms from the casino, so they'll know if you miss reporting one. The form will have your winnings amount in Box 1 and any federal tax withheld in Box 4.

Is this the "Get Transcript" feature? I looked at that but got confused about which option to select.

Yes, it's through the Get Transcript service. You'll need to select "Wage and Income Transcript" when prompted for the type of transcript. This will show information from forms submitted to the IRS including W-2s and 1099s. Creating an account can be a bit of a process since they've increased security measures. You'll need your ID, social security number, and some financial account numbers for verification. Once you're in, you can access transcripts for the current tax year and previous years.

This! Employers sometimes do this when they haven't been paying the proper employment taxes. Definitely report them to both the IRS and state labor board. Make them face consequences!

Do we need to request transcripts before filing amendments? I assumed I just need my original return copy. Also, how far back can you amend returns? I might have similar issues with my 2021 taxes.

You don't absolutely need transcripts before filing amendments, but they're extremely helpful to ensure you have the exact information the IRS has on file. Having your own copy of your return is good, but the transcript shows how the IRS actually processed it, which sometimes differs from what you submitted. For amended returns, you generally have 3 years from the original filing date or 2 years from when you paid the tax, whichever is later. So for 2021 taxes (typically filed in 2022), you should still be within the amendment window for the 2025 filing season. I'd recommend grabbing the transcript though - it makes the amendment process much smoother when you can see the IRS's internal codes and processing marks.

That's a good point about tax preparers! My accountant uses checkmarks and little symbols all over my returns before submitting. I always thought it looked so messy but I guess that's their system.

Thanks for bringing this up! I double-checked, and you're right - the documents are actually from my tax preparer's office, not directly from the IRS. They sent me copies of what they submitted. That makes so much more sense why there are these little marks all over them. I feel kinda silly now for worrying, but at least I understand what I'm looking at. Guess my preparer was just marking things they verified before submitting. Learning something new about taxes every day!

Thanks for sharing your experience! Did you end up having to file an amended return, or were you able to get it resolved by just responding to the IRS notice?

I didn't need to file an amended return. I just responded to the IRS notice with a detailed explanation and a copy of my 1099-R. I highlighted Box 1 and Box 5 showing the identical amounts and explained these were after-tax contributions being returned. The IRS accepted my explanation and canceled the proposed adjustment about 6 weeks later. They sent a letter confirming no additional tax was due. Just make sure to respond within the deadline given on the notice, and keep copies of everything you send them.

I called about a similar issue last year. If you can actually reach someone (big if), they can be helpful. I got through after 3 attempts and about 90 minutes on hold. The agent was able to see that my 1099-R boxes matched and noted my account that no additional tax was due. Still got a confirmation letter about a month later.

Good point about state taxes! I live in a state with no income tax so I totally forgot about this aspect.