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Just want to add something nobody's mentioned - if you're audited for those gambling losses, the IRS will want to see that you had the financial means to sustain those losses. So if you're claiming $13,000 in gambling losses but your income for the year was only $40,000, they might question how you afforded to lose that much gambling. Make sure you can demonstrate that you had access to the funds that you supposedly lost. Bank withdrawals near casino locations are helpful for this. Otherwise, they might disallow some of your loss deductions if the amounts seem unreasonable compared to your income and other expenses.

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Zoe Walker

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That's a really good point I hadn't considered. I make about $65,000 a year, and I've probably lost around $9,000 gambling this year (sadly). Would that raise red flags? Most of those losses were small amounts over many casino visits throughout the year.

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That level of losses relative to your income likely wouldn't raise immediate red flags, especially since it's spread out over multiple visits rather than a few large losses. The IRS understands that people don't typically lose their entire gambling budget in one session. Just make sure you've got some supporting evidence beyond just the losing tickets - bank withdrawals at casino ATMs, credit card statements showing charges at gambling establishments, etc. The more documentation you have connecting your financial activity to your claimed gambling losses, the stronger your position would be if questioned. And remember, you're only claiming these losses to offset the winnings you already reported - you're not trying to generate a tax loss beyond that.

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Mateo Silva

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I work at a casino and here's a tip many people don't know: if you're a regular gambler, ALWAYS use a player's card when you gamble. Not only do you get comps, but most casinos can provide you with an annual win/loss statement if you request it. This is GOLD for tax purposes! Way better than trying to recreate a gambling log after the fact.

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Does the player's card tracking actually work for slots too? I mostly play slots and video poker and wasn't sure if those machines track losses accurately.

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22 Something people often overlook with Roth contributions is that you need to have TAXABLE compensation to contribute. So if all your income for the year was from workers comp, unemployment, or investment returns, you can't contribute anything to a Roth IRA that year. The compensation has to be taxable earned income like W-2 wages, self-employment income, or alimony (from pre-2019 divorces).

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11 Wait so does disability payments count as earned income for Roth IRA purposes? I've been on short-term disability for a few months but still contributing to my Roth.

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22 No, most disability payments don't count as earned income for Roth IRA purposes. Short-term disability payments from your employer or an insurance company are generally considered taxable income, but they're not considered earned income for IRA contribution eligibility. The only exception would be if you're receiving disability payments from Social Security and you've previously opted to have those benefits taxed as wages. But that's pretty uncommon and requires specific prior arrangements with the SSA.

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7 If you already filed your taxes, remember you'll need to file an amended return to correct this. You'll need to file Form 5329 to report the excess contribution and either pay the 6% penalty or show that you withdrew the excess (plus earnings) by the deadline.

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1 Thank you! I haven't filed yet for 2024, so I'm trying to fix this before I submit anything. Do I still need to file Form 5329 if I withdraw the excess before filing?

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You don't need to match expenses to specific 1099s unless they are for completely different types of businesses. The IRS wants you to file one Schedule C per business type, not one per client. For example, if you got three 1099-NECs for graphic design work from different clients, that's ONE Schedule C with all three 1099s added together as income, and ALL related expenses listed. But if you got a 1099-NEC for graphic design and another for tutoring, those would be TWO different Schedule Cs because they're different business types. In FreeTax, after you enter all income, look for "Business Expenses" or "Schedule C Expenses" section - that's where you'll add ALL expenses for that business type.

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Diego Flores

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This was confusing me too. So if I drive for both Uber and Lyft, that's one Schedule C total? But if I drive for Uber and also do web design, that's two different ones?

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Exactly right! Uber and Lyft would be considered the same business type (driving/transportation services), so you'd file one Schedule C combining that income and all related car expenses, phone expenses, etc. But if you drive for Uber and also do web design, those are completely different businesses, so you'd file two separate Schedule Cs - one for the driving income/expenses and another for the web design income/expenses.

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I had a similar issue with FreeTax. The solution for me was to complete the ENTIRE income section first (all W-2s, 1099s, etc.) before the expense page became available. Don't look for expense options while entering each 1099-NEC. Instead, after entering all income sources, look for a section called "Business Expenses" or "Self-Employment Deductions" in the main menu. Also, make sure you correctly answered the question about whether these 1099s are for the same business or different businesses. If you indicated different businesses, FreeTax should give you separate expense sections for each.

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This worked for me! I needed to finish ALL the income entry first, then go back to the business section. Thanks for spelling it out so clearly.

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Have you tried just manually filling out Form 8965 and attaching it to your return? I had a similar issue with TaxAct last year and ended up just downloading the form from the IRS website, filling it out by hand, and attaching it to my printed return. For 2018, you can use exemption code G for general hardship on Form 8965, Part III. You don't need an ECN - just enter the code and the months it applies to. If you're e-filing, you might need to try different tax software, but if you're mailing your return, this workaround definitely works.

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Aaron Boston

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Would I still use TurboTax to do the rest of my return and just attach this form separately? I'm a little worried about how that would work with e-filing. Has anyone successfully done that?

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You'd still complete the rest of your return in TurboTax, but when it comes to filing, you'd need to print and mail the return instead of e-filing. Just print everything from TurboTax, then attach your manually completed Form 8965. The downside is you'd have to paper file, which means a slower refund if you're getting one. But it's better than paying a penalty you don't owe! Another option might be to check out FreeTaxUSA or another software that might have updated their systems correctly for the 2018 hardship exemption changes.

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Kaitlyn Otto

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Just to confirm what others have said - I was in the exact same situation for my 2018 taxes (unemployed most of the year). I ended up switching from TurboTax to FreeTaxUSA which handled the hardship exemption correctly without asking for an ECN. It let me enter exemption code G directly on the equivalent of Form 8965 and calculated everything correctly. Might be worth trying if you don't want to paper file or deal with calling the IRS. Their deluxe version is also way cheaper than TurboTax if you still need to file.

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Axel Far

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Was it complicated to switch software mid-way through doing your taxes? Did you have to re-enter everything?

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Ethan Brown

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You should immediately consult with a trust litigation attorney. The accountant's obligations are important, but your primary concern should be protecting the remaining trust assets ASAP. In my experience, once a trustee starts misappropriating funds, they rarely stop voluntarily. Your attorney can seek a temporary restraining order to freeze the trust accounts while the investigation proceeds. Also, document EVERYTHING from this point forward - every conversation, email, and phone call related to the trust. Keep copies of all statements and documents you receive. This documentation will be crucial for any legal proceedings.

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What kind of attorney should I look for specifically? Is there a certain specialty that deals with trustee misconduct? And roughly what should I expect this to cost? I'm worried about spending a ton on legal fees when the trust assets have already been diminished.

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Ethan Brown

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You want an attorney who specializes in trust and estate litigation specifically - not just any estate planning attorney. Many estate planners focus primarily on creating trusts and wills but have limited experience with litigation when things go wrong. Look for terms like "trust litigation," "fiduciary litigation," or "trust disputes" on their website or firm description. Ideally, find someone who has experience specifically with trustee removal cases and financial misconduct. Regarding costs, most trust litigation attorneys work on an hourly basis, typically $300-$500 per hour depending on your location and the attorney's experience. Many states allow for attorney fees to be paid from the trust itself when the litigation benefits the trust (like removing a dishonest trustee), but this usually happens after the case concludes. You might need to pay upfront and seek reimbursement later.

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Has anyone considered criminal charges? When my cousin stole from our family trust, we initially just tried to remove her as trustee. But our attorney explained that trustee theft over certain amounts is actually felony embezzlement in most states. Filing a police report created a lot more pressure and ultimately led to a much better settlement because she wanted to avoid prosecution. Just something to consider alongside the civil remedies.

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Carmen Ruiz

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This is an important point. My family went through something similar, and we found that once we filed a police report, the trustee suddenly became much more cooperative with returning funds. The district attorney in our county had a financial crimes unit that took it quite seriously.

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