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Dude don't overthink this! Nobody is matching your VPN activity to your tax returns. I've been trading on "not approved for US" exchanges for years. Just report the gains accurately and you're fine. I use CoinTracker to organize all my trades across different exchanges and it spits out the right forms. The government cares about getting their tax money, not which website you got your coins from. Just my 2 cents worth of crypto lol
But what about when you have to transfer money back to your bank? Doesn't that create a paper trail linking you to the exchange?
Yes, there's always a paper trail when you move money back to your bank, but that doesn't change the main point. The banking system knows you received funds from somewhere crypto-related, but that alone doesn't tell them which specific exchange you used or whether that exchange was "approved." Most important thing is just to report all your income accurately. The IRS wants their cut of your gains - that's their primary concern. They're not coordinating with other agencies to check if you used a VPN to access certain websites. They have bigger fish to fry than retail traders who are actually paying their taxes properly.
Has anyone considered that some exchanges now report to the IRS through 1099-K forms? If you made over $20k in total transactions (not just gains), some exchanges might send your info directly to the IRS even if they're international.
This is partly true but misleading. Only US-regulated exchanges are required to issue 1099-K forms. International exchanges that don't have US operations typically don't issue these forms because they're not subject to US reporting requirements. That's part of why they can offer coins not available on US platforms.
One thing nobody's mentioned - keep track of ALL YOUR EXPENSES that might be tax-related! I learned this the hard way. If you're a regular W-2 employee (like at a store or restaurant) it's pretty simple, but if you do ANY side work or freelancing, keep receipts for EVERYTHING related to that work. Apps, supplies, mileage, part of your phone bill, internet, etc. Also, if you're in school, keep records of tuition and books! There are education credits that can save you $$.
When I was 20 I thought getting a big tax refund was awesome... until my econ professor explained I was just giving the govt an interest-free loan all year lol. If u get a huge refund, consider adjusting ur W-4 withholding so u get more $$ in each paycheck instead of waiting for a refund. Its YOUR money!
This is actually really bad advice. Most ppl aren't disciplined enough to save that extra money each paycheck. Getting a refund is forced savings for a lot of people. If your getting the money in small amounts each check, lots of ppl just spend it without noticing. I purposely have extra withheld so I get a big refund every year. Use it to pay down debt or take a vacation. Different strategy works for different folks.
Another option you have is to "recharacterize" that $500 from each Roth IRA to Traditional IRA. This effectively treats it as if you originally contributed to a Traditional IRA instead of a Roth. If you're over the Roth income limits, you're probably also over the deductible Traditional IRA limits if you have workplace retirement plans, so the $500 would be a non-deductible Traditional IRA contribution. This could be useful if you're planning to do a backdoor Roth conversion at some point.
Thanks for this suggestion. If I recharacterize to Traditional, would I need to file any special forms with my taxes this year? And can I just open a Traditional IRA now even though the contribution was technically made in 2023?
Yes, you would need to file Form 8606 with your tax return to report the non-deductible Traditional IRA contribution. This is important because it establishes your "basis" in the Traditional IRA, which will matter for tax purposes if you ever convert that money to a Roth in the future. You can open a Traditional IRA now even though the contribution was for 2023. The recharacterization process will treat it as if you made the contribution to the Traditional IRA in the first place. Just make sure you complete the recharacterization before your tax filing deadline (including extensions).
Wait, I'm confused about something. If you're at the income limit for Roth contributions, wouldn't the phase-out mean you can contribute SOME amount rather than nothing? Like if the phase-out range starts at $218k and ends at $228k for married filing jointly, and you're somewhere in that range, you should be able to calculate the exact amount you can contribute. FreeTaxUSA should do this calculation for you.
Something nobody mentioned yet - if you take a 401k loan and then have any financial hardship that makes it hard to repay, you're in a terrible position. I borrowed $25k three years ago, then had some medical issues and couldn't keep up with payments. When it defaulted, it was treated as a distribution, so I owed income tax PLUS the 10% penalty. Ended up with a surprise $8,500 tax bill the following April that I couldn't afford, which created even more financial problems. Also consider that many people who take 401k loans are already in a tight financial spot - that's why they need the money. But that also means they're at higher risk of not being able to repay if anything else goes wrong.
I'm so sorry that happened to you. This is exactly the kind of situation I'm worried about. Were there any options to renegotiate the loan terms when you realized you were having trouble making payments?
Unfortunately, 401k loans have very rigid repayment terms set by the IRS and your plan administrator. Unlike other loans, there's typically no hardship program or way to restructure the debt. The only flexibility my plan offered was a one-time 3-month suspension of payments, but that just meant larger payments later to catch up. Once you miss payments beyond what your plan allows (in my case, it was 90 days), the outstanding balance is automatically considered a distribution. At that point, there's nothing you can do - the money is considered withdrawn, triggering the taxes and penalties. The worst part is this usually happens when you're already facing financial difficulties, making the tax consequences even harder to manage.
I took a 401k loan last year and honestly regret it. Beyond all the technical downsides others mentioned, there's also the psychological aspect. Once I realized how easy it was to access that money, it became tempting to see my retirement account as an emergency fund rather than untouchable retirement savings. Also, the repayment is usually automatic from your paycheck, which sounds convenient but it reduced my take-home pay. This made my monthly budget tighter and actually led to more credit card debt because I had less cash flow. The "interest to myself" sounded great in theory but didn't feel like any benefit in practice.
I had the opposite experience! Took a $15k loan to consolidate high-interest debt, and seeing that automatic payment come out each month was actually motivating. Paid it back in 3 years and it helped me build better financial habits. I think it depends on what you're using it for and your personal discipline.
Liam McGuire
One thing nobody has mentioned yet - if your grandmother had any outstanding debts when she passed, the estate should pay those before distributing assets to beneficiaries. If the executor didn't handle this properly and creditors come after the estate later, beneficiaries can sometimes be asked to return distributed assets. Not trying to scare you, but it's something to check with the executor about. Did they publish notices to potential creditors and wait the required period before distributing assets?
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Yuki Sato
ā¢Oh man, that's concerning. I have no idea if the executor did that. It's my uncle (dad's brother) handling everything. I'll definitely ask him about this. How long do they usually need to wait before distributing?
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Liam McGuire
ā¢The waiting period varies by state, but it's typically between 3-6 months after publishing notices to creditors. In Texas, I believe it's 4 months. A properly handled estate administration should include this step, but family-member executors sometimes skip parts of the process if they're not working with an attorney. Just check that your uncle published the required notices and waited the appropriate time. If he worked with an estate attorney, they would have ensured this was done correctly.
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Amara Eze
I inherited money last year and completely forgot to mention it to my tax preparer. Should I be worried? Do I need to file an amended return?
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Carmen Ruiz
ā¢You're most likely fine. If it was a straightforward inheritance (not from an IRA or retirement account), you typically don't need to report it on your tax return at all. Inheritances generally aren't considered taxable income to the beneficiary. The only exception would be if you inherited something that was generating income after the person died (like interest, dividends, rental income, etc.) - in that case, you would need to report that income, but not the inheritance itself.
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