I work as a tax preparer and see these situations frequently. Based on what you've described, your $45,000 settlement for emotional distress and mental anguish is likely taxable income since it doesn't appear to stem from physical injuries. A few important things to consider: 1. The absence of a 1099 doesn't mean it's not taxable - you're still required to report settlement income even without formal tax documents. 2. If your settlement agreement broke down the payment into different categories (lost wages, punitive damages, emotional distress, etc.), each portion may have different tax treatment. 3. You mentioned attorney fees - this creates additional complexity. If your attorney took a contingency fee, you'll need to report the gross settlement amount as income and potentially deduct the legal fees, though recent tax law changes have made this more difficult for employment-related cases. My recommendation: consult with a tax professional who can review your actual settlement agreement. The specific language matters enormously for tax treatment, and generic advice (even from well-meaning friends who are accountants) may not apply to your particular situation. Don't wait until the last minute on this - settlement taxation can be complex and you want to get it right.

I went through something very similar last year with an employment settlement. The key thing that helped me was getting a consultation with a tax attorney who specialized in settlement taxation rather than just a regular CPA. Here's what I learned: the IRS looks at the "origin of the claim" test - basically what was the underlying reason for your lawsuit? If it was purely workplace harassment/hostile work environment without any physical injury component, then yes, it's likely taxable. However, there are some nuances that matter: - If any portion was specifically for lost wages, that's definitely taxable as ordinary income - If there were punitive damages, those are also taxable - Medical expenses you paid for therapy/treatment related to the distress can potentially be deducted For reporting without a 1099, you'd typically report it as "Other Income" on Schedule 1 of Form 1040. But definitely get professional help because the attorney fee situation can get really complicated - especially with the recent changes to itemized deduction rules. Don't let this stress you out too much though. Even if it's fully taxable, you can always set up a payment plan with the IRS if you can't pay all at once. The important thing is to report it correctly and not try to hide it.

Has anyone just manually entered their crypto transactions into TurboTax? I only have about 40 trades for the year so wondering if that's easier than dealing with all these third-party services.

I've been dealing with this exact same issue! What worked for me was using FreeTaxUSA instead of TurboTax - it has better support for importing crypto transactions directly from CSV files. I was able to upload my crypto.com transaction history with minimal formatting issues. If you're set on using TurboTax though, I found that cleaning up the crypto.com CSV file first made a huge difference. Remove any duplicate entries, make sure all dates are in MM/DD/YYYY format, and verify that buy/sell amounts match up properly. Sometimes crypto.com includes partial fills as separate transactions which can mess up the import. For the cost basis calculation differences between platforms, double-check how they're handling your staking rewards and any crypto-to-crypto trades. Those are usually where the biggest discrepancies come from.

Has anybody used the Electronic Federal Tax Payment System (EFTPS) for making estimated payments? I just signed up but it says it takes like 5 business days to get the PIN in the mail. Is there a faster way to make these payments if I need to catch up quickly?

Just want to add some reassurance here - I was in almost the exact same situation two years ago. Missed all my quarterly payments due to a miscommunication with my accountant, but had increased withholding midway through the year. The key thing that saved me was that the IRS considers your total tax payments for the year, not just whether you made the quarterly deadlines. Your increased withholding since May is actually working in your favor more than you might realize. I ended up owing a small underpayment penalty (around $200 for the whole year), but it was nowhere near the disaster I thought it would be. The penalty is calculated monthly on the underpaid amount, so even missing several quarters doesn't necessarily mean huge penalties if your withholding caught up later in the year. My advice: Don't make any rushed decisions right now. Have your CPA run the numbers first to see where you actually stand. You might find that between your increased withholding and the safe harbor rules others mentioned, you're in much better shape than you think. Sometimes the stress of thinking you messed up is worse than the actual financial impact!

For those January 1st payments, you need to apply the "constructive receipt" rule. Income is taxable when you have unrestricted access to it. If those payments weren't available to you until Jan 1, 2025, they're 2025 income regardless of what PayPal's form says.

This 1099-K situation is such a headache! I'm dealing with something similar but with Stripe instead of PayPal. I received a 1099-K from Stripe for $15,000, but only about $8,000 of that came from clients who also sent me 1099-NECs. The other $7,000 was from smaller clients who didn't send separate forms. My question is: for the clients who didn't send 1099-NECs, do I still need to worry about double reporting? It seems like the Stripe 1099-K might be the only record of those payments. Also, has anyone had luck getting payment processors to amend their 1099-K forms when there are date discrepancies? I'm wondering if it's worth the hassle or if I should just follow the constructive receipt rule that Sean mentioned. The whole payment processor reporting system really needs to be simplified. It's causing way more confusion than it's solving!

Has anyone dealt with property taxes paid to foreign governments? Can those be deducted on US taxes? I'm in a similar situation with my parents buying in Ecuador.

This is such a complex situation! Your parents definitely need to be prepared for ongoing US tax obligations. One thing I haven't seen mentioned yet is the potential impact on their state tax situation. Depending on which state they currently live in, they may need to officially establish tax residency elsewhere before moving to avoid continued state tax obligations. Also, since they're planning to split time between countries, they should be very careful about the substantial presence test. Even though they're US citizens (so it doesn't affect their filing requirement), it could impact how certain deductions and credits are calculated. I'd strongly recommend they consult with a tax professional who specializes in expat taxes BEFORE making the purchase. The timing of when they buy, when they move, and how they structure their finances could significantly impact their tax burden. Getting advice upfront could save them thousands in taxes and penalties down the road.