Great thread with lots of helpful insights! I went through this exact situation with my Aetna disability payments earlier this year. One thing I'd add is to check if your employer continues any benefits during your disability leave that might affect your tax situation. In my case, my company continued paying their portion of my health insurance premiums, which meant I had less taxable income than I initially calculated. This actually reduced the amount I needed to have withheld. I had to adjust my W-4S form mid-way through my leave to avoid over-withholding. Also, if you're planning to return to work part-way through the tax year, remember that your regular paycheck withholding will resume, so you don't want to double up and have too much withheld overall. I used a simple spreadsheet to track my total projected income and withholding across both my disability payments and expected regular paychecks for the remainder of the year. The key is looking at your total annual tax picture, not just the disability payment period in isolation.

This is such a helpful discussion! I'm dealing with a similar W-4S situation right now with my Aflac disability coverage. One thing I learned from my tax preparer that might be useful - if you're married filing jointly, make sure to consider your spouse's income and withholding when determining your disability withholding rate. In my case, my spouse's regular paycheck withholding was already covering a good portion of our combined tax liability, so I didn't need to withhold as much from my disability payments as I initially thought. We calculated that withholding about 15% from my disability pay (compared to the 22% from my regular paychecks) would keep us on track. Also, don't forget that if you're paying for your own disability insurance premiums with after-tax dollars, those payments are generally not taxable when you receive them. But if your employer pays the premiums (which sounds like your case with MetLife), then the benefits are taxable. This distinction can significantly impact how much you need to withhold.

Has anyone actually used crypto for contractor payments and gone through an audit? I'm worried about the exchange rate documentation. How do you prove what the USD value was at the exact moment of payment?

As someone who's been dealing with international contractor payments for the past few years, I can confirm that the IRS really doesn't care about your payment method as long as you have proper documentation. I've used everything from traditional wire transfers to crypto to digital payment platforms. The most important things to remember: 1. Always get W-8BEN forms BEFORE making any payments - this protects you from withholding requirements 2. Keep detailed records of every payment including USD value at time of transaction (especially important for crypto) 3. Connect each payment to specific invoices/work deliverables 4. If using crypto, document the exchange rate from a reliable source at the exact time of payment I switched away from wire transfers years ago due to the ridiculous fees. Currently using a mix of Wise for larger payments (great rates, professional documentation) and occasionally crypto for tech contractors who prefer it. Both have worked well during tax season and my accountant has never had issues with the documentation. The key is consistency - whatever method you choose, make sure you're documenting it the same way every time.

This is a great question that trips up a lot of people! Your W-2 should definitely show 2023 at the bottom since you're filing for the 2023 tax year. The form reports what you earned and had withheld during 2023, even though you received it in 2024. Here's a simple way to remember it: the year on your W-2 always matches the tax year you're filing for, not the year you receive the form. So when you file your 2023 return (which happens in early 2024), your W-2 should say 2023. If your W-2 shows 2024, that's definitely an error and you should contact your employer right away for a corrected form. A 2024 W-2 would be for income you haven't even finished earning yet! Before you start entering info into tax software, just double-check that the wages in Box 1 roughly match what you remember earning last year - that's another good way to confirm you have the right year's form.

This is exactly the kind of question I had when I first started doing my own taxes! Your W-2 should definitely show 2023 at the bottom since that's the tax year you're filing for. The key thing to remember is that the year on the W-2 represents the period when you actually earned the money, not when you received the form. So even though you got your W-2 in the mail in 2024, it's documenting all the wages and taxes from your 2023 work year. If it showed 2024, that would mean it's trying to report income from a year that isn't even finished yet! One thing that helped me when I was unsure was to look at my final 2023 paystub and compare the year-to-date totals with what's shown in the boxes on my W-2. If those numbers match up, you know you've got the right year's form. Good luck with your filing - asking these questions upfront will save you headaches later!

I completely understand your anxiety about this - I went through the exact same panic last year when I realized I'd used Priority Mail instead of Certified for my tax return that included a significant balance due. Here's what helped put my mind at ease: Priority Mail does include tracking that shows proof of mailing date and delivery confirmation, which the IRS will generally accept as evidence of timely filing. While it's not as legally bulletproof as Certified Mail's return receipt, it's still legitimate documentation that you met the deadline. The key thing is to preserve all your evidence right now. Print your Priority Mail receipt, take screenshots of the complete tracking history, and save the delivery confirmation. USPS tracking data expires from their website after about 120 days, so don't wait on this. In my case, my return was processed normally and I never heard anything about delivery issues. The IRS processes millions of returns sent via Priority Mail without problems. Yes, Certified Mail is the gold standard for proof of mailing, but Priority Mail tracking is still solid evidence that will protect you in the unlikely event there's ever a question about whether you filed on time. Try not to stress too much - you took reasonable steps to file by the deadline, and the tracking will back that up if needed.

I work as a tax preparer and deal with this situation frequently. Priority Mail is actually accepted by the IRS as proof of timely filing - the tracking number serves as evidence that you mailed your return by the deadline. While Certified Mail provides stronger legal protection with its return receipt, Priority Mail tracking showing delivery to the IRS processing center is generally sufficient. The most important thing right now is to save all your documentation. Print your Priority Mail receipt and take screenshots of the complete tracking history, including the delivery confirmation. This tracking data will only be available on the USPS website for about 120 days, so don't delay in preserving this evidence. In my experience, the vast majority of Priority Mail tax returns are processed without any issues. The IRS receives millions of returns via Priority Mail each year. Your tracking confirmation showing timely delivery should protect you if there's ever a question about meeting the filing deadline. While I always recommend Certified Mail for high-stakes situations, you shouldn't lose sleep over using Priority Mail - just make sure to keep that proof of delivery safe.

Just want to make sure the OP and others understand capital gains taxes for 2025 filing. If you hold your investments for more than a year before selling (long-term capital gains), you get a much better tax rate (0%, 15%, or 20% depending on your income) than short-term gains (taxed as ordinary income). Making this distinction could literally save you thousands on your tax bill! I learned this the hard way when I day-traded some stocks and got hit with ordinary income rates on everything.

Great advice from everyone here! Just want to add one more consideration for @Ava Kim - since you're working at Target and trading stocks, you might want to look into tax-loss harvesting if you have any losing positions. You can sell losing stocks to offset your capital gains, which reduces your overall tax liability. For example, if you made $30k in gains but also have $10k in unrealized losses, you could sell those losing positions to bring your taxable gains down to $20k. You can even carry forward losses beyond your gains (up to $3k per year against ordinary income). This strategy works best when combined with the estimated payment approaches others mentioned. Just make sure to avoid the wash sale rule - don't buy back the same or "substantially identical" securities within 30 days of selling for a loss, or the IRS will disallow the loss deduction.