What dates count for tax return filing? Would Jan 1, 2024-Dec 31 2024 pay be calculated for 2024 W-2?

For almost all regular employees, your tax year is based on when you actually receive payment, not when you earned it. This is called the "cash basis" of accounting. For your W-2, it includes all wages that were paid to you between January 1, 2024 and December 31, 2024. So that bonus you received in early January 2024 will be on your 2024 W-2, even though it was for work done in 2023. The timing of when you did the work doesn't matter - it's when you got paid. For your freelance work, if you don't receive payment until January 2025, that income would be reported on your 2025 tax return (which you'll file in 2026), not your 2024 return. Again, it's when you receive the money that counts.

I went through the exact same confusion last year trying to figure this out! I found this amazing tool at https://taxr.ai that actually analyzes all your tax documents and tells you exactly which tax year they belong to. It was super helpful because I had some 1099 work plus regular W-2 income and couldn't figure out what went where. The tool breaks everything down by date and shows you what falls into each tax year. You just upload your documents and it extracts all the relevant info automatically. It saved me tons of time trying to sort through everything myself, especially with some payments that crossed over between years.

Just wanted to follow up about that taxr.ai site I was skeptical about. I ended up trying it because I had a complicated situation with some investment income, freelance work, and a job change all in the same year. It was actually really helpful! The document analysis is crazy accurate - it caught that my side gig had paid me in January 2025 for December 2024 work and correctly put that in the 2025 tax year section. The date sorting feature is exactly what I needed. Now I know for sure which tax years all my income belongs to. Sorry for being suspicious before, but with financial stuff you can't be too careful. Glad I gave it a shot though.

If anyone's as frustrated as I was trying to get answers directly from the IRS about tax year questions, check out https://claimyr.com - it's a service that gets you through to an actual IRS agent instead of waiting on hold for hours. You can watch how it works at https://youtu.be/_kiP6q8DX5c I had this exact question about some stock sales where the trade date was in 2024 but the settlement date was in 2025, and I couldn't figure out which tax year to report it in. After trying for days to reach the IRS myself, I used Claimyr and got connected to an agent in under 20 minutes who confirmed it's the trade date that matters for stock sales, not the settlement date.

I have to eat my words about Claimyr. After my skeptical comment, I decided to try it myself since I'd been trying to reach the IRS for weeks about some confusing 1099 forms with incorrect dates. I couldn't believe it actually worked! Got connected to an IRS rep in about 25 minutes when I'd previously spent 3+ hours on hold multiple times and never reached anyone. The agent explained that for 1099 forms, it's all about when I received the payment, not when I performed the service. So even though I did the work in December 2024, since I was paid in January 2025, it counts for tax year 2025. Same rule for W-2 income. Totally worth it just to get a definitive answer directly from the IRS instead of guessing.

Another important date thing to remember is that if you're self-employed and make estimated tax payments, the deadlines are weird - they're not all 3 months apart like you'd expect. For 2024 taxes, payments are due April 15, June 17, September 16, 2024, and January 15, 2025. Also don't forget that for some tax benefits like IRA contributions, HSA contributions, etc. you actually have until the tax filing deadline (usually April 15, 2025 for 2024 taxes) to make contributions that count for the previous year.

Ok but what about stuff thats a little more complicated? I had a situation where I sold an item on ebay on Dec 30 2024 but the money didnt hit my account until Jan 3 2025 and paypal sent me a 1099-K for 2025. But the actual sale happened in 2024. Which year is this supposed to be reported for?

Just to add another perspective on timing that might help others - retirement account withdrawals follow the same "when you receive it" rule. I had an early 401k withdrawal in late December 2024, but my former employer didn't process it until January 2025. Even though I requested it in 2024, it shows up on my 2025 1099-R because that's when I actually received the funds. This timing can actually be strategic if you're trying to manage your tax bracket - you might want to delay a withdrawal to the following year if you've already had a high-income year. Same goes for things like cashing out unused vacation days or exercising stock options. The key is always when the money hits your account or you receive the check, not when you initiated the transaction.