Is there a way to check online if your extension was properly processed? I made a payment two weeks ago but I'm paranoid now after reading your comment.

Yes, you can check if your extension was processed by logging into your online account at IRS.gov. Go to the Tax Records section and look for the account history or payments section. You should see your extension payment listed there with the correct tax year and payment type. If you don't see it after about 5-7 business days, I'd recommend calling the IRS to confirm. Better to deal with it now than months later when penalties might have accumulated.

This is a common misunderstanding. The extension only gives you extra time to FILE your return (until October 15th), not extra time to PAY what you owe. Any tax you owe is still due by the original April deadline. That's why you make an estimated payment when requesting the extension - to cover what you think you'll owe. If you don't pay the full amount you end up owing by the April deadline, you'll face interest charges and possibly penalties on the unpaid portion, even if you filed an extension.

Does increasing W-2 withholding actually prevent underpayment penalties the same way estimated payments do? I thought those were treated differently by the IRS.

Yes, it absolutely works! The IRS doesn't care how you pay as long as enough tax is withheld throughout the year. W-2 withholding is actually treated even better than estimated payments because withholding is considered to have been paid evenly throughout the year even if it wasn't. For example, if you realize in December that you're going to owe more, you could have extra withheld from your last few paychecks. The IRS treats that withholding as if it had been paid evenly across all quarters, which can help you avoid underpayment penalties even if your first few quarters were underpaid. Many people find this easier than keeping track of quarterly payment deadlines. Just make sure you're withholding enough total to meet your safe harbor requirement (either 90% of current year tax or 100% of prior year tax).

Try setting aside 30% of everything you make from 1099 work right when you get paid. I have a separate savings account just for taxes. That way you never "feel" like that money is yours to spend, and you're not scrambling at tax time.

That's a really good point! Also, check if you're getting the same pre-tax deductions for health insurance and FSA/HSA contributions. My refund was way different one year because my new employer's health plan was $150/month cheaper, which meant $1800 more taxable income that year.

Yes, health insurance premiums are definitely something to check too! In my case, my premium went from $220 pre-tax at my old job to $180 at the new one, which added about $480 in taxable income for the year. Another thing I discovered was that my old job had automatically enrolled me in commuter benefits that took about $100/month pre-tax, and my new job didn't have that program. Small differences like these can really add up and affect your withholding and final tax bill.

You know what, this might be part of it too! My previous job did include some overtime during our busy season, maybe 3-4 hours a week for about 2 months. My new position is strictly 40 hours. That combined with the W-4 changes everyone mentioned probably explains the difference. Thanks for pointing this out - I hadn't even considered the overtime factor.

This is super helpful! Quick question - how far back can you go with TurboTax for previous years? I haven't filed since like 2019 and I'm trying to get caught up without making the same mistake as OP.

TurboTax typically keeps the last 7 years of tax software available, so you should be able to file returns back to 2019 without issues. You'll need to download the specific software version for each tax year you need to file. Start with your oldest return (2019) and work forward chronologically. Each year's return may affect the next, especially if you're carrying forward losses or credits. Just be prepared for potential late filing penalties if you owed taxes for those years. The IRS generally has a 10-year collection period for unpaid taxes, so it's definitely good you're getting caught up now.

Yeah, prior year returns definitely get processed differently. The IRS prioritizes current year returns during tax season. Did you get any kind of notice or explanation for the delay?

Oh that's good to know! I'm in Pennsylvania - does anyone know if we have something similar here? How would I find out if my state offers rent credits?

Pennsylvania has what's called a "Property Tax/Rent Rebate Program" that might apply to you depending on your age, income, and other factors. It's primarily designed for seniors, widows/widowers over 50, and people with disabilities, but it's worth checking if you qualify. The best way to find out about rent-related tax benefits in your state is to visit your state's department of revenue website - for PA, it would be the Pennsylvania Department of Revenue site. They usually have specific sections about rebates and credits available. You can also use the IRS's Interactive Tax Assistant or contact your state tax agency directly to ask about rent-related tax benefits.

You should report what you actually paid, not what was scheduled or what your landlord claims. Check if there's a reason for the discrepancy - did you miss a payment? Did you prepay January 2024 rent in December 2023 (which would count for 2023)? Ask your landlord to explain the difference.