One tip about filing these old returns - don't e-file! The IRS only accepts electronic filing for the current tax year and 2 years prior. For anything older than that, you have to mail paper returns. Also, be sure to mail each tax year in a separate envelope. If you send multiple years together, it increases the chances of processing errors.

Just wanted to add something that might help with your peace of mind - even though you can't recover that 2017 overpayment, filing both returns will at least give you a complete picture of your tax situation from those years. I was in a similar boat with unfiled returns and kept putting it off because I was overwhelmed by all the unknowns. Once I finally bit the bullet and filed everything, it was honestly such a relief to have it done and know exactly where I stood with the IRS. One thing that helped me was creating a simple spreadsheet tracking what I owed for each year including estimated penalties, so I could budget for the payments. The uncertainty was actually worse than the reality of what I ended up owing. Good luck getting everything sorted out - you're already taking the right steps by researching this and planning to file!

Don't feel bad, I've been through this every year for 5 years now and still get anxious! Quick tip - set a calendar reminder for early January next year to request tax info from the daycare. Most are prepared for this question in Jan/Feb but get annoyed by April when they've answered it 100 times already. Also, if you're using TurboTax, it actually has a feature where you can look up provider EINs if you used the same daycare last year. Saved me when one of our providers changed ownership and I needed the new EIN.

Great question! I went through this exact same stress last year with my twin boys at two different daycares. Here's what worked for me: Most daycares are totally used to this request, especially during tax season. Just call and say "Hi, I'm preparing my taxes and need your EIN and the total amount I paid for childcare in 2024 for tax reporting purposes." That's it! A few things that helped me: - Call during business hours but not pickup/dropoff times when they're swamped - Have your child's name and your account info ready - Ask if they have a standard form they provide to parents for tax purposes If you paid by credit card or check, your bank statements can help verify the amounts. I actually created a simple spreadsheet tracking all payments which made everything so much easier. Don't overthink it - you're just asking for basic business information that every legitimate childcare provider should readily provide. You've got this!

Another approach - have you tried explaining to your contractor that they REALLY need to give you their info? If they're a legitimate business, they should understand this is required. I've had success with telling contractors that I'm legally required to report payments over $600, and without their SSN/EIN, they might face issues with the IRS themselves. Sometimes they just don't understand the importance. You might also want to have them complete a W-9 form which officially requests their tax ID information. Send it with a gentle but firm explanation that you cannot make future payments without this completed form.

Great question! I went through this exact situation last year with a freelance graphic designer. You absolutely can e-file your personal return through TurboTax and mail the 1099-NEC/1096 forms separately - they're completely independent processes. For your personal return, just claim the $1,800 deduction on your Schedule C (or Schedule C-EZ) as usual. The IRS doesn't require you to have the contractor's TIN to claim legitimate business expenses. For the 1099-NEC, fill it out with "Applied For" in the TIN field and mail it with Form 1096 to your state's designated IRS processing center (you can find the address in the 1099 instructions). Make sure to keep copies of all your attempts to get their SSN/EIN - emails, texts, certified mail receipts, etc. One tip: Send the contractor a formal W-9 request via certified mail with return receipt. This creates an official paper trail and sometimes the formality finally gets them to respond. You can download the W-9 from IRS.gov. Don't let this contractor's lack of cooperation delay your filing or cost you a legitimate deduction!

I went through this exact same situation last year and it was so stressful! Like others have mentioned, the IRS doesn't automatically withdraw payment even when you provide banking info - that's only for refunds. I ended up using IRS Direct Pay and it was super straightforward. The key things to remember: 1. You have until April 15th to make your payment without penalties 2. Direct Pay is completely free (no processing fees like credit cards) 3. You'll need your AGI from your tax return to verify your identity 4. You get an immediate confirmation number for your records Since you filed about 10 days ago, you still have plenty of time. Don't stress too much - this is a really common confusion! I'd recommend making the payment within the next week or so just to get it off your mind. The relief of having it done is worth not waiting until the last minute. The IRS website can be a bit overwhelming, but once you navigate to the Direct Pay section, the actual payment process is pretty simple. Just make sure you double-check all your account info before submitting!

Just want to echo what everyone else is saying - you definitely need to make a separate payment! I made this exact mistake a few years ago and ended up with penalty fees because I thought the IRS would automatically withdraw the money. The good news is you still have time since you filed recently. I'd recommend using IRS Direct Pay like others mentioned - it's free and gives you instant confirmation. Just go to irs.gov/payments and look for the "Direct Pay" option. One thing I learned the hard way: don't wait until the last few days before April 15th. Even though Direct Pay processes quickly, you don't want to deal with any potential website issues when thousands of people are trying to pay at the last minute. I now make my payment within a week of filing just to avoid the stress. The whole "filing vs paying" distinction confused me too when I first owed taxes. Think of it this way: filing your return is like sending the IRS a bill that says "here's what I owe you," but actually paying is a separate transaction where you settle that bill. Hope this helps ease your worries!

Another option worth considering is filing Form 8832 first to elect to be taxed as a C Corporation, then immediately filing Form 2553 for S Corp status. Sometimes this two-step approach can work outside the normal S Corp election deadline. Talk to your accountant about this strategy - it's worked for some clients at our firm.

Don't forget that even if you successfully convert to an S Corp, you need to run payroll and pay yourself a "reasonable salary" before taking any distributions. Many people miss this and end up with IRS problems. My brother tried taking mostly distributions with a tiny salary and got hit with penalties for avoiding payroll taxes.