I just want to add that the standard deduction vs. itemizing decision should look at your TOTAL tax picture, not just Form 8960. Sometimes it's actually better to itemize even if it's slightly less than the standard deduction because of the impact on other forms like 8960. Have you run the numbers both ways to see which gives you the lowest overall tax?

Great point about running the numbers both ways! I actually did a quick calculation after reading your comment and you're absolutely right - even though itemizing would give me about $2,100 less in deductions compared to the standard deduction, the ability to use my investment interest expense on Form 8960 would save me roughly $450 in NIIT. So net effect: I'd pay about $500 more in regular income tax by itemizing, but save $450 in NIIT, making the total difference only about $50. Given how close it is, I might actually itemize just to have those legitimate expenses recognized somewhere on my return. This is exactly why tax planning can be so tricky - you really do need to look at the whole picture, not just individual forms. Thanks for the perspective!

Don't forget that any business expenses you had during those contractor months might be deductible on your Schedule C! This includes things like mileage if you drove for work, a portion of your phone bill if you used it for work, home office deduction if you worked from home, etc.

One thing to keep in mind is that when you file your 2025 taxes, you'll likely need to make quarterly estimated tax payments for 2025 if you expect to owe $1,000 or more in taxes. Since you now have both W-2 income and potential future contractor income, it's worth calculating this early to avoid underpayment penalties. Also, make sure your employer provides you with both a 1099-NEC for those contractor months AND a W-2 for your employee months. Some employers try to just issue a W-2 for the whole year, but that's incorrect - the contractor income needs to be reported separately on the 1099-NEC. If your employer pushes back on issuing both forms, you can point them to IRS guidelines that clearly state the income must be reported according to how you were classified when you earned it, not your status at year-end.

Has anyone else just switched to e-filing their extensions? After having a paper extension get lost a few years ago (and paying penalties because of it), I've gone completely digital. Most tax software lets you e-file the extension for free, even if you end up filing your actual return on paper later.

Great question! I had the same confusion when I first filed an extension by mail. You're absolutely correct - the address you listed is complete and proper for mailing Form 4868 without payment via USPS. The reason there's no building number is that USPS has special routing agreements with federal agencies. When you include payment or use private carriers like FedEx/UPS, they need the specific building number because they don't have those same routing systems in place. One thing I'd add - if you're concerned about proof of delivery, consider sending it certified mail with return receipt. It only costs a few extra dollars but gives you peace of mind that it arrived on time. The postmark date is what matters for meeting the deadline, so as long as you mail it by April 15th (or whatever the current deadline is), you're covered even if it takes a few days to reach the IRS. Good luck with your extension!

Just want to add a quick warning - while you're sorting this out, make sure you respond to any IRS notices within the timeframes they specify, even if it's just to tell them you're disputing the issue. If you ignore notices completely, it can lead to escalation regardless of whether you're in the right or not. I learned this the hard way when I had a similar payment issue. I knew I had paid and figured it would sort itself out, so I ignored a couple of follow-up notices. Big mistake! That led to them sending me to collections even though I had proof of payment. Once you're in collections, everything gets more complicated and stressful.

I went through almost the exact same situation with payusatax.com last year! The key thing that finally worked for me was being extremely persistent with their customer service. Here's what I did: 1. Called them every single day at 8 AM sharp when they opened - I found that's when you're most likely to get through to an actual person rather than being stuck in their phone tree. 2. When I finally got someone on the phone, I immediately asked to speak to a supervisor about a "missing EFT reference number for IRS payment dispute." Using that specific language seemed to get me transferred to someone who actually knew what they were talking about. 3. I had my confirmation number, payment date, and credit card statement ready before I called. They were able to look up my payment in their system and provide the EFT reference number on the spot. The whole process took about two weeks of daily calls, but once I got the EFT number, I was able to provide it to the IRS and everything was resolved within a few days. Don't give up - the payment is definitely in their system somewhere, you just need to find the right person who can access it. Also, make sure you're calling payusatax directly and not going through any third-party sites that might look similar. Their real customer service number should be on your original payment confirmation email.

I went through something very similar with payusatax earlier this year and want to share what finally worked for me. After getting nowhere with their phone support, I found an old forum post suggesting to try logging into your payusatax account using the email address you used for payment rather than trying to search by confirmation number. When I did this, I was able to access a "Payment History" section that showed my EFT reference number - it was listed under a tab called "Federal Tax Payments" that I had completely missed before. The number was formatted differently than I expected (started with "EFT" followed by about 15 digits). If you can't remember which email you used or if you still can't access the account, there's another option: The IRS has a "Payment Verification" form (Form 3949-A) that you can submit along with your proof of payment. It takes longer to process, but they can manually research and apply your payment even without the EFT number. Also, make sure to call the IRS and request that they place a "payment tracer" on your account. This stops penalties from accruing while they investigate. You'll need your SSN, the payment amount, and the date you made the payment. They should be able to do this even if payusatax is being unresponsive.

I'm dealing with a very similar situation right now and this thread has been incredibly helpful! I made a payment through payusatax back in March and just got a notice saying the IRS never received it. Like others mentioned, payusatax customer service is completely unresponsive. One thing I wanted to add that might help others - if you're using a business credit card or bank account, sometimes the transaction details are more comprehensive than personal accounts. I called the business line at my bank and they were able to provide me with what they called an "ACH trace number" that wasn't visible in my online banking. Also, for anyone still struggling to reach the IRS by phone, I've found that calling right when they open (7am local time) significantly reduces wait times. I got through in about 20 minutes yesterday versus the 2+ hour waits I was experiencing calling later in the day. The agent I spoke with was actually very understanding about payment processor issues and said they see problems with payusatax fairly regularly. She was able to put a temporary hold on penalties while I work on getting the documentation sorted out. Don't give up - there are people at the IRS who want to help resolve these situations!