Thanks everyone for all the detailed advice! This is exactly what I needed. Just to clarify a few things based on what I'm reading: 1. My S-Corp should reimburse me for the laptop and software I paid for personally, then deduct those on the 1120-S 2. For my cell phone, I need to document the 70% business use and have the S-Corp reimburse only that portion 3. I should set up a formal accountable plan for ongoing reimbursements Quick follow-up question - if I get reimbursed by my S-Corp now (in April) for expenses I paid in January-March, does that still count for the 2024 tax year or does it become a 2025 deduction? I want to make sure I'm handling the timing correctly. Also really appreciate the warnings about reasonable salary and health insurance - I definitely need to review those areas too!

Just want to add another perspective here - I went through this exact situation with my S-Corp last year and made some mistakes that cost me. One thing I didn't see mentioned is the importance of getting your corporate bylaws and operating procedures documented properly BEFORE you start doing reimbursements. The IRS can challenge reimbursements if they don't follow proper corporate formalities. I had to go back and create board resolutions approving my expense reimbursement policy retroactively, which looked suspicious. Better to have everything documented upfront. Also, be really careful with that home office deduction. If your S-Corp is going to reimburse you for home office expenses, you need to establish a formal rental agreement between yourself and your corporation. The rent you charge should be reasonable for your area - I used comparable office space rates in my neighborhood as justification. One last tip - consider getting a separate business credit card for all S-Corp expenses going forward. It makes tracking so much easier and eliminates the need for most reimbursements. The corporation pays the bill directly and you never have to worry about the personal vs business expense classification issues.

For someone new to crypto taxes like yourself, here are the key points to remember: 1. **Yes, you need to report your crypto activity.** There's no minimum threshold - even $1 in gains needs to be reported. The IRS asks about crypto transactions right on Form 1040. 2. **What matters is your actual gains/losses, not withdrawal amounts.** If you invested $2700 and withdrew $1250, you need to calculate the difference between what you paid for the crypto you sold versus what you sold it for. 3. **For tax withholding,** I'd recommend setting aside 25-30% of any gains if you're actively trading (short-term rates). If you held for over a year, long-term capital gains rates are much lower (0%, 15%, or 20% depending on income). 4. **Start tracking everything now.** Every crypto-to-crypto trade, every sale, every purchase - it all needs to be documented. Your exchange should have transaction histories you can download. The good news is that if you had losses on some trades, those can offset your gains. But you absolutely need to report everything to stay compliant with the IRS.

One thing I'd add that hasn't been mentioned yet - make sure you understand the "wash sale" implications for crypto. While the traditional wash sale rule doesn't technically apply to crypto (since it's treated as property, not securities), the IRS has been signaling they may crack down on this. A wash sale is when you sell crypto at a loss and then buy the same or substantially identical crypto within 30 days. If you're doing this to harvest tax losses while maintaining your position, be aware this could be scrutinized. Also, don't forget about state taxes! Some states have no capital gains tax, but others will tax your crypto gains at their regular income tax rates. This can add significantly to your tax bill depending on where you live. For your $2700 investment with $1250 withdrawn, focus on calculating the actual cost basis of what you sold versus the sale price. The total amounts invested/withdrawn don't tell the whole story - it's all about the specific transactions and their timing.

As a new community member, I want to express my gratitude for this incredibly comprehensive discussion! I've been hesitant to get into T-Bill trading specifically because I was intimidated by the tax implications, but this thread has transformed what seemed like an impenetrable wall of complexity into a manageable step-by-step process. The evolution of this discussion from @Tami Morgan's original question to a full guide covering everything from basic reporting principles to advanced elections and tracking systems is remarkable. What I find most valuable is how everyone has shared not just the "what" but the "how" - actual TurboTax navigation steps, specific IRS code references, and real-world tools that have worked. I'm particularly intrigued by the combination of approaches people have successfully used. The idea of using AI analysis tools for complex document review, combined with traditional record-keeping and direct IRS confirmation when needed, seems like a robust strategy that covers all bases. As someone just starting out, I'm planning to implement several suggestions from this thread: setting up the tracking spreadsheet @Amelia Martinez described, keeping the de minimis thresholds in mind for smaller trades, and using the clear TurboTax categorization approach @Nia Johnson outlined. Having this roadmap removes so much of the uncertainty that was holding me back. This thread perfectly exemplifies why community knowledge-sharing is so powerful - thank you all for creating such a valuable resource!

As a new member of this community, I want to add my heartfelt thanks for this incredibly detailed and practical discussion! I've been putting off T-Bill investments for months specifically because I was overwhelmed by the tax reporting complexity, but this thread has given me the confidence to finally move forward. What I find most impressive is how this conversation has covered every angle - from the fundamental tax principle that market discount equals interest income, to specific TurboTax navigation steps, to advanced election strategies for frequent traders. The real-world experiences everyone has shared, especially the tool recommendations and IRS confirmation stories, provide exactly the kind of validation a newcomer needs. I'm particularly grateful for @Nia Johnson's step-by-step TurboTax instructions and @Theodore Nelson's explanation of the de minimis election. Having those specific procedural details removes so much guesswork. The tracking system suggestions from @Amelia Martinez are also going straight into my implementation plan. As someone just starting out, I'm planning to begin with small T-Bill positions while implementing the organization and tracking methods discussed here. The combination of good record-keeping, understanding the core tax principles, and having reliable tools available seems like the perfect foundation for building confidence in this investment space. Thank you all for creating such a comprehensive resource - this thread will definitely be my go-to reference as I navigate my first T-Bill transactions!

Something similar happened to my wife last year. Turned out someone had her SSN and attempted to file a return. The most important thing is to ACT FAST. The longer this goes unresolved, the more complicated it can get. When we called the IRS, they put a special marker on her account and gave us a PIN we need to use for filing taxes going forward. It protects against anyone trying to file with her SSN again. You should ask about this when you talk to them!

I went through something very similar about 6 months ago - that sinking feeling when you see something unexpected in your IRS account is awful! Since you confirmed it's showing up in your official IRS online account, this is definitely legitimate and needs immediate attention. Here's what worked for me: I filed my legitimate return first thing the next morning (even though I was worried about the verification issue), then immediately called the IRS. When I got through, I explained that I had a verification notice in my online account but had never failed to file. The agent was actually really helpful and walked me through the process. In my case, someone had attempted to file a return with my SSN but it got flagged by their fraud detection system before processing. The "verification of non-filing" notice was basically the IRS asking me to confirm I hadn't actually filed yet, which cleared up the confusion. The whole thing took about 2 weeks to resolve, and I did get my refund (just delayed). The agent also set me up with an IP PIN for future protection. Don't let the stress eat you up - this is more common than you'd think and the IRS has good procedures for handling it!

When I had both W2 and 1099 income, I learned that if you physically go to an IRS Taxpayer Assistance Center, they sometimes offer free tax prep services if your income is below certain limits. You need to call to make an appointment though. Also check if your local library or community center offers VITA (Volunteer Income Tax Assistance) services. They'll do your taxes for free including Schedule C if your income is under about $60k.

Just to add another perspective - I had a very similar situation with W2 income from two states plus freelance 1099 income. After trying multiple free options, I ended up going with H&R Block's online service. They have a mid-tier option that handles both W2 and Schedule C filing for around $50, which was way cheaper than their in-person service. What really helped me was their interview-style questions that walked me through the multi-state income reporting step by step. They automatically calculated how much state tax I owed to each state based on where I earned the income, which was exactly what I needed for my Colorado/Nevada situation. The key thing I learned is that while you definitely can't split your filing like you originally asked, there are affordable options beyond the expensive TurboTax upgrades. Don't feel like you're stuck paying premium prices just because you have mixed income sources!