Don't forget about the wash sale rule if you're trying to do tax loss harvesting! If you sell investments at a loss and buy "substantially identical" securities within 30 days before or after the sale, you can't claim the loss for tax purposes.

Great question about ESPP gains and tax loss harvesting! Yes, you can definitely use your regular brokerage losses to offset ESPP capital gains - the IRS treats all capital gains and losses the same regardless of source. However, make sure you're calculating your ESPP gains correctly. With a 15% discount and immediate sale after the holding period, you likely have both ordinary income (the discount portion that should appear on your W-2) and capital gains/losses (any price movement from purchase to sale). Only the capital gains portion can be offset by your other investment losses. Since you have $11,000 in losses versus $8,400 in ESPP gains, you should be able to fully offset those gains and still have $2,600 in losses to carry forward or offset other gains. Just watch out for the wash sale rule if any of your losses involve the same company stock as your ESPP!

Has anyone used TurboTax to claim home office deductions like this? The software kept giving me warnings when I tried to deduct my home office renovation costs last year.

I went through something very similar in 2020-2021 when I claimed renovation expenses for my home office setup. The key distinction the IRS agent explained to me is that major renovations like what you described are typically considered "capital improvements" rather than startup costs or regular business expenses. Capital improvements need to be depreciated over time (usually 39 years for home office improvements) rather than deducted all at once. The fact that you deducted the full $18,500 in one year as startup costs is likely what triggered their attention, especially combined with zero income. When I dealt with my situation, I had to file an amended return using Form 8829 to properly categorize the renovation as a capital improvement and start depreciating it. The IRS was actually pretty reasonable about it once I showed I was genuinely trying to run a business and had documentation of my business activities (even though I wasn't profitable yet). My advice: Don't panic, but do take this seriously. Gather all your receipts, any evidence of business activity (marketing efforts, business registration, etc.), and consider consulting a tax professional before responding. The IRS agent is likely just trying to understand if this is a legitimate business expense that was incorrectly categorized rather than looking to penalize you.

Quick question - I'm in a similar boat and wondering if I should just use TurboTax or something to catch up on my unfiled years? Anyone tried that route?

I went through this exact situation last year - 7 unfiled returns! After reading all the advice here, I ended up going with an Enrolled Agent and it was absolutely the right choice. Here's what I learned: the main advantage of an EA isn't just filing the returns, it's dealing with all the complications that come with being behind. When the IRS started sending me notices about penalties and interest, my EA handled all of that correspondence. She also knew exactly which forms to use for prior year filings and caught several issues that would have caused problems later. The cost was higher than a regular preparer (about $300 per return vs $150), but she saved me way more than that in penalties she got waived. Plus, she set up a payment plan for the taxes I owed, which I had no idea I could even do. My advice: definitely go with an EA for multiple unfiled years. The peace of mind alone is worth it when you're dealing with the IRS on back taxes.

Has anyone used TurboTax for this? I'm trying to figure out where to enter this in the software and it's confusing me.

Great question! I went through this same confusion a couple years ago. You're right to be careful about double-reporting. When you use Form 8814 to report your child's investment income on your return, you do NOT need to report those same dividends as nominee dividends on Schedule B. The key thing to understand is that Form 8814 is specifically designed to handle this situation. By filing Form 8814, you're making an election to include your child's unearned income on your return instead of filing a separate return for them. This means those dividends essentially become "your" income for tax purposes. Nominee dividends on Schedule B are only used when you receive income that belongs to someone else AND you're not including that person's income on your tax return. Since you're using Form 8814, you ARE including your daughter's income on your return, so the nominee dividend treatment doesn't apply. Just make sure you have all the dividend statements that show your daughter as the recipient, and report those amounts correctly on Form 8814. The IRS will match up the 1099-DIV forms with what you report on Form 8814. With $230 in dividends, you're well under the $1,150 threshold where it would start affecting your taxes, so this should be pretty straightforward once you get Form 8814 filled out correctly!

Quick tip from someone who's been through this: Make sure you're including Form 843 specifically for the FICA refund request, not just an amended return. Many international students don't realize these are separate processes. Also, attach a copy of your I-94, visa documentation, passport ID page, and a letter from your international student office confirming your visa/OPT status. I had success when I included a cover letter clearly stating "FICA TAX REFUND REQUEST - NONRESIDENT ALIEN ON F-1 VISA" in bold at the top.

I went through this exact same nightmare last year and want to share what finally worked for me. After my first submission disappeared into the IRS black hole, I took a multi-pronged approach: 1. Used certified mail with return receipt for my second submission (as others mentioned) 2. Called the Taxpayer Advocate Service after 20 weeks of waiting - they were incredibly helpful and actually located my original submission stuck in processing 3. Made sure I had ALL required documents: Form 843, Form 8843, copy of I-94, visa pages, I-20/DS-2019, employer letter confirming FICA withholding, and university letter confirming F-1 status The key thing the Taxpayer Advocate told me was that FICA refunds for nonresident aliens go through a manual review process that's completely separate from regular refunds, which is why it takes so much longer. They also confirmed that having duplicate submissions won't hurt you - they'll just process whichever one they find first. My refund ($2,850) finally came through about 6 weeks after the Taxpayer Advocate got involved. Don't give up - this money is rightfully yours and they will eventually process it correctly!