Has anyone filed Form CT-3-S for NY? I have an S-Corp (not an LLC) in New York but live in Connecticut, and I'm totally confused about what I need to file where. The NY website is so complicated!

This is exactly the kind of multi-state tax complexity that trips up so many LLC owners! Based on your situation, here are the key points: Since you're a Colorado resident performing all work in Colorado, that's where you'll owe state income taxes on the LLC income - regardless of where the LLCs are registered. Colorado will tax you on your worldwide income as a resident. For Delaware: Good news! Delaware generally doesn't tax income from LLCs that don't have physical presence in the state. You'll just need to pay the annual franchise tax ($300) to maintain registration. For New York: This is trickier. If your NY LLC has any nexus to New York (clients there, meetings there, property there), you might need to file NY returns. Even if you don't owe NY tax because you're not a resident, you may still need to file informational returns. One thing to watch out for: Make sure you're not creating unintended nexus by having business bank accounts, registered offices with mail forwarding, or conducting any business activities in DE or NY. I'd recommend consulting with a multi-state tax professional to review your specific situation, especially given the complexity of nexus rules. Each state interprets "doing business" differently, and you want to avoid any compliance issues.

Based on the current processing timeline, I'd recommend your friend submit the requested documents by April 30th at the latest. If they do that, they could potentially see a new DDD by June 15th. Another option is to check if they can upload the documents through the IRS online account portal rather than mailing them - as of March 1st, 2024, the IRS expanded their digital document submission options for certain verification requests.

As someone who's dealt with IRS verification requests before, I'd strongly suggest your friend respond ASAP with the requested documents. The key thing is that once the IRS flags a return for additional verification, any existing DDD gets canceled until they complete their review. For international students specifically, make sure to include a copy of your I-20 or DS-2019 along with the W2-G and 1099 forms - the IRS sometimes needs to verify your tax status. Also, send everything via certified mail so you have proof of delivery. The waiting is brutal, but being proactive with the documentation really helps speed things up!

This is exactly why I always tell people to use certified mail for anything tax-related! But for your current situation, you're not completely out of luck. Here's what I'd recommend: 1. **Request First Time Abatement** - If you haven't had penalties in the past 3 years, call the IRS and request "First Time Penalty Abatement" (FTA). This is often granted regardless of your ability to prove timely mailing. 2. **Document everything you remember** - Write down the exact date, time, post office location, description of the clerk, and any other details about your mailing. Even without a receipt, a detailed sworn statement can help. 3. **Check your bank records** - If you paid by check, the processing date might support your case that it was mailed timely. 4. **Contact the post office** - While they may not have records of your specific transaction, they might be able to provide a statement about their standard collection times from that date. The key is to be persistent and polite when dealing with the IRS. Many taxpayers successfully get penalties removed by explaining their situation clearly, especially for first-time issues. Don't give up - you have options!

I dealt with this exact same situation two years ago! The IRS claimed my payment was late even though I mailed it well before the deadline. Here's what ultimately worked for me: First, don't panic - you have several options even without a certified mail receipt. The most important thing is to act quickly and document everything you can remember about that day. **Immediate steps:** 1. **Call the IRS and request "First Time Penalty Abatement"** - If you haven't had penalties in the past 3 years, they often waive penalties regardless of proof. This is your easiest path to resolution. 2. **Gather any evidence you have** - Check your credit card or bank statements for the postage purchase, look for any other receipts from that day that place you near the post office, and write down every detail you remember (time, clerk description, etc.). 3. **Contact that specific post office** - While they won't have records of your transaction, they might provide a statement about their standard mail collection times for that date. **For your written appeal**, explain the situation clearly and mention that you specifically went early to ensure timely delivery, that you paid for proper postage, and that you watched the clerk place it in outgoing mail. The IRS does consider "reasonable cause" arguments, especially for taxpayers with good compliance history. The key is persistence - don't accept the first "no" if you get one. Many taxpayers successfully get these penalties removed by clearly explaining their situation and being polite but firm with IRS representatives.

I'm wondering if I should be worried. I made about $1800 babysitting last year and didn't report it... is the IRS gonna come after me now?

As someone who's been through this exact situation, I can confirm you're on the right track! Yes, you absolutely need to report that $2700 as self-employment income on Schedule C, even without a 1099. The IRS considers all income taxable regardless of whether you receive forms. A few tips from my experience: - Keep detailed records of all your babysitting-related expenses (mileage, supplies, etc.) - they add up quickly - You'll owe self-employment tax (about 15.3%) on your net profit after expenses - Since you earned over $600, you should consider making quarterly estimated tax payments going forward to avoid underpayment penalties next year - The family should have given you a 1099-NEC since they paid you over $600, but their oversight doesn't change your reporting obligation Don't stress too much - this is a common situation and as long as you report everything honestly, you'll be fine. The IRS actually appreciates when people proactively report income that might otherwise go unreported!

Has anyone noticed that FreetaxUSA sometimes doesn't recognize the supplemental tax withholding from RSUs correctly? I had to manually add my state withholding amounts because they weren't pulling in properly from my W-2 entry.

Great thread! I'm dealing with a similar RSU situation in FreetaxUSA. One thing I discovered that might help others - if you have RSUs that vested in multiple tranches throughout the year, FreetaxUSA has a "batch entry" feature in the Capital Gains section that can save you a lot of time. Instead of entering each sale transaction individually, you can group transactions with the same acquisition date and cost basis. This is especially helpful if you had quarterly vestings and multiple same-day sales. Just make sure your total proceeds and cost basis match what's on your consolidated 1099-B. Also, for anyone wondering about ESPP (Employee Stock Purchase Plan) transactions - those follow different rules than RSUs and have their own section in FreetaxUSA under "Other Income." Don't mix them up with your RSU reporting!