I had the exact same problem last year with over 80 transactions from my E*TRADE account. After trying several free converters that either crashed or produced corrupted TXF files, I found that the key is making sure your CSV is properly formatted BEFORE conversion. Here's what worked for me: First, open your CSV in Excel and verify that all required fields are present - transaction date, symbol, quantity, buy/sell price, and acquisition date. Remove any summary rows or extra headers that might confuse the converter. Make sure dates are consistent (I used MM/DD/YYYY format throughout). Then I used the TaxACT CSV to TXF converter (free version handles up to 500 transactions) which worked flawlessly. The resulting TXF file imported into TurboTax without any errors. Just make sure to backup your original CSV first in case you need to make adjustments. One gotcha - if you have any corporate actions like stock splits or mergers, you'll need to adjust those transactions manually in your CSV before conversion. The automated converters don't handle complex corporate actions well.

I've been dealing with this exact same issue! After trying multiple approaches mentioned here, I ended up using a combination method that worked perfectly. First, I cleaned up my Schwab CSV export in Excel - removed extra headers, standardized date formats to MM/DD/YYYY, and added a "Type" column to clearly mark Buy/Sell transactions. Then I used the free version of CSV2TXF converter (found it on SourceForge) which handled my 150+ transactions without any issues. The key was making sure my CSV had these exact column headers: Date, Action, Symbol, Quantity, Price, Commission, Total. Before importing to TurboTax, I opened the generated TXF file in a text editor to spot-check a few transactions - this caught one formatting issue where my commission column had some blank cells that needed to be filled with zeros. The whole process took about 2 hours including cleanup, but it beat manually entering everything. My TurboTax import went smoothly and all the gain/loss calculations matched my broker statements. Definitely recommend the "clean CSV first, then convert" approach over trying to find a converter that can handle messy data.

I think people often confuse tax RESIDENCY rules (for income tax filing purposes) with Social Security/Medicare tax obligations. They're governed by different sections of the tax code! Even some tax preparers get this wrong. I've seen software engineers on EADs mistakenly told they're exempt when they're not. Always check IRS Publication 519 "U.S. Tax Guide for Aliens" - it covers this topic specifically.

Great thread with lots of helpful info! I just wanted to add that if you're unsure about your specific situation, you can also check Box 3 (Social security wages) and Box 5 (Medicare wages) on your most recent pay stub or W-2. If your employer is withholding these taxes, those boxes should show your wages subject to these taxes. Also, once you do get your actual Green Card, nothing changes regarding FICA taxes - you'll continue paying Social Security and Medicare taxes just like you are now with your EAD. The transition is seamless from a payroll tax perspective. One more tip: keep good records of all your Social Security contributions during your EAD period. When you eventually apply for Social Security benefits (whether retirement, disability, etc.), all these contributions will count toward your benefit calculation, regardless of whether they were made before or after you got your Green Card.

Been through this confusion before! One thing to watch out for - make sure you're using the correct paper size if you're mailing physical forms. The IRS is super picky about this. They want the official forms printed on 8.5 x 11 paper with no modifications to the layout or scaling. I learned this the hard way when they rejected my forms and almost hit me with a penalty.

Just to add another perspective - if you're really pressed for time and worried about getting everything right, consider reaching out to a local CPA or tax preparer who can handle this quickly. Many of them offer W-2/W-3 preparation services for a reasonable fee (usually $50-150 for a small S corp) and can often turn it around same-day or next-day. They'll handle all the form requirements, filing deadlines, and can even e-file for you. Sometimes it's worth paying a professional to avoid the stress and ensure compliance, especially when you're cutting it this close to the deadline.

I totally get your stress about this situation! 😊 As someone who's been through a similar experience with side income, I wanted to share what helped me navigate this without losing my mind. First off, you're absolutely doing the right thing by asking about this now. The IRS actually has a lot of respect for people who proactively try to comply, so you're already on the right track! Here's what I learned when I was in your shoes: • Yes, you'll need to report income over $400 on Schedule C (self-employment) • Start tracking everything going forward - even a simple phone note works • Save receipts for ANY babysitting-related expenses (gas, snacks for kids, activities, etc.) • Consider setting aside 20-25% of each payment for taxes One thing that really helped ease my anxiety was using the IRS Free File software (available on IRS.gov) - it walks you through everything step by step and is specifically designed for situations like yours. Also, since you're caring for your mom, definitely look into caregiver tax credits when you file. There might be deductions available that could help offset some of what you owe on the babysitting income. The most important thing to remember: the IRS isn't trying to "catch" people who are making honest efforts to comply. You're being responsible by asking these questions, and that counts for a lot. Take it one step at a time - you've absolutely got this! 💪 Have you been able to estimate roughly how much you've made babysitting so far this year?

Hey Yuki! 💙 I can really feel the stress in your post, and I want you to know that you're definitely not alone in this situation! I actually went through something very similar when I started doing some occasional house-sitting for extra income while also caring for my elderly father. First, let me echo what others have said - you're absolutely doing the right thing by asking these questions now rather than ignoring the situation. That shows real responsibility and good faith effort, which the IRS genuinely appreciates. Since you're making $150-200/week, you're definitely over the $400 annual threshold, so yes, you'll need to report this as self-employment income on Schedule C. But here's what helped me get through the stress of it all: • Start simple - even just a note in your phone with date/amount for each babysitting session going forward • Keep track of ANY expenses related to the work (gas to their house, snacks/activities for kids, even educational materials) • The free IRS VITA program can help you file if your income qualifies - they're specifically trained for situations like this • Since you're caring for your mom, definitely explore caregiver tax credits that might help offset what you owe What really helped my anxiety was calling the IRS Taxpayer Assistance line (1-800-829-1040). I was terrified to call, but the person I spoke with was incredibly patient and walked me through exactly what I needed to do. They're there to help, not to intimidate! One last thing - you have until April 15th to get this sorted, so there's no need to panic. Take it one step at a time. You're clearly a caring, responsible person who's working hard to support your family. You've got this! 🌟

This thread has been absolutely amazing! I just went through a very similar situation last year and wish I had found this discussion earlier. I owned a home for 17 years - lived in it as my primary residence for 13 years, then rented it out for 4 years before selling. Like many others here, I initially calculated my exclusion using the proportional method (13/17) and was expecting a huge tax bill. After reading through all these experiences, I realized I had been overthinking it completely. Since my rental period came AFTER my primary residence years, those 4 rental years didn't count as "non-qualified use" for the exclusion. I was able to exclude almost my entire $140k gain except for the depreciation recapture on the $26k I had claimed during the rental years. The depreciation recapture at 25% cost me about $6,500 instead of the $35k+ I was originally planning to set aside for taxes. What a relief! I ended up using one of the AI tools mentioned earlier in this thread to double-check my calculations, and it was incredibly helpful in walking me through the proper application of these rules. The tool even helped me identify some home improvements I had forgotten about that further reduced my taxable gain. For anyone still reading through this thread who's in a similar situation - definitely don't assume the proportional calculation is correct. The actual tax law is much more favorable for conversions from primary residence to rental. Just make sure you get professional confirmation before filing!

This has been such an enlightening discussion! I'm currently dealing with a property sale where I lived in the home for 9 years as my primary residence, then rented it for 2 years before selling last month. Reading through everyone's experiences here has been incredibly reassuring. I was initially calculating based on a 9/11 ratio (about 82% exclusion), but now I understand that those 2 rental years after my primary residence period don't count as "non-qualified use" under the current tax rules. I claimed about $11k in depreciation during those rental years, so it looks like I'll only owe the 25% recapture tax on that amount (roughly $2,750) rather than the much larger capital gains tax I was expecting to pay on a significant portion of my $75k gain. What really strikes me is how this favorable rule for post-residence rental periods isn't widely known. I've talked to several people who went through similar situations and none of them were aware of this distinction. It seems like the proportional calculation is what most people default to because it feels logical, but the actual tax law is more generous than that. I'm definitely going to look into some of the tools mentioned throughout this thread to get confirmation before I file. With the peace of mind that would provide, it seems worth it to make sure I'm applying these rules correctly and not leaving money on the table or making any errors. Thanks to everyone who shared their knowledge and real-world experiences here - this community discussion has been incredibly valuable!