Just wanted to share my experience as someone who went through IRA withdrawals as a non-resident alien last year. The key thing I learned is that timing matters a lot - if you contributed to your IRA while you were a US tax resident (which sounds like your case with the H1B), those contributions may be treated differently than if you had contributed as a non-resident. I'd strongly recommend getting professional help for your specific situation. The treaty benefits with India can be significant, but the application process is tricky. My financial institution initially applied the full 30% withholding even though I was entitled to the reduced treaty rate. I had to file Form 1040NR to get the overwithholding back, which took about 8 months. One important tip: make sure to file your W-8BEN with your IRA custodian BEFORE you make any withdrawals. Even if they mess up the withholding initially, having it on file helps establish your treaty claim later. Also, keep detailed records of when you made each contribution and your tax residency status at those times - the IRS may ask for this information. For HSA withdrawals, the rules are even more complex because of the medical expense qualification requirements. You'll want to be very careful about documentation there.

I've been following this thread closely as I'm in a very similar situation - non-resident alien with both IRA and HSA accounts from my time on an H1B visa. The information shared here has been incredibly helpful, especially about the India tax treaty benefits. One additional point I'd like to add based on my research: if you're planning multiple withdrawals over time, consider the timing carefully. The IRS looks at your tax residency status on the date of each distribution, not when the contributions were made. So if your residency status changes during the year, it could affect the tax treatment of different withdrawals. Also, for those dealing with HSA withdrawals as non-residents, I found that keeping detailed records of all medical expenses (even those incurred abroad) is crucial. The IRS Publication 502 lists qualifying medical expenses, and many expenses incurred overseas do qualify as long as they meet the US criteria. However, you'll need proper documentation and potentially currency conversion records. Has anyone dealt with state tax implications on these withdrawals? Some states continue to tax former residents on retirement account distributions even after you've moved abroad, which could add another layer of complexity to consider.

A lot of good advice here but something important is being missed - the SECURE Act changed the RMD age from 70½ to 72, and then SECURE 2.0 changed it again to 73 for people born 1951-1959. Your father being 79 now (born around 1945?) would have hit RMD age under the old rules. Also, depending on how small the Simple IRA is, you might want to consider a full withdrawal to simplify things going forward, especially if managing annual RMDs will be challenging with his condition.

This is a challenging situation but you're taking the right steps to get your father back into compliance. Based on my experience helping elderly clients with similar issues, here are a few additional considerations: 1. **Documentation timing is crucial** - Get a letter from his doctor that specifically states when his cognitive decline began affecting his ability to manage financial affairs. This will be key for the penalty waiver requests. 2. **Consider the timing of distributions** - Rather than taking all missed RMDs immediately, you might want to spread them across 2024-2025 to manage the tax impact, while still filing the 5329 forms for each missed year. 3. **State tax implications** - Don't forget to check if your state has any additional requirements or penalties for missed RMDs. 4. **Future planning** - Once you get this resolved, consider setting up automatic distributions from the IRA to prevent future missed RMDs, especially given his condition. The IRS really is understanding in these situations when there's documented medical cause. Focus on getting that medical documentation first, then work through each year systematically. A tax professional experienced with elder financial issues would be a good investment here given the complexity and multiple years involved.

One thing to keep in mind when calculating your basis - the IRS has a "safe harbor" provision for home improvements that might help with your documentation concerns. If you can show that similar improvements in your area during the same time period cost within a reasonable range of what you're claiming, that's generally acceptable even with some missing receipts. Since you mentioned getting quotes from contractors, those estimates can actually be really valuable for establishing the fair market value of materials used, even though you can't include labor. For example, if a contractor quoted $50k total for a kitchen remodel and you know labor typically represents 60-70% of renovation costs, you could reasonably estimate that $15-20k worth of materials were involved. Also worth noting - given your substantial gain even after the primary residence exclusion, you might want to consider if any of the work qualifies for energy efficiency tax credits that could offset some of your tax liability. Things like new windows, HVAC systems, or solar installations might qualify for additional benefits beyond just adding to your basis.

I went through something very similar when I sold my house last year after doing tons of DIY work over a decade. Here's what I learned from working with my CPA: You absolutely cannot include your labor value, but don't overlook these often-missed items that CAN be added to your basis: - Permits and inspection fees for all those projects - Architectural plans or design consultations you paid for - Specialty tools you had to buy specifically for permanent improvements (like a tile saw for bathroom work) - Delivery fees for materials - Dumpster rentals for construction debris - Any structural engineering reports if you had foundation work done For missing receipts from older projects, my accountant had me create a detailed log with project dates, square footage affected, and reasonable material cost estimates based on current prices adjusted for inflation. Home Depot and Lowe's can sometimes provide purchase history going back several years if you had a Pro account or used the same credit card consistently. One thing that really helped was finding old permits in our city's online database - even projects I'd forgotten about were documented there with dates and scope descriptions that helped justify our improvement timeline. Given your $1M+ gain situation, definitely consider hiring a tax professional who specializes in real estate transactions. The cost will be worth avoiding potential audit issues with such large numbers involved.

Has anyone had success claiming both the American Opportunity Credit AND having a child with partially taxable PELL grants? My tax software is giving me warnings about "double-dipping" but doesn't explain how to fix it.

Just wanted to add my experience dealing with this exact situation last year. My son received a PELL grant that covered his tuition plus gave him about $3,000 extra for living expenses. The tricky part was that even though he's my dependent and I provide all his support, HE had to file his own tax return to report the $3,000 as taxable income (since it wasn't used for qualified education expenses). This was confusing at first because I thought dependent income always went on the parent's return. What helped me understand it: The PELL grant belongs to your son, not you. So any taxable portion is his income to report. You still get to claim him as your dependent though, which means he can't claim his own personal exemption. Also, make sure to get Form 1098-T from his college - it shows the tuition paid and grants received, which helps you figure out what portion of the PELL grant was used for qualified vs non-qualified expenses. This form is crucial for both his return and yours if you're claiming education credits.

I went through this exact situation a couple years ago and I know how overwhelming it feels right now, but you absolutely can get through this! The March 6th deadline actually gives you plenty of time if you start taking action now. Here's what I learned from my experience: **Get your transcripts first:** Like everyone's saying, request your wage and income transcripts online at irs.gov/transcripts for 2019-2022. This is absolutely essential - it shows you exactly what income the IRS already has on file and makes preparing your returns so much easier. Mine came within about a week. **Check if you even need to file for all years:** Look up the filing thresholds for each year. I discovered that for one of my "missing" years, my income was actually below the requirement, so I just had to send an explanation letter instead of a full return. **Don't let them calculate for you:** Whatever you do, don't miss the deadline and let them determine your taxes based on third-party info. They won't include any deductions, credits, or even the standard deduction - you'll end up owing way more than you actually should. **Document your hardships:** Since you mentioned going through rough personal times, gather any documentation of health issues, depression, family crises, etc. I was able to get over $1,000 in penalties waived through reasonable cause abatement by showing I had documented mental health struggles during my non-filing period. **Consider professional help:** I tried doing it myself at first but honestly, hiring a tax preparer for about $200-250 per year was worth every penny. They caught deductions I would have missed and helped with the penalty process. The situation feels scary now, but once you get those transcripts and start working through it systematically, it becomes much more manageable. You've got this!

I understand this feels incredibly overwhelming right now, but you're getting some excellent advice here and you have enough time to handle this properly before March 6th. Here's what I'd focus on as your immediate next steps: **This week:** Get your wage and income transcripts from irs.gov/transcripts for each year (2019-2022). This is absolutely critical and will show you exactly what the IRS expects to see on your returns. **While waiting for transcripts:** Start gathering any documents you can find - old emails, contact former employers for W-2s, check bank statements. Don't stress if you can't find everything; the transcripts will fill in most gaps. **Important reality check:** Since you mentioned going through depression during those years, you should definitely look into reasonable cause penalty abatement once everything is filed. Multiple people here have saved hundreds or thousands in penalties by documenting their mental health struggles - this could make a real difference for you financially. **Don't go it alone:** Given that you're dealing with 4 years and your situation sounds complex, seriously consider hiring a tax professional. Yes it costs money upfront, but they can maximize your deductions and handle the penalty abatement process. The peace of mind alone is worth it when you're already stressed. Most importantly - don't let the March deadline pass and have them calculate your taxes for you. They won't include any deductions or credits, so you'll owe way more than necessary. You mentioned needing this refund for bills, so I get the urgency. Even if it gets applied to past balances, resolving this properly prevents much bigger problems later. Take it one step at a time and start with those transcripts!