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I went through a very similar situation when I became trustee of my father's irrevocable trust that owned multiple rental property LLCs. One thing I learned the hard way is to also check your trust document for any specific provisions about inter-entity transactions or capital contributions. Our trust had a clause requiring written trustee resolutions for any transaction over $20,000 between trust-owned entities, which we almost missed. Even though I was the sole trustee, I still had to formally document the decision and keep it in the trust records for potential IRS audits. Also, if you go with the inter-company loan route (which I'd recommend based on Charlotte's advice), make sure to actually service the loan properly. The IRS has been known to recharacterize loans as distributions if payments aren't made consistently. Set up automatic transfers for the payments if possible to maintain the paper trail. The whole process was more complex than I expected, but documenting everything properly from the start saved us headaches later when we had to provide records to the IRS for an unrelated audit.
This is really helpful advice about checking the trust document for specific provisions - I hadn't thought to look for transaction thresholds that might require formal resolutions. Your point about actually servicing the loan properly is crucial too. I've seen situations where people set up these inter-company loans but then get lazy about the payments, which defeats the whole purpose from a tax perspective. Setting up automatic transfers is a great suggestion to maintain that paper trail. Thanks for sharing your experience with the IRS audit - it's good to know that proper documentation from the start actually pays off when they come looking!
As someone who recently went through a similar situation with my grandmother's irrevocable trust, I'd strongly echo the advice about the inter-company loan approach. We ended up going that route after initially considering the trust account method. One additional consideration that our attorney pointed out: if you have multiple beneficiaries of the trust, cycling money through the trust account can sometimes create unexpected income tax consequences for them, depending on how the trust's distributable net income is calculated. The inter-company loan keeps everything at the entity level and avoids potential complications with K-1 distributions to beneficiaries. Also, since you mentioned this is across two states, make sure to check if there are any state-specific requirements for related party transactions. Some states have additional disclosure or approval requirements for transactions between entities owned by the same trust. The $45,000 repair sounds urgent - I'd recommend moving quickly once you get your documentation in place. Property issues tend to get more expensive the longer they sit, and having a formal loan structure will give you a clear path for similar situations in the future.
That's a really important point about the distributable net income implications for beneficiaries - I hadn't considered how cycling money through the trust account could affect their tax situations. Since we do have multiple beneficiaries, the inter-company loan approach seems even more appealing now. You're absolutely right about the urgency of the repairs. We're already getting quotes from contractors and the roof situation is getting worse with the recent weather. Having a clear framework for these transfers will definitely help us handle similar situations more efficiently in the future. Thanks for the heads up about state-specific requirements - the properties are in Ohio and Pennsylvania, so I'll need to check both jurisdictions. Do you happen to know if there are any common red flags I should watch for in state regulations, or is this something I should definitely run by our attorney?
This is such a helpful thread! I'm in a similar boat - just started freelancing and trying to figure out all the tax stuff. One thing I'm still confused about: when you say the deduction is "limited to your business profit," does that mean your gross revenue or your net profit after all business expenses? For example, if my LLC brings in $50,000 in revenue but I have $20,000 in legitimate business expenses (equipment, software, etc.), would my health insurance deduction be limited to $30,000 or $50,000? Also, does anyone know if there's a difference between buying insurance through the marketplace vs. directly from an insurance company when it comes to this deduction? I've been looking at both options and the marketplace seems more complicated with all the subsidy calculations.
Great question! The deduction is limited to your NET profit after business expenses, not gross revenue. So in your example with $50,000 revenue and $20,000 in business expenses, your health insurance deduction would be capped at $30,000 (your net profit). As for marketplace vs. direct insurance purchase - there's no difference for the deduction itself. Both qualify equally. However, the marketplace can be more complex because of premium tax credits. If you qualify for subsidies through the marketplace, you can only deduct the amount you actually paid OUT OF POCKET after the credits are applied. So if your premium is $500/month but you get a $200 credit, you can only deduct $300/month. Many people find it easier to buy directly from insurers to avoid the subsidy complications, but you might miss out on significant savings if you qualify for marketplace credits. It's worth running the numbers both ways to see which gives you the better overall financial outcome.
I've been following this thread as someone who went through the same confusion last year! One additional consideration that hasn't been mentioned yet: timing matters for the deduction. You can only deduct premiums for months when you were actually self-employed and had no other health coverage available. So if you started your LLC mid-year or had employer coverage for part of the year, you'll need to prorate the deduction accordingly. Also, a practical tip: set up a separate business bank account if you haven't already, and pay your health insurance premiums from that account. It makes record-keeping much cleaner and provides a clear paper trail showing that your business income is what's funding the insurance. The IRS loves good documentation! One more thing - if you're planning to make estimated quarterly tax payments (which you probably should as a self-employed person), factor in the health insurance deduction when calculating those payments. It can significantly reduce what you owe, so don't overpay your quarterlies.
This is such excellent advice about timing and documentation! I hadn't thought about the proration aspect. Quick question - when you say "no other health coverage available," does that include things like short-term health plans or COBRA from a previous employer? I'm wondering if having COBRA available (but not taking it) would disqualify me from the deduction, similar to the spouse employer coverage rule that was mentioned earlier in the thread. Also, the separate business bank account tip is gold - I've been mixing personal and business expenses and it's already becoming a nightmare to track. Thanks for sharing your experience!
Don't forget about currency conversion fees! When I transferred my savings from Europe, my bank charged me an outrageous amount. Check if your bank has a partner bank in the US - sometimes they offer better rates. Or use a service like Wise or OFX for better exchange rates. I ended up losing almost $800 in fees and bad exchange rates because I didn't look into this first!!
One thing I haven't seen mentioned yet is the timing of when you transfer the money. If you're planning to transfer a large amount, consider spreading it across multiple smaller transfers over a few months rather than one big lump sum. This can help avoid triggering automated bank reporting systems that might flag large international transfers. Also, make sure to keep records of the exchange rates on the day you transfer - you might need this information for tax purposes later. The IRS uses specific exchange rates for different dates, and having your own documentation can save headaches if there are any questions about the USD equivalent value of your foreign earnings. Finally, if you haven't already, consider opening your US bank account first and letting it "season" with smaller deposits before doing the big transfer. Some banks are more comfortable with large international transfers when they already have a relationship with you.
This is really smart advice about spreading out the transfers! I'm actually dealing with a similar situation right now - have about $22k sitting in my German account that I need to bring over. Was planning to do it all at once but now I'm thinking maybe I should do it in chunks of like $7-8k each month? The point about exchange rates is something I hadn't thought about either. Do you know if there's a specific IRS source for historical exchange rates, or would screenshots from xe.com or similar sites be sufficient documentation? Also curious about the "seasoning" your account advice - how long would you recommend waiting between opening the account and doing the first transfer?
I went through this exact situation two years ago and can confirm that the consensus here is correct - your 401(k) distribution should be reported as ECI on Line 17a of Form 1040-NR. The key principle is that retirement distributions maintain the same tax character as the income that funded them. Since your contributions were made while you were working in the US (and thus earning effectively connected income), the distribution retains that ECI character even though you're now a nonresident alien. I initially made the mistake of reporting mine on Schedule NEC as non-ECI income, but after researching Revenue Ruling 79-388 and consulting with an international tax specialist, I filed an amended return to correct it. The IRS accepted the amendment without any issues. One important note: make sure to check if your tax treaty has any special provisions for retirement distributions. Some treaties provide for reduced withholding rates or other benefits that you don't want to miss out on. Also, keep detailed records of your employment history in the US, as this documentation supports the ECI classification if the IRS ever questions it. Don't let your accountant's advice in the comment below go unchallenged - this is a specialized area where many general practitioners get it wrong.
This is really helpful, thank you! I'm in a similar situation and was getting confused by different advice. When you filed your amended return, did you have to pay any additional tax or penalties? I'm worried about the timing since I already filed my original return with the distribution on Schedule NEC. Also, do you happen to know if there's a specific form or statement I should include with the amended return to explain the correction?
As someone who recently went through this exact situation, I can confirm that your 401(k) distribution should indeed be reported as ECI on Line 17a of Form 1040-NR. The reasoning everyone has shared here is spot-on - the distribution retains the character of the income that funded it. I made the same mistake initially and reported mine on Schedule NEC, but after doing more research and finding Revenue Ruling 79-388, I realized my error. The ruling makes it clear that retirement plan distributions to former employees maintain their ECI status even after the individual becomes a nonresident alien. One thing I'd add is to be extra careful about the withholding. Your 401(k) plan administrator may have withheld taxes at the standard 30% nonresident rate, but since this is ECI, you might be entitled to a refund depending on your other income and deductions. Make sure to calculate your actual tax liability properly. Also, don't forget to check if your home country's tax treaty has any provisions about retirement distributions - some treaties allow for reduced withholding or provide other benefits that could save you money. The tax treaty analysis can be complex, but it's worth investigating since it could significantly impact your final tax bill.
This is exactly the kind of detailed guidance I was hoping to find! I'm dealing with this same situation right now and have been going back and forth on the ECI vs non-ECI classification. Your point about the withholding is really important - my plan administrator did withhold at 30%, so I'll definitely need to calculate whether I'm due a refund. Quick question: when you mention checking the tax treaty provisions, did you find that most treaties actually have specific language about 401(k) distributions, or do they fall under more general retirement/pension clauses? I'm from Canada and trying to figure out if the US-Canada treaty has anything that would apply to my situation specifically. Also, did you end up needing to file any additional forms beyond the 1040-NR when you corrected your reporting from Schedule NEC to Line 17a?
Lindsey Fry
Maxwell, I totally understand your frustration with that vague IRS letter! I went through something similar with my own RMD penalty situation about 6 months ago. Those acknowledgment letters are intentionally generic - they're basically just saying "we received your paperwork and it's in the system." The good news is that you did everything correctly by filing Form 5329 with an explanation letter and paying the penalty upfront. In my experience, when you handle it this way, the IRS rarely comes back with additional issues. They're mainly looking to see that you've acknowledged the mistake, calculated the penalty correctly (which sounds like you did at $875), and taken steps to prevent it from happening again. I'd recommend waiting at least 12 weeks from your original submission date before getting concerned. The IRS is still dealing with processing backlogs, and RMD penalty cases aren't high priority for them since you've already paid. If you don't hear anything after 3 months, that's usually a sign that your case was processed successfully and closed. Also, don't beat yourself up too much about missing the RMD when your advisor retired suddenly - that kind of unexpected situation is exactly why the IRS sometimes grants penalty waivers if you can demonstrate reasonable cause!
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Ellie Perry
ā¢Thanks Lindsey, that's really reassuring to hear from someone who's been through this! The 12-week timeline gives me a concrete expectation to work with instead of just wondering indefinitely. I'm about 6 weeks in now since I originally submitted everything, so I guess I'm halfway through the waiting period. It's good to know that paying upfront and including the explanation letter puts me in a better position - I was second-guessing whether I should have tried to argue for a waiver instead of just paying immediately. But it sounds like being proactive about payment actually helps move things along faster.
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Logan Stewart
I'm going through almost the exact same thing right now! Filed my Form 5329 about 7 weeks ago for a missed RMD (also due to advisor issues - mine moved firms and the transition got messy). Got that same frustratingly vague acknowledgment letter that tells you absolutely nothing useful. Reading through all these responses is actually making me feel much better about the situation. It sounds like this is just how the IRS operates with Form 5329 submissions - they send the generic "we got it" letter first, then take their sweet time processing everything before sending any kind of final resolution. The timeline everyone's mentioning (8-12 weeks) seems pretty consistent across different people's experiences. I'm trying to be patient but it's hard when you're wondering if you're going to get hit with additional penalties or complications. At least I know I'm not the only one dealing with this kind of confusing communication from the IRS!
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