I'm dealing with a very similar situation and this thread has been incredibly enlightening! I have about $16k in COBRA payments from a 5-month gap between jobs, and I'm currently in final negotiations with my new employer. Based on what I'm reading here, it sounds like the magic is in getting the language right in the offer letter to establish this as a qualified health benefit rather than taxable compensation. I'm particularly interested in the Section 105 plan approach that Sean mentioned - that "transition period" concept seems like exactly what I need. My question is about implementation timing: if I get the right language in my offer letter this week, how quickly can most companies actually process the reimbursement once I start? I'm hoping to get these COBRA costs off my credit card sooner rather than later. Also, for those who successfully negotiated this, did you find that having a specific dollar amount helped or hurt during negotiations? I'm wondering if I should present it as a lump sum or break it down by monthly COBRA payments. The taxr.ai tool sounds promising too - might upload my documents tonight to see what specific language gaps they identify before my final negotiation call tomorrow.

As someone who went through a similar situation with COBRA reimbursements, I wanted to share a few practical tips that might help others navigating this process. First, timing is absolutely critical - you need to get the right language in your offer letter before signing, not after you start. I learned this the hard way when my first employer just treated it as taxable income because we didn't establish the proper framework upfront. Second, be prepared to educate your employer's HR team. Many smaller companies haven't dealt with Section 105 health reimbursement arrangements before, so having specific references to IRS publications (like Pub 15-B) and being able to explain how it benefits both parties really helps move the conversation forward. Third, document everything meticulously. Keep all your COBRA election notices, payment confirmations, and bank statements organized. The IRS requires proper documentation for these arrangements, and having everything ready shows you're taking this seriously. Finally, consider the company's size and benefits sophistication when setting expectations. Larger companies with dedicated benefits teams can usually handle these arrangements more easily, while smaller firms might need more time and hand-holding but often have more flexibility to make quick decisions. The key is framing this as a legitimate health benefit transition rather than trying to avoid taxes on what would otherwise be compensation. When positioned correctly, most employers are surprisingly receptive to helping with healthcare continuity.

Just wanted to add another perspective here - I work with disability benefits and see this situation frequently. A few key points that might help: 1. **SSI vs. SSDI distinction**: Make sure it's actually SSI (Supplemental Security Income) and not SSDI (Social Security Disability Insurance). SSI is needs-based and tax-exempt, while SSDI could be partially taxable if her total income exceeds certain thresholds. 2. **Support calculation tip**: When calculating the 50% support test, include the fair rental value of her share of your home. If you're paying $2,000/month rent and she occupies 1/3 of the space, that's $8,000/year in housing support you're providing. 3. **Medical expenses**: The $3,200 in uncovered medical costs you mentioned definitely counts as support you provided. Keep all those receipts! 4. **Timing matters**: Since you mentioned needing the refund for your HVAC replacement, file early. Dependency claims with disability income sometimes get flagged for additional review, which can delay processing. Given her SSI amount ($10,968) is well above the income limit if it weren't tax-exempt, definitely double-check your tax software handles this correctly. Many people miss out on legitimate dependent claims because their software doesn't properly exclude SSI from the income test.

Based on your situation, you should definitely be able to claim your sister as a dependent! Here's my breakdown: **Income Test**: ✅ PASSED - SSI is tax-exempt, so her $10,968 SSI doesn't count toward the $4,700 gross income limit for 2023. **Support Test**: ✅ LIKELY PASSED - You're covering 73% of household expenses plus her medical costs. Here's how to calculate this properly: - Her total support = SSI payments ($10,968) + your contributions (housing, food, medical, etc.) - You need to provide >50% of this total - Include fair rental value of her living space (major component often overlooked) **Relationship Test**: ✅ PASSED - Sister qualifies as a relative **Residence Test**: ✅ PASSED - She's lived with you all year **Pro tip**: When you file, make sure your tax software correctly excludes her SSI from gross income. Some programs struggle with this and will incorrectly flag her as having too much income. **Documentation to keep**: Receipts for medical expenses, utility bills, grocery receipts, proof of housing costs, and anything showing you provided her support. The IRS may request verification. Given your HVAC situation, file early since dependency claims with disability income sometimes get additional review. You should be able to claim both the dependent exemption and potentially qualify for Head of Household status if you meet those requirements too.

Someone mentioned PFIC earlier and that's actually super important. If your foreign ETFs are considered PFICs (most are), you might need to file Form 8621 for each one, even if they're held in a US brokerage!!! That's separate from the 8938 question.

Thank you all for this incredibly helpful discussion! As someone who's been dealing with similar confusion, I wanted to add a few clarifications that might help others: 1. **Form 8938 vs FBAR**: Both commenters above are correct - since your Chase account is with a US institution, you don't need either form, regardless of what foreign investments are inside it. 2. **PFIC trap**: @Yara Assad and @Olivia Clark are absolutely right about this being a separate issue. Many foreign ETFs are indeed PFICs, and Form 8621 requirements apply regardless of where the account is held. This is often overlooked and can result in significant penalties. 3. **Common mistake**: I see people get confused because they think "foreign investment" = "foreign account" but the IRS distinguishes between the location of the financial institution vs. the underlying investments. @Tyrone Johnson - for your specific situation, I'd recommend asking your accountant to specifically verify whether any of those foreign ETFs qualify as PFICs. The portfolio manager at Chase should be able to provide you with a list of all foreign funds purchased during the year so you can check each one. The tax software and IRS callback services mentioned above sound like great resources for getting definitive answers on these complex international tax situations.

Just wanted to add a few key points that might help clarify things for you: 1. **Holding Period**: Since your uncle gifted these to you "a few years back," make sure you can establish that you held them for more than one year. The long-term capital gains treatment (with the 28% collectibles rate) only applies if the total holding period (including your uncle's ownership time) exceeds one year. 2. **Form 8949 Reporting**: You'll need to report each coin sale separately on Form 8949, then summarize on Schedule D. Don't forget to check Box B for collectibles held more than one year. 3. **Gift Tax Considerations**: Since you mentioned gift taxation in your title - the good news is that as the recipient, you don't owe any gift tax. That would have been your uncle's responsibility if the total value exceeded the annual exclusion limit when he gave them to you. 4. **Dealer Reporting**: If you sold through a coin dealer, they may send you a 1099-B form, but it might not show your correct basis. You'll need to adjust this on your return using the stepped-up basis from the original gift. The $180 per coin gain calculation mentioned earlier looks correct based on your numbers. Just make sure you have some documentation of the original purchase price - even an email from your uncle confirming what he paid would be helpful to keep with your records.

I went through a similar situation with some gold coins my grandmother gave me before she passed away. One thing that really helped me was keeping a detailed spreadsheet with all the information - date of gift, estimated original purchase date and price, date of sale, sale price, and any fees involved. Since you mentioned your uncle told you the approximate original price ($2,315), I'd suggest reaching out to him to see if he has any documentation like receipts, bank statements, or even just an email confirmation from when he purchased them. Even if he doesn't have the exact paperwork, having him write a simple statement confirming the purchase details can be valuable documentation for your records. Also, double-check with whoever you sold the coins to - some dealers keep records of what they've purchased and might be able to provide you with a detailed receipt showing the exact specifications of the coins (year, condition, etc.) which can help support your tax filing. The collectibles tax treatment can definitely feel overwhelming at first, but you're asking all the right questions and it sounds like you have the key information you need to report this correctly!

My husband and I were confused about this last year! One thing that helped us was opening separate accounts and each writing our own checks to our daughter rather than giving from our joint account. Our tax software flagged that we didn't need to file Form 709 this way since each gift was individually under the limit.

Great question! Just to add some clarity to the excellent answers already provided - the key thing to remember is that gift splitting is an election you make, not something that happens automatically just because you're married filing jointly. If your parents want to give your brother more than $18,000 each in 2025 (so more than $36,000 total), they have a few options: 1) Each parent can give up to $18,000 from their own funds without any paperwork, 2) They can give more and elect gift splitting on Form 709 (no tax owed, just reporting), or 3) They can give even larger amounts using their lifetime exemption. One practical tip: if they're planning a substantial gift for the down payment, they might want to consider timing it across tax years. For example, they could give $36,000 in late 2024 and another $36,000 in early 2025, effectively doubling the amount without triggering any gift tax consequences or filing requirements. Also worth noting that the recipient (your brother) never owes taxes on gifts received, regardless of the amount - that's always the giver's responsibility.