Has anyone actually tried deducting it without having a specific medical condition? I'm 37 and just not ready for kids yet but worried about my clock ticking. I don't have cancer or PCOS or anything - just normal age-related concerns.

This thread has been incredibly helpful! I'm 34 and have been putting off this decision partly due to cost. Based on what everyone's shared, it sounds like the key is getting proper medical documentation that frames egg freezing as preservation of reproductive function rather than just "not being ready." A few follow-up questions for those who've been through this: 1. Did your insurance cover any portion that you then couldn't deduct (since you can't double-dip)? 2. How detailed did your doctor's letter need to be - just a paragraph or multiple pages? 3. For those who itemized, what other medical expenses helped you reach that 7.5% AGI threshold? I'm definitely going to discuss this with my fertility clinic and see what documentation they can provide. The potential tax savings could make this much more feasible for me financially.

Has anyone ever had an IRS examination that focused specifically on QSST basis calculations? I'm worried about how much documentation I need to maintain for this type of situation. Been keeping spreadsheets year by year but wonder if that's sufficient.

I've been following this discussion and wanted to share some additional guidance on the documentation piece that @Mateo Gonzalez brought up. Beyond the annual basis worksheets, I'd recommend maintaining: 1. Copies of all S corp K-1s issued during the QSST period 2. Bank statements showing actual distribution flows (whether to trust or beneficiary) 3. Any correspondence with the S corp regarding distribution timing/amounts 4. Documentation of the original QSST election filing One thing I haven't seen mentioned yet is the potential Section 1374 built-in gains tax implications if this was a C corp that converted to S status. While this typically doesn't apply to QSSTs, it's worth checking the S corp's recognition period status. Also, for the related party analysis, don't forget to consider the constructive ownership rules under Section 267(c). The attribution between the trust, trustee, and beneficiary can get complex, especially when family members are involved as both trustees and buyers. The consensus here about adjusting the trust's basis for all pass-through items is absolutely correct, but make sure you're also considering any Section 754 elections if the S corp has partnership interests or other pass-through entities.

Don't forget about the books and supplies portion of qualified expenses! This is a common oversight that could be affecting your calculations. The American Opportunity Credit allows you to count required books, supplies and equipment as qualified expenses, even if you didn't pay for them directly to the school. So if your son purchased textbooks, a required laptop, or other course materials, those costs can be added to the qualified expenses total, which might reduce the taxable portion of the scholarships. Make sure you have receipts for these purchases though. This could potentially reduce his taxable income and increase your available credit.

Quick tip from someone who messed this up last year - if your son received any loans in addition to scholarships, those don't count as taxable income! Make sure you're only counting actual grants and scholarships in your calculations, not the total financial aid package. I made this mistake and incorrectly reported my daughter's entire financial aid package (including loans) as taxable income, which resulted in us overpaying taxes. Had to file an amended return to fix it.

Can someone explain WHY banks give 1042-S for promotions? I got $200 from Bank of America for opening an account and now im dealing with this form too. I'm Canadian also. Isn't a promotion more like a gift than interest??

I'm in a very similar situation as a Canadian who received a US bank promotion bonus! After reading through all these responses, I wanted to share what I learned from my own research and talking to a cross-border tax specialist. For non-resident aliens like us, the key points are: - The 1042-S is just an information return - you don't file it yourself - Income code 29 with zeros in boxes 7 and 10 typically means no US filing requirement - However, you MUST report this income on your Canadian tax return as foreign income One thing I didn't see mentioned is that some provinces have different rules for reporting foreign income, so it's worth checking your specific provincial requirements too. Also, keep the 1042-S form for your records - CRA might ask for it if they have questions about the foreign income you reported. The US-Canada tax treaty generally protects Canadian residents from double taxation on this type of income, which is why you likely see zero withholding. But Canada still wants to tax you on it since you're a Canadian resident.

Has anyone here actually used priortax.com specifically? I'm in a similar situation with unfiled 2016 taxes and wondering if it's worth trying.

Just want to add a reality check here - while you're right to file that 2015 return, don't panic too much about the IRS "coming looking for you." If you were due a refund that year, there are literally no penalties for filing late (you just lose the refund after 3 years, which has already happened). If you owed money, yes there will be penalties and interest, but the IRS is usually pretty reasonable about setting up payment plans. The failure-to-file penalty stops accumulating once you actually file, so getting that return in is definitely the right move. For what it's worth, I've used both professional tax preparers and DIY methods for old returns. If your 2015 situation was relatively simple (just W-2s, maybe some basic deductions), the manual route with IRS forms might be cheaper than you think. But if you had complicated stuff going on during that divorce year, spending the money on professional help could save you headaches and potentially money in the long run.