Slight tangent but might be useful - watch out for the "substantially equal periodic payments" rule getting confused with the rollover rule. My advisor messed this up for me. I thought I could take out regular payments from my IRA without penalty using the 72(t) SEPP program AND do a 60-day rollover in the same year. Turns out doing a rollover terminates your SEPP plan and triggers penalties on ALL previous distributions. Cost me thousands in surprise taxes. Just mentioning this because sometimes when people are looking at ways to access retirement funds early, these different rules get mixed up.

Great question about Roth IRA rollovers! I've been through something similar and learned the hard way about the complexity of these rules. One important detail I haven't seen fully addressed - when you withdraw from a Roth IRA, the IRS considers withdrawals to come from contributions first (FIFO - first in, first out). So if you've contributed $20,000 over the years and your account is worth $25,000, your first $20,000 withdrawn would be considered contributions and wouldn't face the 10% penalty regardless of the rollover. However, once you hit the earnings portion (that $5,000 in my example), those ARE subject to the 10% penalty if you're under 59½ - unless you complete a valid 60-day rollover or qualify for an exception. The tricky part with your dual withdrawal scenario is that even if both withdrawals combined stay within your contribution basis, you still can only do ONE rollover per 12-month period. So if something goes wrong and you can't complete the rollover for any reason, you'd want to make sure your total withdrawal amount doesn't exceed your contribution basis to avoid penalties on earnings. I'd strongly recommend getting documentation from your IRA custodian showing exactly how much you've contributed versus earned before making any withdrawals. This gives you a clear picture of your penalty-free withdrawal capacity.

The most important thing here is to just file ASAP! I put off filing late once and it only made the penalties worse. Even if you can't pay what you owe right now, file the return anyway and then set up a payment plan.

Just want to add some reassurance here - I was in the exact same situation two years ago and it really wasn't as bad as I thought it would be. Filed about 3 weeks late using TurboTax (similar to FreeTaxUSA) and the whole process was identical to filing on time. The key things that helped me: 1) File for tax year 2023 (not 2024), 2) E-filing still works normally even after the deadline, and 3) If you're getting a refund, you won't face penalties - just a delayed refund. I ended up owing about $200 and the penalty was only around $15 total. Way less scary than I'd built it up in my head! The IRS even sent me a clear breakdown of exactly what the penalty was for. Don't beat yourself up about it - life happens and this is more common than you think. Just get it filed in the next few days and you'll be fine!

Has anyone used H&R Block's expat tax service? I'm in a similar situation (US citizen in Auckland) and wondering if they're any good for international situations. Their regular service messed up my taxes before I left the States so I'm hesitant, but they advertise an expat specialty service.

I went through this exact same situation last year! The key thing to remember is that the US tax year mismatch with NZ isn't as complicated as it seems - you just report your NZ income earned during the US tax year (Jan-Dec 2023) on your US return. A couple of practical tips from my experience: 1. Keep detailed records of your income from both countries with dates - this makes everything easier 2. The Foreign Tax Credit can be really valuable, but you'll want to calculate whether that or the Foreign Earned Income Exclusion gives you better tax savings 3. Don't forget about potentially reporting any NZ bank accounts on your FBAR if the total exceeds $10,000 at any point during the year One thing I wish I'd known earlier - make sure you understand NZ's tax residency rules too. Since you qualify as a tax resident there, you'll need to report your US income on your NZ return as well. The timing can get tricky since you might file your US return in April but your NZ return isn't due until July. If you're comfortable with TurboTax, their Premier version handles foreign income reporting pretty well. Just make sure you have all your NZ pay slips converted to USD using the proper exchange rates for when you earned the income.

OP, I'm a little concerned about the $78k valuation on a 45-acre conservation easement - that seems potentially low depending on your location and development potential. Make sure your appraiser specifically valued the development rights you're giving up, not just the current agricultural or timber value. The proper valuation should be the difference between the property's value before the easement and after the easement.

Thanks everyone for all the helpful advice! I had no idea conservation easements were so complex from a tax perspective. Based on what you've all shared, I'm definitely going to file an amended return, but I want to make sure I do it right the first time. A few follow-up questions: The appraisal was done by someone the land trust recommended who said he had experience with conservation properties, but now I'm wondering if I should get a second opinion given the concerns about valuation. The property is in a rural area about 30 minutes from a growing suburb, so there could be development potential I'm not fully aware of. Also, should I work with a tax attorney first before filing the amendment, or can I start with the amended return process and only involve an attorney if issues come up? I want to be thorough but also don't want to overcomplicate things if my situation is straightforward. The land has been in our family since the 1940s and we genuinely want to protect it - this wasn't done as any kind of tax shelter scheme. Just want to make sure I handle the tax side properly while there's still time to amend.

am i the only 1 who thinks its crazy we gotta jump thru all these hoops just to get OUR money back??? 🤡 system is broken af

I've been dealing with this exact same issue! What finally worked for me was calling the practitioner priority line at 1-866-860-4259 instead of the main number. Even though it's technically for tax professionals, they sometimes transfer you to the right department and the wait times are way shorter. Also, if you press 2-1-3-2 in the phone menu, it usually gets you to a human faster than going through the automated system. Don't give up - I know it's frustrating but you'll get through eventually!