Just to add a data point here - I had this exact situation last year. LLC with S-corp election, filed 1120-S about 75 days late. I can confirm 100% that the IRC-6699 S-corporation penalties applied, not the LLC penalties. I tried to argue with the IRS that since my business is "technically" an LLC, the LLC penalty structure should apply (which would have been less in my case). They shut that down immediately. Once you elect S-corp taxation, you're treated as an S-corp for ALL tax purposes, including penalties. The good news is I was able to get a partial abatement based on reasonable cause (I had documentation showing my accountant had a family emergency). They reduced my penalty by about 40%.

One thing nobody has mentioned yet - there's a difference between late FILING penalties (Form 1120-S) and late PAYMENT penalties. If you've been making your estimated tax payments as shareholders, you might only be dealing with the late filing penalty. The IRC-6699 penalty ($220 per shareholder per month) applies to late FILING of the 1120-S. But if you also have unpaid taxes at the shareholder level (on your 1040s), that's a separate penalty structure. Just something to keep in mind when calculating what you might owe.

Has anyone else had issues with farm startup costs? I'm in a similar situation (40 acre property, making money from online content but not actual farm products yet), and my tax software keeps flagging my equipment purchases saying I need to depreciate instead of taking Section 179. So confused about what's allowed in the first year.

This is a really interesting situation that's becoming more common! I'm dealing with something similar - I have a small organic vegetable operation that I'm documenting on TikTok and Instagram, and the social media income is actually outpacing my produce sales right now. From what I've researched and discussed with my accountant, keeping them separate (Schedule C for content, Schedule F for farm) seems to be the safest approach. The IRS likes clear distinctions between different types of business activities. Even though your YouTube content is about the farm, the income source is fundamentally different - you're being paid by Google for ad revenue, not by customers for farm products. One thing I'd add is to make sure you're tracking any equipment or expenses that serve both businesses. For example, if you buy a tractor that you use 80% for actual farming and 20% for filming content, you'll need to allocate those costs appropriately between the two schedules. Same goes for things like your phone if you're using it to film and manage both businesses. Also, don't worry too much about the farm showing losses initially - that's completely normal for startup agricultural operations. Just make sure you have a solid business plan showing how you intend to generate farm income in the future. The fact that you're actively working the land and making investments shows business intent rather than hobby activity.

Everyone keeps mentioning accountants, but I think you need a tax attorney for a situation this complex. I made the mistake of just using my regular CPA when I hadn't filed for 5 years, and we ended up with the IRS rejecting the voluntary disclosure and hitting me with serious penalties. An attorney can give you protection through attorney-client privilege that a CPA can't. Just my 2 cents after learning the hard way.

I was in a very similar situation - didn't file for 4 years with my consulting LLC. The key thing that helped me was getting organized BEFORE meeting with a tax professional. I spent weeks trying to reconstruct my financial records from old bank statements and whatever receipts I could find. One practical tip: if you used business credit cards or had dedicated business bank accounts, those statements will be your lifeline for reconstructing deductible expenses. Even without receipts, you can often identify legitimate business expenses from the merchant names and dates. Also, don't panic about the penalties. Yes, there will be some, but the IRS has programs like "first-time penalty abatement" that can help reduce them if you have a clean record otherwise. The fact that you're proactively addressing this before they contact you works heavily in your favor. For your income jump to $650k this year - make sure you're making quarterly estimated payments NOW if you haven't already. That's probably more important than the back years at this point since the current year liability will be substantial. Start gathering your records immediately and find a tax pro who specializes in unfiled returns. Don't let this drag on any longer - every month you wait adds more penalties and interest.

Question - do I still need to pay into US Social Security if I'm paying into NZ's superannuation system? Feels like I'm double paying for retirement!

As someone who just went through this exact situation last year after moving to Auckland, I can definitely relate to the overwhelm! The key thing that helped me was getting organized early and understanding that yes, you absolutely still need to file US taxes. Since you worked in both countries during 2023, you'll need to gather documents from both employers - your final W-2 from the Boston company and whatever tax documents your NZ employer provides (they should give you an IR3 or similar). One thing I wish I'd known earlier: keep detailed records of your exact dates of travel and residence. The IRS is very specific about qualifying days for the Foreign Earned Income Exclusion, and having precise documentation makes everything smoother. Also, don't stress too much about the NZ tax year difference (April to March vs January to December). You'll report your 2023 calendar year income to the US, regardless of how NZ splits it across their tax years. The good news is that once you get through your first year of expat taxes, subsequent years become much more routine. You've got this!

Has anyone used TurboTax to file with Form 8233 and treaty benefits? I'm about to file for last year and I had treaty benefits from an internship, but I'm not sure if the basic TurboTax can handle this or if I need some premium version.

Great point about using the right tax software! I made this mistake my first year and it was a nightmare to fix. Lucy is absolutely right - TurboTax will mess up your tax situation as a nonresident alien. I used Sprintax last year and it handled my Form 8233 treaty benefits perfectly. It walks you through all the nonresident alien forms (1040NR, 8843, etc.) and has specific sections for treaty benefits from different countries. Most universities have discount codes or sometimes even free access to Sprintax - check with your international student office first. Also, keep in mind that if you used Form 8233 during the year, you'll need to report those treaty benefits on your tax return even though taxes weren't withheld on that income. The software should guide you through this, but it's important to be consistent between what you claimed on Form 8233 and what you report on your 1040NR.