Has anyone mentioned the "reasonable compensation" requirement for S-Corps? This is where most expats get tripped up. The IRS requires you to pay yourself a "reasonable salary" subject to FICA taxes before taking distributions. With FEIE, this gets messy because only the salary portion qualifies for FEIE (up to the limit), not the distributions. So you might save on self-employment tax but lose FEIE benefits on the distribution portion.

I went through almost the exact same situation last year - LLC with FEIE benefits, considering S-Corp election, and dealing with unresponsive tax professionals. Here's what I learned that might help: The electronic signature issue will likely save you, as others mentioned. The IRS is incredibly strict about wet signatures on Form 2553. But definitely call proactively rather than waiting - it shows good faith and creates a paper trail. Regarding the S-Corp vs FEIE analysis, here's the key issue most people miss: with S-Corp status, you're required to pay yourself "reasonable compensation" as an employee before taking distributions. Only that salary portion qualifies for FEIE, not the distributions. So if your business income is $100k and you set reasonable salary at $60k, only the $60k qualifies for FEIE. The remaining $40k in distributions doesn't qualify for FEIE but also isn't subject to SE tax. Compare this to LLC status where your entire $100k of business income qualifies for FEIE (up to the annual limit) but is subject to SE tax. The math really depends on your specific income levels and how much of your income falls under the FEIE limit. In many expat situations, especially with income under $120k, staying as an LLC with full FEIE benefits actually comes out ahead. Get a proper analysis done before making any decisions - this isn't something to guess on.

Pro tip: set up informed delivery with USPS so you know exactly when that check hits your mailbox

I went through this exact same situation last year. The 2-4 week timeline is pretty accurate, but here's what helped me: I called the IRS customer service line (1-800-829-1040) about 10 days after my deposit was rejected and they were able to confirm that my paper check had been processed and give me a rough mailing date. Also double-check that your address on file with the IRS matches exactly what you have with USPS - even small differences can cause delays. Hang in there, the check will come!

I'm dealing with a very similar situation right now with my late father's estate. One thing I learned that might help - even though your mom's assets were distributed through beneficiary designations, the IRS can still pursue what's called "transferee liability" against the beneficiaries if there were unpaid taxes at the time of transfer. The key is getting proper authorization to deal with the IRS on her behalf. Form 56 is definitely the right path, but make sure you're sending it to the correct IRS processing center for your state. I made the mistake of sending it to the wrong location initially and it delayed everything by months. Also, document everything with the IRS phone calls - dates, times, agent names/ID numbers. The inconsistent information you're getting is unfortunately typical, but having records helps if you need to escalate later. You might also want to request a manager or supervisor when you call back, as they tend to be more knowledgeable about deceased taxpayer procedures. The $12,300 won't just disappear, but you do have options for penalty abatement and possibly even an offer in compromise if the total distributed assets were less than the tax debt. Don't let the interest and penalties keep accumulating while you're stuck in this bureaucratic maze.

I went through this exact nightmare when my grandmother passed in 2022. The IRS bureaucracy around deceased taxpayers is absolutely maddening, but here's what finally worked: First, you're right that the tax liability doesn't just disappear. Since your mom's assets were distributed through beneficiary designations, you and your siblings could potentially be liable as transferees if the IRS can prove the tax debt existed when you received the assets (which it sounds like it did). The Form 56 route is correct, but here's the key - you need to establish yourself as the "informal fiduciary" since no formal estate was opened. Include a cover letter explaining that all assets were distributed via beneficiary designations and that you're acting on behalf of the deceased taxpayer to resolve outstanding tax matters. Also, when you call the IRS, specifically ask for the "Deceased Taxpayer" unit - don't let them transfer you to general collections. The regular agents literally don't have training on these situations, which explains the ridiculous advice about getting a power of attorney from a dead person. Once you get Form 56 processed, you can request penalty abatement for reasonable cause (accountant error) and potentially set up a payment plan if needed. The actual tax plus interest will likely still be due, but you can eliminate the penalties which are usually a big chunk of these bills. Don't ignore this - the IRS has up to 10 years to collect and can absolutely pursue transferee liability against beneficiaries. Better to deal with it now before more penalties and interest accumulate.

question - if I estimate now using FreeTaxUSA 2023 software and create an account, can I just log back in when I have my actual W-2 and 1099 forms and file from there? or would I need to start over?

Thanks for the heads up about the early release! I've been using FreeTaxUSA for the past few years and really appreciate being able to do tax planning before the rush. One tip I'd add - if you're estimating now, make sure to save different scenarios. I usually create versions with conservative estimates and then more optimistic projections to see the range of what I might owe or get back. Also worth noting that if you have any major life changes planned (marriage, new job, etc.), you can model those too to see how they'd impact your taxes. Really helps with financial planning for the year ahead.

Just a heads up - if you end up filing without the official 1099-B, make sure you check the box on Form 8949 that indicates you're reporting transactions that weren't reported to you on a 1099-B. This lets the IRS know you're being transparent about not having the official form. Also, document EVERYTHING. Download your transaction history from Robinhood NOW, before it potentially disappears from your easy access. Take screenshots of your attempts to contact them. If there's ever an audit question, you want to show you made every effort to get the correct documents.

I work in tax preparation and see this Robinhood issue frequently. Here's what you need to know from a professional perspective: 1. **You MUST report all stock sales regardless of receiving a 1099-B.** The IRS requires you to report capital gains/losses even without the form. 2. **Robinhood's delay might be legitimate.** Complex situations like wash sales, corporate actions, or basis adjustments can delay forms until March 15th. 3. **For immediate action:** Download your complete transaction history from Robinhood (Account → Statements → Activity). This will have all your trades with dates, quantities, and prices. 4. **Calculate manually if needed:** Use FIFO (First In, First Out) method unless you specifically elected otherwise. Your proceeds minus your cost basis equals your gain/loss. 5. **Don't forget dividends:** Even $10+ in dividends must be reported. Check if you received a 1099-DIV or if it's combined with other forms. The key is accurate reporting with proper documentation. I've helped clients through IRS correspondence when brokers were late with forms, and as long as you report everything accurately and keep records, you'll be fine. Consider filing an extension if you're uncomfortable proceeding without the official form.