Has anyone calculated whether this actually saves money in the long run? I'm in a similar situation and trying to figure out if the tax benefits outweigh the hassle of the transfer.

This is a complex situation that really requires careful planning. I went through something similar with my S-Corp about 18 months ago and learned some hard lessons. One thing I don't see mentioned yet is the timing of when you do the valuation for the distribution. The IRS requires you to use fair market value on the date of distribution, but with volatile investments, this can make a huge difference. I made the mistake of not coordinating the valuation date with my transfer, and ended up with a mess when my ETFs dropped significantly between when we calculated the distribution value and when Fidelity actually processed the transfer. Also, make sure your S-Corp election is still valid before doing this. I discovered during my transfer that we had inadvertently violated some S-Corp requirements a year earlier (related to shareholder loans), which could have invalidated our election. Fortunately we were able to fix it retroactively, but it could have been a disaster. My advice: get everything documented in writing from your CPA first, including exactly how they plan to handle the mechanics of the transfer, the valuation method, and how it will be reported on both your business and personal returns. Don't rely on verbal assurances for something this significant.

Has anyone ever had the IRS question their home sale reporting? I'm worried because we're in a similar situation where we're not going to owe any taxes due to the exclusion, but we did a ton of improvements over the years and I'm not sure I have receipts for all of them. Some were done 8+ years ago.

Just want to add a practical tip from my experience - even though you can't deduct the loss on your personal residence, make sure you keep detailed records of everything related to the sale. The IRS has been increasingly scrutinizing home sales, especially when large exclusions are claimed. For your situation with the negative $121k after exclusion, you'll report it as zero taxable gain, but having all your documentation organized (purchase records, improvement receipts, selling costs, etc.) is crucial. I'd recommend creating a simple spreadsheet that shows your calculation step by step - purchase price, improvements, selling costs, gross gain, exclusion applied, final taxable amount. Also, double-check that all your improvements qualify for basis adjustment. Generally, repairs don't count but improvements that add value, prolong the home's life, or adapt it to new uses do count. Kitchen remodels and basement finishing definitely qualify, but make sure you're not including regular maintenance items.

This is probably a dumb question but does anyone know how long it typically takes for a mailed return to show up in the "Where's My Refund" tool? I mailed mine 3 weeks ago and it still says "Return Not Received" when I check.

Just wanted to add one more important point about the postmark rule - make sure you're using regular USPS mail or an approved private delivery service like FedEx or UPS. I learned the hard way that some local courier services don't count for the postmark rule because they're not IRS-approved delivery services. Also, if you're mailing multiple forms (like your return plus an extension), make sure they're all postmarked by the deadline. I once sent my extension on time but forgot to include a required payment voucher, and had to send that separately. Even though my extension was valid, I still got hit with penalties because the payment was late. One last tip: if you're really stressed about timing, you can actually hand-deliver your return to certain IRS offices, but they have very limited hours and locations for this. Most Taxpayer Assistance Centers stopped accepting returns during COVID and haven't resumed that service. But it's worth checking if you have one nearby and you're cutting it really close!

I'm dealing with the exact same issue! My spouse and I both work full-time with similar salaries and we've owed taxes for three years straight despite trying to adjust our withholding each time. Reading through these responses, it sounds like the "Married but withhold at higher Single rate" option might be our solution. I had no idea the old allowance system was completely phased out - that explains why all the advice I was finding online seemed outdated. The point about payroll systems calculating withholding per paycheck without knowing about your spouse's income really makes sense. Each employer thinks we're in a lower bracket individually, but combined we're actually higher. I think I'll try the IRS Withholding Estimator first since it's free, and if that doesn't work out, maybe look into some of the other tools mentioned here. Thanks everyone for sharing your experiences - it's reassuring to know we're not the only ones struggling with this!

I went through this exact same frustration for years! What finally worked for me was a combination of strategies mentioned here. First, I switched both my husband and my W-4s to "Married but withhold at higher Single rate" - this immediately got us much closer to the right amount. The key insight that changed everything was understanding that when both spouses earn similar incomes (like you mentioned), you often hit what's called the "marriage penalty." Each employer's payroll system assumes your spouse either doesn't work or earns very little, so they withhold based on tax brackets that are too low for your actual combined income. Here's what I'd recommend as your action plan: 1) Update both W-4s to "Married filing jointly" but check the "higher withholding rate for single or married filing separately" box, 2) Use the IRS Withholding Estimator with your last paystubs to see if you need additional withholding on line 4(c), and 3) Check your first few paystubs after the change to make sure the new withholding amounts look reasonable. It took me three tax seasons of owing money to figure this out, but once I did, we've been getting small refunds ever since. The peace of mind is worth so much more than the extra few dollars withheld each paycheck!

I'm working on this exact same situation for my Romanian SRL and wanted to share some additional insights after going through most of the process. One thing I discovered that might help others: if you're unsure about any section of the SS-4, the IRS actually has a dedicated helpline for international applicants at 267-941-1099. While it's still difficult to get through (definitely recommend that Claimyr service others mentioned), they can provide specific guidance for foreign entity classifications before you submit. Also, for Romanian SRLs specifically, I confirmed with an IRS representative that "C - Corporation" is indeed correct, just like other European limited companies mentioned here. The agent explained that most European limited liability companies fall under this classification because they share the key characteristics: separate legal entity status and limited liability for owners. I'm still waiting on my EIN (submitted 2 weeks ago via the international fax), but everything seems to be processing normally. The address formatting advice from previous comments was spot-on - I used the exact format from my Romanian business registration with "ROMANIA" clearly marked at the end. Thanks to everyone who contributed their experiences here - it made navigating this process much less stressful!

I've been following this thread as someone who recently completed the EIN application process for my Hungarian Kft., and I wanted to add a few observations that might help future applicants. First, the C-Corporation designation advice here is absolutely correct - I can confirm this worked perfectly for my Hungarian limited company. The IRS processed it without any questions or delays. One thing I'd add that I haven't seen mentioned: if you're applying during peak tax season (January-April), expect longer processing times. I submitted my SS-4 in March and it took nearly 4 weeks instead of the typical 2-3 weeks others have reported. The IRS international line confirmed this was due to higher application volumes during tax season. Also, regarding the international fax number (+1-304-707-9471), I recommend calling your fax service provider first to confirm they can send to US numbers. Some European fax services have restrictions on international transmissions that I discovered the hard way after my first attempt failed. For anyone still on the fence about those callback services mentioned earlier - I was initially skeptical but ended up using Claimyr when I needed to check my application status. It genuinely worked as described and saved me hours of frustration trying to get through on my own. The key takeaway is that this process is very manageable once you know the right steps. European limited companies should confidently select C-Corporation, use "Banking purpose" if that's your intent, and be patient with processing times. This community's collective experience makes it much easier for newcomers to navigate successfully.