I've been following this thread with great interest as I'm currently dealing with a similar nightmare scenario. The IRS rejected my 2021 1120-S claiming they have no record of my Form 2553, despite having filed it properly and operating as an S-corp for years. What really caught my attention in this discussion is the combination of approaches mentioned - the systematic documentation requests (Business Master File Account Transcript, Form 4506-T) paired with the newer tools like taxr.ai for analysis and Claimyr for actually getting through to the right IRS department. I'm particularly intrigued by Hattie's point about requesting the complete account transcript. In my case, the IRS has been processing my quarterly employment tax returns as an S-corp for three years, but suddenly claims they have no record of the election for my annual return. This system inconsistency seems to be exactly what these transcripts would reveal. For dissolved entities like yours, I'd also suggest checking if your state has any pending tax issues that might be creating federal complications. In some cases, state-level entity problems can cause the IRS to question or override federal elections. The timeline pressure you're under makes this even more critical. Based on what I've read here, I'd probably pursue multiple approaches simultaneously - file for the transcripts and protective claim while using one of the callback services to get through to the Business Entity department directly. The worst thing would be to let deadlines pass while waiting for one approach to work.

I've been dealing with IRS entity classification issues for years as a tax professional, and this thread has some excellent advice. I want to emphasize a few critical points for your situation: First, the fact that your original 1120-S was accepted is huge evidence in your favor. The IRS has internal controls that should have rejected it immediately if there was truly no S-corp election on file. This acceptance creates what we call "administrative estoppel" - they can't now claim they never recognized your status when they previously processed returns based on that status. Second, since your company is dissolved, you're working against some strict deadlines. The IRS generally allows 3 years and 75 days from the original due date to correct entity elections, but dissolution can complicate this. I'd strongly recommend filing Form 9100 (Application for Extension of Time) immediately while you gather your documentation. This preserves your rights to retroactive relief even if the standard deadlines have passed. Third, beyond the excellent suggestions about transcripts and callback services, consider requesting a copy of your complete IRS file using the Freedom of Information Act (FOIA). Sometimes documents exist in the system but aren't showing up in standard searches. A FOIA request forces them to do a comprehensive search. The combination approach mentioned by others is spot-on - use the systematic documentation requests to build your case while using callback services to get to the right people who can actually resolve it. Time is your enemy here, so parallel processing is essential.

Something to consider - if one of you makes significantly more than the other, you might want to adjust your withholding differently. When my wife and I got married, we found that we needed to withhold extra from the higher-earning spouse to avoid owing at tax time. Also, don't forget about that side job with tips! Tips are taxable income and if they're not withholding enough for those, you could end up with a surprise tax bill. I'd recommend putting a little extra withholding on that job's W-4.

One thing nobody's mentioned - you can always adjust your W-4 throughout the year if you find the withholding isn't right! My husband and I got married last year and had to tweak our withholding twice before we got it right. You might consider starting conservative (slightly higher withholding) and then after a few months, use the IRS Withholding Estimator again to see if you're on track. Many people don't realize you can submit a new W-4 to your employer anytime your situation changes.

The collective wisdom around here is that persistence pays off, but with strategy. The IRS actually publishes their call center metrics, and Mondays and Tuesdays are statistically the worst days to call (who knew tax problems strike on weekends? 😏). Thursdays between 10-11am and 2-3pm Eastern tend to have the lowest volume. One trick that's worked for several folks here: if you have a specific form question, call the forms ordering line (800-829-3676) which usually has humans answering, then politely explain your situation and ask to be transferred to the appropriate department. The forms people are often the unsung heroes of the IRS phone system. Just be patient and unfailingly polite - these folks deal with frustrated people all day.

I've had success with a hybrid approach that combines several strategies mentioned here. First, I use the callback feature on the main line (800-829-1040) - press 2 when they offer callback instead of waiting on hold. This preserves your place in queue while you go about your day. Second, I've found that calling exactly at 12:00 PM ET often works because that's when they return from lunch and queues temporarily clear. For 1099 discrepancies specifically, you might also try the Automated Underreporter (AUR) unit directly if you've received any notices - they have a dedicated line that's less congested than general inquiry. The key is having all your documentation ready before calling: the 1099 in question, your filed return, and any related correspondence. I've noticed agents can resolve these issues much faster when you have everything at hand rather than having to call back multiple times.

Has anyone used TurboTax Self-Employed for this kind of stipend situation? Wondering if it's worth the extra cost compared to the regular version.

Great question, Ravi! I went through something very similar with a research stipend a couple years ago. Here are the key things I learned: 1. **You'll get a 1099-NEC** - The organization will send you (and the IRS) a 1099-NEC form showing the $4,000 as non-employee compensation. 2. **Self-employment tax applies** - You'll owe the full 15.3% self-employment tax (normally split between employer/employee), plus regular income tax on top of that. 3. **Quarterly payments** - With $4,000, you'll likely owe around $600-800 in self-employment tax alone, plus income tax depending on your bracket. Since this could easily put you over the $1,000 threshold, I'd recommend making quarterly estimated payments to avoid penalties. 4. **Track expenses** - Keep receipts for anything directly related to your internship - supplies, travel, home office space if you work remotely, etc. These can reduce your taxable income. 5. **File Schedule C** - You'll report this income and any deductions on Schedule C (Profit or Loss from Business) with your regular tax return. My advice: Set aside 30% of each stipend payment immediately. Better to have too much saved than scramble to pay a big tax bill later! The IRS doesn't mess around with self-employment tax. Good luck with the internship!

I'm in my 3rd year as an agent and I don't even bother with the clothing deductions anymore. Focus on the big stuff instead: - Mileage (huge deduction, track EVERY showing) - Home office (if you have dedicated space) - Marketing (social media ads, flyers, photography) - Continuing education - E&O insurance - Desk fees - Technology (portion of phone, laptop, internet) These add up to WAY more than dry cleaning ever would, and they're all clearly allowed. Why risk an audit over dry cleaning when there are so many legitimate deductions available?

Great thread everyone! As someone who's been in real estate for about 5 years now, I can confirm what others have said - skip the dry cleaning deduction and focus on the big ones that actually matter. I learned this the hard way my first year when I spent hours trying to justify clothing expenses, only to have my CPA tell me it wasn't worth the risk. Now I focus on tracking: - Every single mile driven for business (this alone saved me about $4,000 last year) - All my marketing expenses including professional photos for listings - My MLS fees, lockbox fees, and board dues - Portion of my cell phone and internet since I use them for business - Business meals with clients (50% deductible) The mileage tracking especially adds up fast when you're showing properties all over town. I use an app that automatically tracks my trips and I just mark which ones were business-related at the end of each day. Don't get hung up on the small stuff like dry cleaning - there are so many legitimate deductions available to real estate agents that you'll easily make up for it with the safer options.