I'm going through this exact same situation right now! Filed my 2021 taxes about 6 months late due to a job loss and subsequent move, and I'm staring at about $580 in penalties that I've already paid off. This entire thread has been like finding gold - so much practical advice that you just can't get from reading the IRS instructions alone. The systematic approach everyone has developed here makes so much sense: get the account transcript for specific penalty codes, use both FTA and reasonable cause as backup options, create a detailed timeline with supporting docs, and do the dual fax/certified mail submission. I had no idea about tools like the IRS where-to-file lookup or that transcript phone number (1-800-908-9946). What really stands out to me is how organized and thorough everyone who got approved was in their submissions. It's clear that making the IRS reviewer's job easier by providing everything they need in a logical format makes a huge difference in both approval chances and processing time. I'm feeling much more confident about tackling this now. My job loss situation led to a cross-country move for new employment, so I have documentation showing the timeline of events and why I couldn't handle tax filing during that period. Plus I have a clean filing history for the past 6 years, which several people mentioned helps with the case. Thanks to everyone who shared their experiences and specific tips. This community approach to helping each other navigate these stressful IRS situations is exactly what people need when they're feeling overwhelmed by the process!

This thread has been absolutely invaluable! I'm dealing with a very similar situation - filed my 2022 taxes about 4 months late due to a divorce and relocation, and ended up with around $420 in penalties that I've already paid. Reading through everyone's detailed experiences and seeing the actual success stories has completely changed my approach. I was initially just going to write a brief explanation and hope for the best, but it's clear that being systematic and thorough is what gets results. My plan based on all the excellent advice here: 1. Call 1-800-908-9946 to get my account transcript with specific penalty codes 2. Use the IRS where-to-file tool to get the exact mailing address for my state 3. Structure my request with both FTA and reasonable cause as alternative grounds 4. Create a detailed timeline showing how the divorce proceedings and custody issues prevented timely filing 5. Include my 7+ year clean filing history as supporting evidence 6. Use the dual fax/certified mail strategy for optimal processing I have court documents, attorney correspondence, and moving records that clearly establish the timeline of events. The "but for" test mentioned by Miguel's tax preparer really helped me understand how to frame the causal relationship between my circumstances and the late filing. One question for those who've been through this - did anyone include information about estimated processing times in their cover letter, or is it better to just focus on the facts of your case? I'm trying to balance being thorough without making the submission unnecessarily long. Thank you all for sharing such practical, detailed guidance. This community support makes navigating IRS procedures so much less intimidating!

I've been following this thread with great interest since I'm dealing with a very similar situation. My single-member LLC had unexpected growth in 2022, and like you, I got hit with a substantial tax bill that could have been significantly reduced with S-Corp treatment. Based on everything I've researched and the excellent advice shared here, the key points seem to be: 1) This IS possible under Revenue Procedure 2013-30, but it's not as simple as just filing an amended return 2) You need BOTH Form 8832 (entity classification election) AND Form 2553 (S election) 3) The "reasonable cause" statement is absolutely critical - document everything showing you intended to minimize taxes legally 4) Timeline matters - you generally have 3 years from filing date or 2 years from payment date to amend I'm curious though - for those who've successfully gone through this process, how did you handle the self-employment tax aspect? One of the biggest advantages of S-Corp status is avoiding SE tax on distributions, but I'm wondering if the IRS scrutinizes reasonable salary amounts more closely when you're making a retroactive election. Also, did anyone run into issues with state tax authorities? My state (California) has its own S-Corp election requirements, and I'm not sure if they automatically follow the federal late election or if I need to file separate state forms. Thanks to everyone who's shared their experiences - this thread has been incredibly valuable!

I've been through a similar situation and want to add a few practical considerations that might help with your decision-making process. While the technical aspects have been well covered here (Rev. Proc. 2013-30, Forms 8832 and 2553, reasonable cause statements), there are some financial realities to consider before diving in: 1) **Professional fees can add up quickly** - Between CPA fees for the complex filings, potential attorney consultation, and ongoing S-Corp compliance costs (payroll processing, additional tax returns), you could easily spend $5,000-$10,000 in the first year alone. Make sure your potential tax savings justify these costs. 2) **Payroll complexity** - If your retroactive election is approved, you'll need to establish reasonable compensation for 2022 and handle the payroll tax implications. This often means setting up payroll systems retroactively and potentially owing additional employment taxes that weren't previously required as an LLC. 3) **State compliance varies wildly** - Some states make this process relatively straightforward, while others (looking at you, California and New York) have their own complex requirements that don't always align with federal elections. 4) **Documentation timeline** - Start gathering your supporting documentation now. Business bank statements showing consistent profitability, any communications about business growth or tax planning, and records of when you first learned about S-Corp benefits will all strengthen your reasonable cause argument. The tax savings can definitely be worth it (I saved about $22k over two years), but go in with realistic expectations about the complexity and costs involved. It's not a magic bullet, but it can be a valuable strategy if executed properly.

This is exactly the kind of HSA confusion that trips up so many people! Your W-2 is actually correct - Box 12 Code W should show the combined total of both your contributions ($1,950) and your employer's contributions ($975), which equals $2,925. The key thing to remember is that your payroll deductions for HSA are pre-tax contributions, so they get lumped together with employer contributions in Box 12W. This is different from retirement plans where employee and employer contributions might be reported separately. Since your total is $2,925 and well under the 2024 limit of $4,150 for individual coverage (or $3,650 if this was for 2023), you're in good shape. No red flags here - your employer reported everything correctly!

I had this exact same confusion last year! Your W-2 is correct - Box 12 Code W should include both your employee contributions AND your employer's contributions. The $2,925 total you're seeing is exactly right ($1,950 from your payroll deductions + $975 employer match). What helped me understand this is that when you make HSA contributions through payroll deduction, they're taken out pre-tax, which means they're treated similarly to employer contributions for reporting purposes. That's why they get combined in Box 12W rather than reported separately. The good news is you're well under the contribution limits, so no worries about red flags with the IRS. For 2024, the limit is $4,150 for individual coverage, so you have plenty of room if you wanted to contribute more. Just make sure to keep good records of your contributions throughout the year to avoid any confusion next tax season!

Don't forget to check what your 401k money is actually invested in! I was contributing to get my employer match for years before I realized my money was sitting in a default money market fund making almost nothing. When you increase your contribution, make sure you're invested in something appropriate for your age. At 29, you probably want to be mostly in stock funds for long-term growth. Most 401k plans have target date funds that automatically adjust your investments as you get closer to retirement age.

Great question! You're already doing the smart thing by getting that full 5% match - that's literally free money. At 29, you have time on your side which is huge for compound growth. Given your situation, I'd suggest gradually increasing your 401k contribution to around 10-12% of your salary if you can swing it. With a $62k income, that extra 5-7% would be about $3,100-$4,340 more per year, but remember it reduces your taxable income so your take-home won't drop by the full amount. The key is finding balance - your 4.2% student loan rate isn't terrible, so it's not an emergency to pay it off early. I'd prioritize the 401k increase first since you're in the 22% tax bracket and getting that deduction now makes sense. Plus, starting a Roth IRA for your house fund (as others mentioned) gives you flexibility since you can access contributions penalty-free. Don't try to do everything at once though. Maybe bump your 401k to 8% first, see how it feels budget-wise, then consider adding a small Roth IRA contribution later. The most important thing is consistency - even small increases in your contributions now will make a massive difference over the next 35+ years until retirement.

Just to clarify something important - if your earnings from this company were over $600 for the year, they are actually REQUIRED by law to send you a 1099. You might want to follow up with them more firmly or contact the IRS to report them, especially if this is affecting multiple contractors as they indicated. You can still file your taxes correctly without the form as others have mentioned, but the company is definitely not following proper tax procedure here. "Issues with their bank" is not a valid excuse for failing to meet tax documentation requirements.

I've been through this exact situation and wanted to share what worked for me. When a company failed to provide my 1099 despite earning over $2,000 from them, I took a two-pronged approach. First, I filed my taxes accurately using my own records just like everyone here has mentioned - reported all income on Schedule C through my tax software (I used H&R Block but the process is the same). The key is being meticulous with your documentation. Second, I filed Form SS-8 with the IRS to get a determination on my worker status, since companies sometimes claim "contractor" to avoid proper tax reporting. Turns out I should have been classified as an employee, which explained why they were dodging the 1099 requirement. Even if your classification was correct, you can still file Form 3949-A to report tax law violations. The IRS takes missing 1099s seriously because it affects their ability to match income reports. Don't let them off the hook - their "accounting system issues" excuse doesn't hold water legally. Keep pushing them for the proper documentation while filing with your own records. You're doing everything right by reporting the income regardless of their failures.