Just wanted to add something that might help with your cash flow situation - if you're able to make any 2025 HSA contribution now (even a small amount), you could potentially use it to reimburse yourself for the ER visit immediately. Then throughout the year, you can continue making contributions up to your annual limit to build up the account for future expenses. Also, don't forget that HSA funds can be used for more than just hospital bills - things like prescription medications, medical equipment, and even some over-the-counter items with a prescription can be reimbursed. I'd recommend checking your HSA provider's list of qualified expenses since it's broader than many people realize. Hope your recovery from the ER visit goes smoothly!

I'm sorry to hear about your ER visit - that's always stressful, especially when finances are tight! You're absolutely right about the HSA contribution deadline being April 15th, regardless of filing extensions. Unfortunately, that window has closed for 2024 contributions. However, there are a few strategies that might help your situation: First, as others mentioned, you can contribute for 2025 and use those funds immediately for your current medical expenses. Second, if you have any documented medical expenses from previous years that you paid out-of-pocket (after your HSA was established), you could reimburse yourself for those instead and save your current cash. One thing to consider for the future - many people find it helpful to contribute to their HSA early in the year or through regular payroll deductions to avoid this timing crunch. Also, if your employer offers an HSA match or contribution, make sure you're not leaving any free money on the table. The silver lining is that once you do make 2025 contributions, you can use those funds right away for your medical expenses, even though the tax benefit won't show up until you file next year. Keep all your receipts and documentation - you'll need them for tax purposes and potential audits.

Just a practical tip from someone who's had an S corp for 6 years - I set up a separate savings account where I transfer a percentage of all business income that passes through to me. This way I always have the cash ready for my personal quarterly estimated payments.

Great question! You're absolutely correct that S corporations are pass-through entities, so the business itself typically doesn't make federal income tax estimated payments. Instead, you'll handle those on your personal return (Form 1040-ES) for your share of the business income. However, don't forget about payroll taxes if you're on payroll! As an S corp owner-employee, you need to pay yourself a reasonable salary and make federal tax deposits for employment taxes (Social Security, Medicare, and income tax withholding) - but these follow different schedules than quarterly estimated payments. One quick tip: make sure to check your state requirements too, as some states do require S corps to make estimated payments at the entity level. And consider setting aside a percentage of your pass-through income in a separate account so you're always ready for those quarterly deadlines. Good luck with your first year as an S corp!

This thread has been incredibly helpful! I'm dealing with a CP140 notice myself (just received it yesterday) and I'm taking notes on everyone's strategies. One question I haven't seen addressed yet - for those who successfully got interest or penalties removed, how long did the whole process take from start to finish? I'm trying to decide whether to pay immediately to stop additional interest from accruing, or wait to see if I can get some relief first. Also, did anyone run into issues with the IRS claiming they DID send previous notices even when you have proof you didn't receive them? I'm worried about getting into a "he said, she said" situation where they insist notices were sent but I have no way to prove I didn't get them.

I want to add one more resource that hasn't been mentioned yet - the Taxpayer Advocate Service (TAS). If you're having trouble getting the IRS to respond to your requests or if you're facing financial hardship because of this situation, you can contact TAS at 1-877-777-4778. They're an independent organization within the IRS that helps taxpayers resolve problems when normal channels aren't working. TAS can be particularly helpful if you're dealing with systemic issues like notices going to wrong addresses repeatedly, or if the IRS isn't responding to your abatement requests within reasonable timeframes. They have the authority to issue Taxpayer Assistance Orders that can stop collection actions while your case is being reviewed. I used TAS last year when the IRS kept insisting I owed money that I had already paid, and they were able to get everything sorted out within a few weeks when my own calls and letters weren't getting anywhere. It's a free service and they really advocate for you against the IRS bureaucracy. Worth keeping in your back pocket if the standard approaches don't work out.

I just completed this exact process for my S-Corp last year and wanted to add a few practical tips that might help! You're definitely on the right track with Form 1128, and the automatic approval route for S-Corps switching to calendar year is pretty straightforward once you understand the timeline. One thing I wish someone had told me earlier: start gathering your documentation now, even though you won't file Form 1128 until 2026. You'll need your articles of incorporation, S-Corp election forms, and previous tax returns as supporting documents. Having these organized ahead of time made the actual filing much smoother. Also, consider setting up a separate folder or file for tracking the transition. You'll be dealing with three different tax periods during this change: your final August 2025 fiscal year return, the short-year return for September-December 2025, and then your first full calendar year return for 2026. Keeping everything organized by period helped me avoid mixing up deadlines and requirements. One last suggestion: if you're planning to do this yourself, consider at least having a tax professional review your Form 1128 before filing, even if you complete it yourself. The automatic approval process is reliable, but getting it right the first time saves you from potential delays or IRS questions later. The peace of mind was worth the consultation fee for me!

I just went through this exact same process for my LLC with S-Corp election earlier this year, and I totally understand the confusion about Form 1128 deadlines! The IRS instructions really are written like they assume you already know what you're doing. Here's what I learned after digging through Revenue Procedure 2006-45: You qualify for automatic approval under Section 6.02 since you're switching FROM fiscal year TO calendar year as an S-Corp. The key is that you haven't used this automatic procedure in the past 48 months, which you haven't since you've been filing fiscal year since 2022. For timing, you DON'T need to file Form 1128 before your new tax year begins. Instead, you file it by the due date of your FIRST return under the new tax year. So if you want to switch to calendar year starting January 1, 2025, you'd file Form 1128 by March 15, 2026 (or September 15 with extension). The form itself is actually pretty manageable once you know you're doing automatic approval - you skip Part II entirely and focus on Parts I and III. For the business purpose, something simple like "to simplify tax compliance and align with calendar year operations" works fine. One heads up: you'll need to file a short-year return for your transition period (September 1 - December 31, 2025), which has its own deadline and requires some annualization calculations. Most tax software handles this, but it's worth double-checking those calculations. Good luck with the switch - it's definitely worth it to get everything aligned on calendar year!

FYI: Make sure you understand the new 1099-K thresholds. They were supposed to drop to $600 but the IRS pushed it back. For 2023 (filing in 2024), the threshold is $20,000 AND 200 transactions. For 2024 (filing in 2025), it's $5,000. So if you sold $5300 worth of gear in 2023, you might not even get a 1099-K unless you also had 200+ separate transactions! Worth checking the current rules before worrying too much.

As someone who's been through this exact situation, I can confirm what others have said - the 1099-K is just a reporting document, not a tax bill. I sold around $4,200 worth of music gear last year and was initially panicked about the tax implications. The reality is that most musicians selling personal gear are doing so at a loss. I kept a simple spreadsheet tracking what I originally paid versus what I sold each item for. Out of 15 items sold, only 2 vintage pedals actually sold for more than I paid originally - those were the only ones that generated taxable income. My advice: Start documenting everything now. Even if you don't have original receipts, gather what you can - credit card statements, emails, or research what those items typically cost when you bought them. The IRS understands that people don't keep receipts for personal items forever, but you need to make a reasonable effort to establish your cost basis. Also, don't forget that any improvements or modifications you made to the gear can be added to your original cost basis, which further reduces potential taxable gains.