19 Has anyone considered just waiting until filing your 2024 tax return and paying everything then? I missed my Q4 payment too, but my accountant said sometimes it's simpler to just pay the small penalty rather than jumping through hoops to make a late estimated payment separately.

23 Another option if you're having trouble with the IRS website is to make the payment by phone. You can call 1-888-PAY-1040 (1-888-729-1040) and make your late Q4 2024 estimated payment over the phone. There's usually a small convenience fee (around $2-3), but it might be worth it to avoid the website navigation issues. When you call, tell them you want to make a 2024 estimated tax payment, and they should be able to process it properly. They can also confirm that your payment is being applied to the correct tax year, which gives you peace of mind that it won't get mixed up with 2025 payments. I've used this method before when the website was being glitchy, and it's usually pretty straightforward. The automated system walks you through everything step by step.

For what it's worth, I just talked to my CPA about this exact issue. She said the IRS has been accepting consolidated spreadsheets for crypto transactions for years now. She recommended submitting one Form 8949 with the total amounts and checking the box indicating attached statements, then include the Excel data as supporting documentation.

I went through this exact same nightmare last year with about 8,500 crypto transactions. After trying multiple approaches, here's what worked best for me: I ended up using a combination approach - I used Koinly to import and organize all my transactions (it handled the API connections for major exchanges and CSV uploads for smaller ones), then exported everything to a properly formatted spreadsheet that matched Form 8949 columns exactly. The key things I learned: 1. Yes, the IRS absolutely accepts attached spreadsheets for large transaction volumes - it's actually their preferred method over printing thousands of form pages 2. Format your spreadsheet with the exact same column headers as Form 8949 (Description, Date Acquired, Date Sold, Proceeds, Cost Basis, Adjustment Code, Gain/Loss) 3. On the actual Form 8949, check box C and write "See attached statement" then enter your totals on line 2 4. Include your name, SSN, and "Supplement to Form 8949" on every page of your spreadsheet The IRS processing center actually thanked me in a follow-up letter for providing such clear documentation. Don't panic - this is way more common than you think and the IRS has standard procedures for handling it. You've got this!

Has anyone else gotten confused about the ordering of NOL usage? My understanding is that you have to use the oldest losses first, but our tax software seems to be applying them differently.

I'm dealing with a similar situation as a new startup owner. One thing that helped me understand this better was realizing that Form 1120 line 29a is specifically for the NOL deduction you're claiming in the CURRENT year, not just tracking your total accumulated losses. Since you have negative taxable income again this year, you won't enter anything on line 29a because there's no positive income to offset. But you're absolutely building up your NOL carryforward balance - you'll have $42,000 from year 1 plus your new $38,000 loss from this year. The key is maintaining good records of these accumulated losses. I keep a simple schedule that tracks each year's NOL separately because when you eventually become profitable, you'll need to apply them in the correct order (oldest first) and follow the 80% limitation rule for post-2017 losses. Don't worry - you're not missing out on any tax benefits by not using the NOLs now. They'll be there waiting for you when your startup starts generating taxable income!

Just wanted to add that you should definitely keep track of your mileage for each app separately! I made the mistake of just tracking total miles last year without noting which app I was driving for. Even though you'll put everything on one Schedule C, having that breakdown by platform can be really useful for seeing which gigs are actually profitable after expenses. I found out I was actually LOSING money on some Doordash orders once I factored in gas and depreciation, but making decent money on Uber Eats. Changed how I prioritize which orders to accept.

In addition to what others have said, make sure you're tracking ALL your expenses, not just mileage! I do all these delivery apps too and was leaving money on the table my first year. Deductible expenses: - Phone bill (% used for gig work) - Phone holder/mount for car - Hot bags (if you bought your own) - Portion of car insurance - Parking fees while waiting for orders - Dashcams (safety equipment) - Cleaning supplies for your car - Masks, hand sanitizer, etc. If you use the actual expense method instead of standard mileage rate, you can also deduct gas, maintenance, repairs, etc., but usually the standard mileage rate is better.

I went through this exact same nightmare with my LLC's S-corp election last year. The IRS "lost" my fax too, despite having clear transmission records. Here's what worked for me: I created a detailed timeline document showing every step I took - original fax date, confirmation receipt, follow-up calls, etc. Then I attached this timeline to my explanation letter along with all my proof of transmission. I made it crystal clear that I had met the 75-day deadline and this was their processing error, not mine. The key thing that helped was being very specific about dates and referencing the "reasonable cause" provisions. I sent everything via both certified mail AND e-fax (used eFax.com which gives great delivery confirmations). Got my acceptance letter about 6 weeks later with no penalties. One tip: when you call to follow up, ask specifically for the "Business Entity Control" department - they're the ones who actually process Form 2553. The general customer service reps often can't see these submissions in their system, which is why they keep saying it wasn't received. Stay persistent but polite. You did everything right - don't let them make you feel like this is your fault!

I'm dealing with a similar situation right now with my LLC's S-corp election! The IRS lost my fax submission too, despite having proof of transmission. I was panicking about the 75-day deadline until I read through all these responses. Based on what everyone's shared here, I'm planning to follow the dual submission approach - both certified mail with return receipt AND e-fax. I'm also going to create that detailed timeline document someone mentioned showing all my original filing dates and proof. One question though - has anyone had success getting through to the Business Entity Control department directly, or do you have to go through regular customer service first? I've been on hold for hours multiple times and keep getting transferred around. Also, for those who used services like Claimyr to get through to the IRS - was it worth the cost? I'm tempted to try it just to get a definitive answer on whether they have any record of my original submission. Thanks to everyone for sharing their experiences - this thread has been incredibly helpful for understanding I'm not alone in this mess!