I messed up my taxes last year and ended up owing a ton. I just paid as soon as I found out because the interest really adds up! But now I'm wondering if anyone knows a good tax software that warns you about potential underpayment penalties BEFORE you file?

Great question! Yes, paying earlier definitely saves you money. The IRS charges interest daily on unpaid balances, so every day counts. At the current 8% annual rate, that's roughly 0.022% per day - which adds up fast on larger amounts. I learned this the hard way a few years ago. Had a $12,000 balance and thought I'd be smart waiting until April 15 to pay. Those extra two months cost me about $200 in additional interest that I could have easily avoided. One thing to keep in mind though - if you're short on cash, make sure paying early won't put you in a bind elsewhere. The IRS offers reasonable payment plans if needed, and sometimes it's better to pay what you can now and set up an installment agreement rather than drain your emergency fund completely.

I'm new to this community but have been dealing with the exact same nightmare! I've been trying to reach the IRS for over 5 weeks about a dependent filing issue and have called at least 20 times with zero success. The automated system is absolutely maddening - I've literally thrown my phone across the room in frustration multiple times. Reading through all these strategies has been like finding a treasure trove of hope! The 7 AM partial SSN method that @Issac Nightingale shared sounds incredibly promising - I'm definitely setting multiple alarms to try this tomorrow morning. The fact that so many people have had success with this specific technique gives me actual optimism for the first time in weeks. What really gets me is that we've had to become expert code-breakers just to access basic taxpayer services. The existence of paid services like Claimyr really highlights how fundamentally broken this system is. It's honestly shameful that our government agency is so inaccessible that an entire industry has sprung up just to help people reach them. I'm also going to try the Taxpayer Advocate Service route if the morning call doesn't work out. Thank you everyone for sharing these hard-won insights - this community is literally saving people's sanity! I'll report back on how the 7 AM method works for me.

I'm new to this community but desperately needed to find this thread! I've been battling the IRS phone system for 3 weeks trying to resolve an issue with my business tax return filing. After reading through all these incredible strategies, I feel like I finally have a roadmap that might actually work. The 7 AM partial SSN method that @Issac Nightingale shared is absolutely brilliant - I never would have thought to enter just part of the SSN and then wait for the system to give up. I'm setting my alarm for 6:55 AM tomorrow to try this approach. The consistency of success stories with this method is really encouraging after weeks of complete failure with traditional calling approaches. What strikes me most is how this community has essentially had to reverse-engineer basic government services through collective problem-solving. It's both impressive and deeply troubling that we need these workarounds just to exercise our right to speak with the IRS about our own returns. For anyone else dealing with business tax issues specifically - I've learned to have my EIN, all relevant forms, and a written list of specific questions ready. From what I've gathered here, being super organized when you finally get through can make all the difference in actually resolving the issue on that call. Thank you to everyone who has shared their hard-won strategies here. This thread is literally a lifeline for people trapped in automated system hell!

Small tip that saved me once - check your email from around the time you filed last year. Sometimes confirmation emails from Free Fillable Forms or the IRS have useful reference numbers or confirmation details that can help expedite getting copies. Also, if your refund was direct deposited, check your bank statements from that time period - the exact refund amount can sometimes help your tax preparer cross-reference and confirm your AGI.

Don't panic! You're definitely not alone in this situation. I made the exact same mistake a few years back with Free Fillable Forms - it's surprisingly common since they don't automatically save or email your completed returns. Here's the good news: your tax preparer likely doesn't need the actual return copies to complete your 2024 taxes. The main things they need are your prior year AGI (Adjusted Gross Income) and any carryover items like capital losses or charitable contribution carryovers. If you have your W-2s, 1099s, and other tax documents from last year, an experienced preparer can calculate your AGI pretty accurately. For the official documentation, definitely start with the free IRS transcript online at irs.gov/transcripts - it's immediate if you can verify your identity online. For DC, try MyTax.DC.gov first before calling. The April 15th deadline is definitely doable! Your preparer can work with what you have now and you can get the official transcripts for your records later. The key is having those income documents from 2023, which it sounds like you do have.

One thing I'd add for anyone reading this - make sure you elect to deduct startup costs on your tax return! The IRS doesn't automatically give you this deduction. You need to attach a statement to your first-year return (or file an amended return) making the Section 195 election to deduct startup costs. Without this election, all your startup costs would have to be amortized over 15 years instead of getting that nice $5,000 first-year deduction. I almost missed this when I started my LLC because my tax software didn't prompt me about it. Had to go back and amend my return to claim the election. The statement just needs to say something like "Election under Section 195 to deduct startup costs" and list the costs and amounts. Worth double-checking with a tax professional if you're not sure, but don't let this slip through the cracks!

This thread has been incredibly educational! I'm planning to start a single-member LLC for my graphic design business and was getting completely overwhelmed by conflicting information online. The clarification about the $50,000 threshold (not $5,000) for when the deduction starts getting reduced is huge - I was seriously considering not starting my business because I thought I'd lose all deductions if I went over $5,000. One follow-up question: If I have startup costs in 2024 but don't actually start generating revenue until 2025, do I still claim the startup cost deduction on my 2024 return? Or does it go on the 2025 return when the business "officially" begins operating? I'm planning to spend about $4,200 on logo design, website development, business formation, and some initial marketing materials before launching in early 2025. Also really appreciate the reminder about the Section 195 election - definitely something I would have missed without this discussion!

My tax advisor gave me conflicting information on this last year! She said my spouse needed to show at least some profit from self-employment for us to use my Dependent Care FSA. We ended up not using the FSA and just took the tax credit instead, which worked out better for us anyway since we have 2 kids and high childcare costs. Have you compared whether the FSA or the tax credit would be better in your situation? Sometimes the tax credit can be more beneficial, especially if your spouse might have little/no income.

I went through this exact situation when my husband started his consulting business in 2022. The key thing I learned is that the IRS doesn't require a minimum profit amount for your spouse to be considered "gainfully employed" for Dependent Care FSA purposes. What matters is that they have a legitimate business with profit intent. Even if your spouse shows a loss in 2023 due to startup costs, as long as they're genuinely operating a business (keeping records, spending time on it, marketing, etc.), they qualify as self-employed. However, your FSA contribution limit will be capped at their net earnings for the year. One thing to consider: if your spouse expects to have minimal or negative income in the year you want to use the FSA, you might want to compare the FSA benefit against taking the Child and Dependent Care Credit instead. The credit doesn't have the same earned income limitation and might be more beneficial in your situation. Also, make sure your spouse keeps detailed business records - receipts, time logs, business plan, etc. This documentation will be crucial if the IRS ever questions whether it's a legitimate business versus a hobby. Good luck with the new business venture!