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CyberSamurai

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Great thread with lots of helpful information! I just completed my Form 706NA payment process last week and wanted to share a few additional tips that might help others: 1. Double-check your bank account information before submitting - I made a typo in my routing number initially and had to start over. The IRS system caught it during verification, but it delayed my payment by several days. 2. If you're making a large payment (like the $34,500 mentioned in the original post), some banks have daily ACH limits that might prevent the transaction from going through. I had to call my bank to temporarily increase my limit for the estate tax payment. 3. Keep multiple copies of your confirmation page and save it as a PDF. I printed three copies and emailed the PDF to myself as backup. The confirmation number is crucial if you ever need to trace the payment. The whole process was actually smoother than I expected once I figured out the right options to select. The key is just being very careful about the tax year selection (as Vanessa mentioned) and making sure all your information is exactly correct before hitting submit.

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Chloe Zhang

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Thanks for these practical tips! The bank daily limit issue is something I never would have thought about. I'm dealing with a similar situation where the estate owes around $28,000, and my bank does have ACH limits. Did you have to provide any special documentation to your bank to increase the limit temporarily, or was it just a phone call? I want to make sure I have everything ready before I attempt the payment since I'm already cutting it close to the deadline.

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Anna Stewart

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@CyberSamurai For my bank, it was just a phone call to their business banking department (since I was acting as executor). I explained that I needed to make a one-time IRS estate tax payment and they temporarily raised my ACH limit for 48 hours without any additional documentation. However, different banks have different policies - some might require you to provide a copy of your letters testamentary or proof that you're the authorized representative for the estate. I'd recommend calling your bank a day or two before you plan to make the payment, just to be safe. Some banks can make the change immediately over the phone, while others might need 24 hours to process the limit increase. Given that you're close to the deadline, definitely don't wait until the last minute to sort this out! Also, if your bank gives you any trouble, you could consider using a wire transfer instead, though that typically comes with higher fees. The important thing is getting the payment submitted on time.

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Ava Garcia

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I went through this exact process about 6 months ago and can confirm that the Direct Pay method works well for Form 706NA. One thing that really helped me was calling the IRS taxpayer assistance line beforehand to confirm I was selecting the right options - they verified that using "Form 706" in the system covers both regular 706 and 706NA filings. A few additional tips from my experience: - Make sure you have the estate's EIN ready before starting the payment process - The system will ask for the "primary taxpayer" - use the decedent's name exactly as it appears on the 706NA form - If you're making the payment close to the due date, consider doing it in the morning rather than late at night to avoid any potential system maintenance windows The confirmation email came through within about 10 minutes, and I was able to track the payment status through my bank. The whole process took less than 15 minutes once I had all the information ready. Don't stress too much about it - the IRS payment system is actually pretty straightforward once you know which buttons to click!

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This is really helpful, thank you! I'm just starting this process and feeling overwhelmed. Quick question - when you called the IRS taxpayer assistance line, how long did it take to get through? I've been dreading having to call them because I keep hearing horror stories about multi-hour wait times. Did you have any specific number you called or just the general taxpayer assistance line? I want to get confirmation before I submit my payment too, but I'm worried about spending my whole day on hold.

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Ezra Collins

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Just want to add that I had a similar massive refund one year ($18k when I normally got $1-2k) and I filed it without questioning because, hey, free money right? BIG MISTAKE. Two years later I got hit with an audit, had to pay back the entire amount PLUS penalties and interest. Ended up owing over $23k and it destroyed my finances for years. Don't mess with the IRS. If something seems fishy, it probably is.

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Were you able to go after the tax preparer for the penalties? Shouldn't they be liable for their mistakes?

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This is exactly why I always tell people to be extremely cautious with new tax preparers, especially when they promise unusually large refunds. What you're describing sounds like classic "ghost preparation" tactics where preparers manufacture deductions and credits to inflate refunds. The -$35,000 "additional income" combined with $30,000 in credits is a huge red flag. These numbers suggest your preparer may be claiming fake business losses or inappropriate refundable credits like the Earned Income Tax Credit that you don't actually qualify for. My advice: DO NOT file this return. Get copies of everything your preparer did and take it to a reputable CPA or enrolled agent for a second opinion. Ask them to explain every single line item that's different from your previous returns. Also document everything about your interactions with this preparer - you may need it if you decide to report them to the IRS. The fact that she's giving you conflicting refund amounts ($25k vs $35k) is another major warning sign. Better to get a legitimate smaller refund than deal with years of IRS problems, penalties, and having to pay back fraudulent refunds with interest.

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This is such solid advice. I'm actually dealing with something similar right now - my preparer is claiming I qualify for credits I've never heard of before. The whole "trust me" response when you ask for documentation is the biggest red flag possible. One thing I'd add is to make sure you get copies of ALL the forms before you leave the preparer's office. Don't just take their word for what's on the return. I learned this the hard way when my preparer claimed certain deductions were "standard" but couldn't show me where they came from when I asked later. @f014fc63b237 You're smart to question this now rather than after filing. The peace of mind from getting a second opinion is worth way more than any potential refund.

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Yuki Tanaka

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The actual stats on audit rates might make you feel better. For small Schedule C filers (under $100k), the audit rate is around 0.9%. Even with multiple years of losses, unless you have other major red flags, your chances remain relatively low. Make sure you can document that your expenses were legitimate business costs, not personal expenses, and you should be okay.

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Thanks for sharing those stats - that does make me feel better. Just curious, where did you find those numbers? And what would be considered other "major red flags" besides the consecutive losses?

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Yuki Tanaka

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I got those stats from the IRS Data Book which they publish annually. The latest numbers show small business audits have been declining due to IRS budget constraints, though that may change with recent funding increases. Major red flags beyond consecutive losses include unusually large deductions compared to income (especially home office, vehicle, travel, meals), round numbers that suggest estimation rather than actual record-keeping, substantial cash-based income, and claiming 100% business use for vehicles. Also, mathematical errors or inconsistencies between forms can trigger automated reviews that sometimes escalate to audits.

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Carmen Ortiz

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Has anyone here actually been audited for a small business with losses? I'd love to hear a firsthand experience about what happened and how it went.

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I was audited back in 2023 for my crafting business that had losses for 4 years. It was a correspondence audit (mail only). They asked for receipts for all my expenses and evidence it was a real business (website screenshots, business cards, show applications). It was stressful but I had good records and they accepted everything. Whole process took about 5 months.

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Ravi Malhotra

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That's really helpful to hear from someone who actually went through it! Five months sounds like a long time but at least it was just correspondence and not an in-person audit. Did they question the legitimacy of your business being a "real" business versus a hobby, or did they focus more on the specific expense deductions? I'm trying to figure out what kind of documentation would be most important to keep organized.

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WARNING: Be careful about reasonable cause. My husband tried this last year for his consulting business and it got REJECTED. He had to file as a sole prop for half the year and then as an S-corp, which meant TWO different tax returns and a ton of accounting headaches. The IRS is getting stricter about these late elections. Make sure your reasonable cause is actually reasonable and not just "I didn't know about it." We learned the hard way that "I was busy with client work" isn't good enough. If you're serious about making this work, talk to an actual tax pro who specializes in business formation, not just random internet advice.

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What kind of reasonable cause statement did your husband use that got rejected? Might help the OP avoid the same mistake.

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QuantumQuest

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I went through this exact situation 2 years ago as a freelance web developer. Here's what I wish someone had told me upfront: The timing is crucial, but you have more flexibility than you might think. You can form your LLC in August and still get S-corp treatment for your entire 2023 income, BUT you need to act fast once the LLC is formed. My recommendation: Form the LLC immediately in August, get your EIN the same day (you can do this online), then file Form 2553 within 2-3 weeks. Even if you're technically "late" by a few days, a simple reasonable cause statement explaining you're a first-time business owner unfamiliar with the election deadlines will likely be accepted. The key advantage is that once approved, you'll file a single 1120-S for the entire year instead of splitting between Schedule C and S-corp returns. This saves you significant accounting complexity and costs. One important note: Make sure you have reasonable justification for the salary vs. distribution split once you're an S-corp. The IRS expects you to pay yourself a "reasonable" salary for the work you do, with the remaining profits taken as distributions (which aren't subject to self-employment tax). Don't overthink this - thousands of freelancers make this transition successfully every year. Just don't wait until December to start the process!

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Ava Kim

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This is really helpful advice! I'm also a freelancer (marketing consultant) and have been putting off the LLC formation because the timing seemed so complicated. Your point about acting fast once the LLC is formed makes total sense. Quick question - when you say "get your EIN the same day," do you mean online through the IRS website directly? I've seen some services that charge fees for EIN applications, but it sounds like you did it yourself for free? Also, did you run into any issues with quarterly estimated taxes during the transition year, or does the S-corp election smooth that out too?

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Talia Klein

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Just wanted to add some perspective as someone who's been doing gig work for a while - the tax situation isn't as scary as it seems once you get organized! The key is treating this like a real business from day one. I use a simple spreadsheet to track my daily earnings, miles driven, and any expenses. At the end of each week, I calculate roughly 30% of my profit and transfer it to a separate "tax savings" account. For tracking mileage, I highly recommend using an app like Stride or MileIQ that automatically tracks your drives. Manual tracking gets tedious and you'll inevitably forget to log trips. One thing that surprised me: even though you're paying self-employment tax (which feels like a lot), you're also earning Social Security credits that count toward your future benefits. So it's not just money disappearing - you're building toward your retirement too. The $600 threshold just determines whether DoorDash sends you a 1099 form, but you're technically required to report ALL income regardless of whether you get a form. Keep good records and you'll be fine!

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This is really helpful advice! I'm new to gig work and the automatic mileage tracking apps sound like a lifesaver. Quick question - when you say "profit" for the 30% calculation, do you mean total earnings minus just mileage deduction, or should I subtract other business expenses too before calculating what to set aside for taxes? Also, I hadn't thought about the Social Security credits aspect - that actually makes the self-employment tax feel less painful knowing it's contributing to future benefits. Thanks for putting it in perspective!

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Amina Diallo

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Great question! When I calculate the 30% to set aside, I use my profit after ALL business expenses - so total earnings minus mileage deduction, phone bill percentage, equipment costs, etc. This gives you a more accurate estimate of your actual taxable income. For example, if you earn $500 in a week but have $150 in mileage deduction and $20 in other business expenses, your profit is $330. I'd set aside about $100 (30% of $330) for taxes rather than $150 (30% of $500). The apps make such a difference! I tried manual tracking for like two weeks and kept forgetting to start/stop the timer. Now it just runs automatically when I'm driving and I can categorize trips later. Much less stressful than trying to recreate your mileage from memory at tax time. And yes, the Social Security angle really changed my perspective too. As gig workers we're essentially self-employed business owners building our own retirement credits. Makes the extra tax burden feel more like an investment in your future rather than just money going down the drain!

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GalaxyGazer

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As someone who's been dashing for about 8 months, I'd say it's definitely worth it if you approach it right from the start. Here's what I wish someone had told me when I was at your stage: First, don't stress too much about the $600 threshold - others have explained it well, but just know you're still a ways from hitting it based on your current earnings. What I found most helpful was setting up systems early: 1. Download a mileage tracking app immediately (I use Stride - it's free and designed for gig workers) 2. Open a separate savings account just for taxes and transfer 25-30% of your weekly profit there 3. Keep a simple log of any equipment you buy (phone mount, insulated bags, etc.) The tax situation seems overwhelming at first, but it's really manageable once you get organized. I actually ended up owing less than I expected because the mileage deduction is pretty generous - I drive about 70% of my total earnings in deductible miles. One tip: don't just focus on gross earnings when deciding if it's "worth it." Track your profit after expenses for a few weeks to see your real hourly rate. That'll help you decide if you want to continue and which times/areas are most profitable for you. You're smart to think about this stuff early rather than scrambling at tax time like a lot of people do!

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Salim Nasir

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This is such solid advice! I'm in a similar situation as the original poster - just started doing delivery work and feeling overwhelmed by all the tax stuff. The separate savings account idea is brilliant - I keep telling myself I'll set money aside but never actually do it. Quick question about the mileage tracking - does Stride track automatically or do you have to remember to turn it on each time you start dashing? I'm worried I'll forget and mess up my records. Also, when you say 70% of earnings in deductible miles, does that include driving TO the restaurant areas at the start of your shift, or just the actual delivery miles? Thanks for breaking this down in such a practical way. Makes it feel way less intimidating!

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Zoe Wang

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@d73f89d17d35 Great advice! Just wanted to add that Stride does track automatically once you set it up - it uses your phone's GPS to detect when you're driving and categorizes trips. You can always edit/classify them later if needed. For deductible miles, you can actually deduct ALL business-related driving - so yes, that includes driving TO your first restaurant, between deliveries, AND driving home from your last delivery if you wouldn't have been in that area otherwise. The key is that it has to be for business purposes. I keep a simple rule: if I'm driving because of DoorDash (getting to hotspots, between orders, etc.), I count those miles. Personal detours obviously don't count, but most of your driving during a dash session will be deductible. The separate account thing really is a game-changer. I set up an automatic transfer so every Sunday I move my "tax money" over. Takes the guesswork and willpower out of it!

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