Don't overlook the power of bank feeds! Whatever bookkeeping software you choose, make sure your business bank account connects directly to it. This automated data flow changed everything for us. We use Xero + Mercury Bank and they integrate perfectly. Transactions show up automatically, most are categorized correctly, and I just review things weekly instead of doing manual entry. Takes me about 15 minutes a week to stay on top of our books now. Also, PLEASE use a receipt capturing app from day one! We didn't and had to go through credit card statements trying to remember what each purchase was for. Total nightmare. Most bookkeeping software has a mobile app that lets you snap photos of receipts immediately.

For cash expenses, I'd recommend setting up a petty cash system with proper documentation. Keep a small lockbox with a set amount (like $200-300), and create a simple log sheet where you record every cash expenditure with date, amount, vendor, and business purpose. Take photos of any receipts immediately. Most importantly, "reimburse" yourself from petty cash by writing a business check to replenish it back to the original amount. This creates a clear paper trail that your bookkeeping software can track. When you write the replenishment check, categorize it by breaking down what the cash was actually spent on (office supplies, meals, etc.) rather than just "petty cash." Another option is to minimize cash transactions altogether - many vendors who claim to only take cash will actually accept Zelle, Venmo for Business, or other digital payments that still create records. Even if there's a small convenience fee, it's often worth it for the automatic documentation. The key is treating cash expenses with the same rigor as card transactions - document everything immediately before you forget what it was for!

The most important question nobody's asked: what's your approximate income level? The answers will be very different if you're making $35k vs $135k. At lower income levels, Head of Household plus a dependent can absolutely result in zero federal tax liability.

I work in payroll for a mid-sized company and see this situation fairly often. What you're experiencing is actually a feature, not a bug! The withholding system is designed to be precise based on your individual tax situation. As Head of Household with one dependent, you get a higher standard deduction ($21,900 for 2025) plus potentially the full Child Tax Credit ($2,000). If your income falls within certain ranges, these benefits can completely offset your federal tax liability. A few things to keep in mind: 1) Make sure your W-4 accurately reflects your situation - if you moved in with a partner or your child aged out, your status might change, 2) The IRS withholding calculator is your best friend - run it quarterly if your situation is stable, and 3) Consider setting aside a small emergency fund for taxes anyway, just for peace of mind. Your coworker likely files Single with no dependents, so her withholding will look completely different even at the same salary. This is totally normal!

Pro tip: calling early morning right when they open has worked best for me to actually get through to someone

I went through this exact same situation last year. The 570/971 combo is frustrating but pretty common. In my case, it was because the IRS needed to verify my identity since I had moved and changed jobs. The letter took about 3 weeks to arrive and once I responded with the requested documents, my refund was released within 10 days. Hang in there - I know it's stressful when you're counting on that money for bills. Keep checking your mail daily and your transcript for any updates.

I see a lot of detailed responses here already but wanted to add that timing matters too. If you formally dissolved your sole proprietorship and formed the LLC as a completely separate entity with new EIN, business accounts, etc., you might have a stronger case for treating it as a new business eligible for startup costs rather than just organizational costs. Did you completely close out the sole prop and start fresh, or was it more of a conversion? That distinction can matter for how the IRS views it.

That's exactly the right approach, Khalil! Since you kept the same EIN and it's a single-member LLC taxed as a disregarded entity, the IRS will definitely view this as a continuation of your existing business rather than a startup. Your $6,700 in formation costs should be treated as organizational expenses under Section 248. You can deduct $5,000 immediately and amortize the remaining $1,700 over 15 years (about $113 annually). Make sure to keep detailed records separating the LLC formation costs (legal fees, state filing fees, operating agreement drafting) from any regular business expenses you might have incurred during the transition. One tip: if you had any costs related to transferring assets from the sole prop to the LLC (like updating contracts or transferring licenses), those might be treated differently than the pure organizational costs, so keep those receipts separate as well.

Mine just hit my account!!! I had the same DDD of 2/24 with H&R Block and was getting so worried! I literally just checked my account after obsessively refreshing all day and it's there! I'm so relieved! I was starting to think something had gone wrong with my return. Check your accounts now - they might be processing a batch right now!

Just wanted to share an update for anyone still waiting! I had the same DDD of 2/24 with H&R Block and mine finally showed up this morning around 6:30 AM. Based on what I'm seeing here and from talking to others, it looks like H&R Block is definitely processing these in waves rather than all at once like they used to. For what it's worth, I used the Refund Transfer option (where they take fees out of the refund) and bank with a smaller regional credit union. The timing seems pretty random this year - some people got theirs days early, others right on the DDD, and a few are still waiting even past their date. @Zoe - since you need those funds for your flight next week, you might want to call H&R Block directly with your confirmation number. They can sometimes see if there are any holds or processing issues on their end. Also, if you're really in a pinch, some banks will provide a provisional credit if you can show them the DDD documentation, though that varies by institution. Hope this helps ease some anxiety for everyone still refreshing their accounts!