Does CashApp Taxes have an option to include a written explanation with your tax return? I have a similar issue but with Etsy sending me a 1099-K for personal items I sold at a loss.

Yes, CashApp Taxes does have an option to add explanations or notes to your return. When you're in the final review stage before filing, there should be a section for "Additional Information" or "Notes" where you can add explanations for unique situations. For your Etsy situation, you'd want to note that these were personal items sold at a loss, not a business activity, which is similar to the original poster's reimbursement scenario. CashApp Taxes isn't as robust as some paid options, but it handles most common situations pretty well if you know where to look for these features.

I've tried both TurboTax and H&R Block for this exact issue. TurboTax actually has a clearer interface for handling incorrect 1099-Ks. It lets you specifically mark personal payments vs business income. H&R Block works too but requires more clicking around to find the right options.

In my 401k I've been using a treasury fund for cash parking and it's currently yielding about 3.8% which beats most stable value funds I've seen. The advantage of treasuries in the current environment is they respond faster to rate changes. The downside is there can be some minor NAV fluctuation vs stable value funds which maintain stable principal.

Thanks for that insight! Do you see much day-to-day fluctuation in the NAV with your treasury fund? I'm pretty conservative with this portion of my savings so stability is important, but that extra 0.7% yield is pretty significant too. I'm guessing the stable value fund will eventually catch up to current rates, but seems like they lag quite a bit based on what you're saying.

Money market funds are solid for cash parking in retirement accounts. The 4.2% yield is quite good actually. The main thing to check is the expense ratio - some 401k plans offer money market funds with ridiculous fees that eat into that headline yield. Also, if you don't mind sharing, which fund is offering 4.2%? Most I've seen are in the 3.5-3.8% range.

Thanks for the tip about the state refund! I didn't even think about that. I'm expecting about $700 back from my state, so that would definitely help reduce what I need to finance. Based on everyone's advice, I think I'll make a payment now of whatever I can afford and then set up a short-term payment plan. Seems like the consensus is not to wait until April 15th!

You're welcome! Yes, using your state refund toward your federal tax debt is a smart move. And definitely don't wait until April - not only will the phone lines be jammed, but you'll be accruing interest on the full amount in the meantime. One more tip: if you set up a payment plan but then find you can pay it off faster than expected, there's no penalty for paying early. I ended up getting a small bonus at work and was able to clear my tax debt in 3 months instead of the 6 I had planned for.

Offers in Compromise are pretty hard to get approved. The IRS only accepts them if they genuinely believe they cannot collect the full amount from you either now or in the foreseeable future. You have to provide extensive documentation of your assets, income, expenses, etc. For a tax debt of $7,420 like the OP has, it's unlikely to be worth pursuing unless they're facing severe financial hardship. The application fee alone is $205 (though it can be waived for low-income taxpayers), and you have to submit a significant payment with your offer.

Does this apply to other tax forms too? We're about to submit for the Restaurant Revitalization Fund and I'm worried about similar delays.

Absolutely! This consistency rule applies to pretty much all tax forms and federal relief programs. For the Restaurant Revitalization Fund specifically, make sure your business name matches exactly what's on your business license, EIN documentation, and tax returns. I've seen applications get stuck in processing because the business applied as "Joe's Pizza" but their tax returns show "Joseph's Pizza LLC." The systems are often matching these entries automatically, and even minor differences can kick it out for manual review, which means significant delays.

You don't need to have fully shut down to qualify. There are two main ways to be eligible: 1) Your business operations were fully/partially suspended due to government orders limiting commerce, travel, or group meetings due to COVID-19, OR 2) You experienced a significant decline in gross receipts during a calendar quarter compared to 2019 (specific percentage requirements depend on which quarter you're claiming). Reduced hours can definitely qualify under the first test if they were the result of government restrictions. Document everything showing how the restrictions affected your operations!

Thank you for explaining! We definitely had reduced capacity requirements from our county health department that forced us to operate at 50% for several months. I'll gather all the official orders and our schedule changes to document this properly. I appreciate the clear explanation - our accountant was being super cautious about this claim since the IRS has been scrutinizing them closely.

Do you meet with your CPA throughout the year or just at tax time? I'm wondering if there's value in quarterly check-ins or something.

I do both - a main consultation during tax prep season but also a mid-year check-in around June/July to make sure I'm on track with estimated payments and to discuss any new business developments or investments. The mid-year meeting is actually incredibly valuable because it gives me time to implement tax-saving strategies BEFORE year-end when many opportunities disappear. For example, last July we identified that I could purchase some needed business equipment before December and fully deduct it, saving me about $1,400 in taxes. Waiting until tax season in April would have been too late.

What kinds of deductions did you miss? I'm curious because I'm in a similar situation and wondering if I'm leaving money on the table.