Anyone know if Cash App's tax documents are usually accurate? Last year I had issues with Robinhood where their 1099 had some incorrect cost basis info and it created a huge headache.

Great question about Cash App's tax document accuracy! I've been using Cash App for trading for about 2 years now and generally find their 1099-B forms to be reliable, but like Diego mentioned, it's always worth double-checking. One thing I learned the hard way - make sure to keep your own records throughout the year rather than relying solely on their year-end documents. I use a simple spreadsheet to track each trade with the date, symbol, shares, buy/sell price, and any fees. This makes it much easier to spot any discrepancies when the 1099-B arrives. Also, if you do find errors on your 1099-B, Cash App's customer support can usually provide corrected forms, but it can take a few weeks during tax season. So the earlier you review your documents, the better! The wash sale tracking seems to be where most platforms struggle, so that's definitely worth paying extra attention to if you've done any frequent trading in the same stocks.

Warning about the red ink forms - order them NOW from the IRS if you're going that route! I waited until January last year and they were completely out of stock. Ended up having to buy them at an office supply store for like $50 which was highway robbery but I was desperate. The IRS sends them for free but they run out every year during tax season.

I went through this exact same confusion last year! Here's what worked for me after making some mistakes: First, yes you absolutely need Form 1096 - it's like a cover sheet that tells the IRS "hey, I'm sending you these 1099 forms." You attach it to Copy A of your 1099-NEC when mailing to the IRS. For the red ink issue - if you're only dealing with one or two forms, honestly just order the official ones from the IRS website (they're free but take 7-10 days). If you need them faster, most FedEx Office locations carry the official red ink versions for about $3-4 per form. BUT here's what I wish someone had told me earlier: since you're dealing with attorney fees on a 1099-NEC, double-check that you actually owe more than $600 to this lawyer in the tax year. If it's under $600, you don't need to file the 1099-NEC at all (though you can still deduct the expense on your business taxes). Also, make sure you have the lawyer's correct TIN/SSN on the form - the IRS gets really cranky about mismatched taxpayer identification numbers. I learned that one the hard way! The electronic filing through FIRE is honestly easier once you get past the initial setup, but for just one form, paper might be simpler for a first-timer.

The most important thing I learned from my tax debt situation is DONT IGNORE IT!! I buried my head in the sand for 2 years and my original $15k debt ballooned to over $28k with penalties and interest. For real tho, call the IRS yourself first. The people on the phone are actually pretty helpful if you're honest and polite. At minimum, get on a basic payment plan to stop the penalties from getting worse while you figure out your options.

I'm dealing with a similar situation - about $19,000 in back taxes from a consulting business that went under in 2022. The constant mail from the IRS was giving me panic attacks, but I finally called them directly last week using the number Isabella mentioned (1-800-829-1040). The IRS agent was actually really understanding and explained that I could set up an installment agreement for around $320/month based on my current income. She also mentioned that once I get current on payments, I might qualify for penalty abatement which could reduce the total amount. What really helped was having all my financial documents ready before calling - bank statements, pay stubs, and a list of monthly expenses. The whole process took about 45 minutes and I walked away with a manageable payment plan instead of the crushing anxiety I'd been carrying for months. Emma, definitely try calling them directly first before paying thousands to a tax relief company. The worst they can say is no, but in most cases they'd rather work with you than go through the collection process.

I think a lot of people are missing that there's a difference between the penalty for late FILING and late PAYMENT. Since you're a nonprofit that doesn't owe taxes, you're only dealing with the late filing penalty, which might give you more flexibility. Also worth checking if you qualify for first-time penalty abatement (FTA) which the IRS offers for organizations with a clean compliance history. You don't even need reasonable cause for that - just a clean record for the past 3 years.

Actually, @Jake Sinclair raises an important question about FTA for nonprofits. From my understanding, first-time penalty abatement is primarily available for income tax penalties, employment tax penalties, and certain excise tax penalties - but NOT for information return penalties like the Form 990 late filing penalty. The IRS treats information return penalties (which is what Form 990 falls under) differently from tax penalties. For Form 990 late filing, you really need to establish reasonable cause rather than relying on FTA provisions. That said, your situation does have some strong elements for reasonable cause: volunteer status, small organization with limited resources, and a significant life event (new baby). I'd focus your letter on those factors rather than trying to pursue FTA, which likely won't apply to your Form 990 situation.

just wanna add that your parents should probably claim you as a dependent if they provide more than half your support (housing, food, tuition help, etc). the american opportunity credit is worth up to $2500 and your parents can only claim it if they claim you as a dependent. since you only worked one month, you probably dont have enough income for the credit to be worth much to you personally. you'll probably still get a small refund from your summer job withholding regardless of whether youre a dependent or not. make sure to file regardless!

One thing nobody's mentioned that tripped me up last year - if u make under like $12,500 (the standard deduction amount) filing as single, you might not even need to file federally! But u should STILL file to get any withheld money back from those summer paychecks. For the 1098-Ts, whoever claims you as dependent gets to use those for the education credits. in my case, my parents let me file independent last year because they make too much to qualify for the education credits anyway (there's an income limit). but if ur parents can use the credits, usually best for them to claim you and you can still file to get ur withholding back on ur own return.