Shoot I didn't even think about the dependent thing! I'll definitely ask my parents. What kind of records should I keep exactly? I don't think Cashapp gives very detailed descriptions for each payment.

For record-keeping, you should save monthly statements from Cashapp as a start. But you're right that Cashapp descriptions are often vague or just have emojis. I recommend creating a simple spreadsheet where you note each incoming payment that was income (like your moving help) versus what was reimbursement. Even just a basic note for each transaction like "Mike paying me back for concert tickets" vs "Payment for helping move furniture" helps a lot. Take screenshots of conversations if people were paying you through Cashapp for services. The better your documentation, the easier it would be if there were ever questions.

Starting this year, payment apps are supposed to send 1099-K forms if you received over $600 in transactions, but I heard they delayed implementing that fully. For 2024 taxes (filed in 2025), you'll probably get a form if you crossed that threshold.

What if some of my HSA contributions were made directly by me (not through payroll)? I contributed $3,000 through my employer and then added another $2,000 on my own to max out the individual limit.

For contributions you made directly (not through payroll), those should definitely show up in the tax breaks section. In TurboTax, those direct contributions should be entered in the HSA section specifically, not as part of your W-2 entry. Those contributions will appear on Form 8889 Line 2 as "contributions made to your HSA" and will become an above-the-line deduction on your Form 1040 Schedule 1. This reduces your adjusted gross income directly. You should see these contributions reflected in your tax breaks section because they're giving you an additional deduction beyond what was already excluded from your W-2 wages.

Hmm, that's a good point - I need to check if I accidentally entered them twice. I know for sure I entered them during the W-2 section, but I can't remember if I also entered them again in the HSA section. I'll go back and review. Thanks for the tip!

What about the "Covered/Uncovered" designation on the Stash form? Mine has both types of transactions and I'm not sure if that affects how I enter them.

The "Covered/Uncovered" designation is directly related to whether the cost basis was reported to the IRS. "Covered" securities (typically those purchased after 2011) have their cost basis reported to the IRS by Stash, and these usually correspond to the Code D transactions I mentioned. "Uncovered" securities don't have their cost basis reported to the IRS by the broker, so you're responsible for calculating and reporting the correct cost basis yourself. For these, you'll need to enter the purchase information manually and keep good records in case of an audit. TurboTax has separate entry sections for covered and uncovered securities, so make sure you're entering each transaction in the correct section.

Foreign tax paid usually goes in the Foreign Tax Credit section, not directly on the 1099-B entry screens. In TurboTax, after you finish entering all your 1099-B info, look for a section about foreign taxes or foreign tax credit. Even small amounts should be entered because they're directly creditable against your tax bill.

The transcript trick is legit. Go to irs.gov and search for "Get Transcript Online." You'll need to create an account if you don't have one (they verify your identity with credit report info). Look for the Account Transcript for 2024 once you're in. Check for codes like 846 (refund issued) or 570/971 (hold/notice).

Nope, I'm not claiming either of those. Just a standard return with W-2 income. Thanks for the suggestion though! I'm just going to be patient based on what everyone is saying. Seems like this is pretty normal even though it's frustrating.

Thanks for the suggestion about adjusting my withholding going forward. Do you know how I would calculate how much extra to withhold to make up for this year's shortfall? And you're right about the state taxes - I need to check those too. I was so shocked by the federal issue that I didn't even think about that.

You can use the IRS Tax Withholding Estimator on their website - it lets you input how much has been withheld so far and will calculate what you need for the remaining paychecks. Just select that you want a bigger refund and it'll tell you what number to put on your W-4. For your state taxes, each state has different rules, but if they weren't withholding federal, there's a good chance they missed state too, especially if you're in a state that bases its withholding on the federal W-4 form.

This is a really good point! OP needs to check their employment status. My neighbor thought she was a regular employee but her company had her classified as a 1099 contractor (incorrectly) and wasn't withholding anything. Led to a huge tax bill and she had to file an SS-8 form with the IRS to get it sorted out.