Has anyone else noticed that H&R Block's help section is absolutely useless for these specific issues? I spent like an hour going through their FAQs and couldn't find any clear answer about multiple Box 19 entries.

I just went through this exact same issue with my W-2 showing two local tax amounts in Box 19! After reading through all these helpful comments, I was able to find the solution in H&R Block. For anyone still struggling: the key is that you MUST complete the federal section first before the local tax options become fully available. Once you move to the state section and start entering your state info, the local tax area will appear. After you enter the first locality and amount, scroll down - there's a small gray "Add another local tax" button that becomes visible. It's really easy to miss because it blends in with the background. Don't make the mistake I almost made of just adding the two amounts together. Each locality needs to be entered separately so you get proper credit on your local tax returns. Thanks to everyone who shared their experiences here - saved me hours of frustration!

5 Something nobody mentioned yet - check if your parents are claiming you as a dependent on their taxes! This is super important. If they are, you need to check a box on your return indicating this. It affects which tax credits you can claim. When I was 20 and filed my first return from my coffee shop job, I messed this up and both my parents and I claimed me, which caused a huge headache with the IRS sending letters later.

16 Don't forget about state taxes too! Your W-2 might have state tax info on it, and depending on where you live, you might need to file a state return in addition to federal. Some states don't have income tax tho.

Check if the 1099B is for a "surrender" or "lapse" of a life insurance policy. MetLife often issues these when a policy terminates with some cash value. The taxable amount is usually the surrender value minus premiums paid over the life of the policy. The form should indicate if they reported your basis to the IRS.

Hey Paolo! I went through something very similar with a MetLife 1099-B a couple years ago. The key thing to remember is that you absolutely need to report it even if you don't remember the investment - the IRS gets a copy of every 1099-B issued, so they'll be expecting to see it on your return. First, look at Box 3 on your form - if it's checked, that means MetLife already reported your cost basis (what you originally paid) to the IRS, which makes things easier. If it's not checked, you'll need to figure out your basis yourself or report the entire proceeds as gain if you can't determine it. Most likely this is from either: 1) An old employer life insurance policy with a cash value component that was surrendered, 2) A variable annuity or investment product you may have forgotten about, or 3) Stock you owned that was involved in a corporate action like a merger. I'd recommend calling MetLife's tax department to get clarification on exactly what transaction this relates to - they should be able to provide details about when the investment was established and what triggered the taxable event. Once you understand what it's for, entering it in your tax software is pretty straightforward in the investment income section. Don't stress too much - this is more common than you think and the tax software will walk you through it step by step!

Wondering if anyone knows how this would affect future W-2 employment? If the friend doesn't file for the sole proprietorship but then starts filing normally with their new W-2 job next year, will that trigger the IRS to look backward?

Your "friend" really needs to file that return, even if it's messy. I work in tax prep and see this situation all the time - the fear of filing an imperfect return often makes people avoid it entirely, which always makes things worse. Here's what I tell clients in similar situations: the IRS would rather see an honest attempt at filing with some organizational issues than no filing at all. They have programs specifically for first-time business owners who made mistakes. A few practical steps your friend can take right now: 1. Gather ALL bank statements for the business account (or personal account if mixed) 2. Make a simple spreadsheet listing income and expenses by month 3. Don't worry about perfect categorization - basic business expenses vs personal is enough to start 4. File for an extension if needed to buy more time to organize The penalties for not filing are harsh, but there are often penalty abatement options for first-time filers who can show reasonable cause. The key is showing good faith effort to comply, which means filing something rather than nothing. Also, closing the business license doesn't erase the tax obligation for the year it operated. The IRS will still expect to see that Schedule C on the 2022 return.

Just a heads up that your state might have different rules about deductions for children and families. I live in California and learned that some states have additional credits or deductions for new parents that aren't available federally. Might be worth checking your state's tax department website to see if there's anything specific you should be documenting.

Speaking as someone who just went through this first last year - one thing nobody mentioned is that if you had a FSA (Flexible Spending Account) or HSA (Health Savings Account) through your work for healthcare, you DEFINITELY want to keep all those medical receipts for the birth and prenatal care! You can use those accounts to pay for qualified medical expenses tax-free. The midwife, ultrasounds, and birth costs would all qualify for FSA/HSA reimbursement. The baby shower and registry items wouldn't, though.