Make sure you're keeping track of the adjusted basis for any replacement shares! The wash sale rule disallows the loss, but that loss doesn't disappear forever - it gets added to the basis of your replacement shares. This matters for when you eventually sell those replacement shares.

I'm dealing with a similar wash sale situation as a non-resident, and this thread has been incredibly helpful! One thing I wanted to add based on my experience is that you should double-check your 1099-B carefully because some brokerages don't always correctly identify ALL wash sales, especially if you have accounts at multiple brokerages. I discovered that I had wash sales that weren't marked on my 1099-B because I sold shares at one brokerage and bought similar shares at another brokerage within the 30-day window. The wash sale rule still applies in this situation, but the brokerages don't communicate with each other to identify these cross-brokerage wash sales. So even if your 1099-B shows some wash sales, make sure to review all your transactions across all accounts to catch any that might have been missed. You'll still need to report these on Form 8949 with code "W" even if they weren't identified by your brokerage.

Has anyone noticed that TaxSlayer's prices went up again this year? I've used them for the past 3 tax seasons and I swear the same service tier cost $15 less last year. And now they're pushing this File&Go thing which is basically just them charging extra to take their money later instead of now. I'm thinking about switching to a different service next year. Anyone have recommendations for something more straightforward with fewer upsells and hidden fees?

I went through this exact same confusion with TaxSlayer last week! The File & Go option is definitely just a payment method - you're not missing out on any actual tax benefits by skipping it. What helped me decide was realizing that if I have $39 to pay TaxSlayer now, I'd rather keep that money in my refund instead of giving it to them as an extra convenience fee. The "tax preparation fees" they mention are just TaxSlayer's own software fees, not anything the IRS requires. I ended up paying directly with my debit card and saved the extra charges. My taxes were filed just fine without File & Go. Don't let their wording make you think it's mandatory - it's purely optional and costs more than paying upfront.

I'm confused about something - if the employer took the money pre-tax but then only reported half of it as Cafe 125, wouldn't that mean her W-2 wages are wrong? Like they reduced her pay by the full amount but only gave her tax benefit for half?

This is a frustrating situation that unfortunately happens more often than it should. Based on what you've described, there are really two separate issues here that need to be addressed: 1. **The W-2 reporting**: If your sister-in-law's paystubs show the full double amount was deducted pre-tax, but her W-2 only shows half in the Cafe 125 box, then her taxable wages are likely incorrect. She's essentially being taxed on money she never actually received. 2. **The refund**: The employer owes her a refund for the excess premiums they incorrectly withheld. Since it's already February and they've been unresponsive since October, I'd suggest a multi-pronged approach: - Document everything: Keep copies of all paystubs, communications with HR, and the current W-2 - File her taxes based on the W-2 she received (the IRS matches returns to W-2s) - Continue pursuing the employer for both the refund AND a corrected W-2 if needed - Consider escalating within the company (beyond HR to senior management) - If they remain unresponsive, file a wage complaint with your state's Department of Labor The key thing to remember is that this isn't really a tax deduction issue - it's an employer payroll error that needs correction at the source.

Has anyone tried using the simplified home office deduction ($5 per square foot up to 300 sq ft) vs itemizing all home expenses? I'm trying to figure out which would be better for my clothing reselling business... I use about 150 sq ft for inventory storage and photography.

For your situation with $11,500 in sales and $6,700 in expenses, you're definitely on the right track with Schedule C as a sole proprietor. That puts you at about $4,800 in profit, which means you'll owe self-employment tax on that amount (about $679). A few specific tips for clothing resellers: - You can absolutely keep purchasing receipts together rather than matching each item individually. The IRS cares about your total Cost of Goods Sold, not item-by-item tracking. - Don't forget to deduct platform fees (eBay, Poshmark, etc.), shipping supplies, storage containers, and even a portion of your internet bill if you use it for business. - Consider opening a separate business checking account - it makes tracking so much easier and looks more professional if you ever get audited. At your current profit level, sole proprietorship is definitely the most cost-effective structure. The extra complexity and costs of an LLC or S-corp wouldn't be worth it until you're making significantly more profit. Keep good records and you'll be fine!

Dont forget you might also need to file estimated quarterly taxes throughout the year depending on how much youre making. The IRS expects you to pay taxes as you earn income, not just once a year. Since you dont have an employer withholding taxes from your paychecks, you gotta do it yourself. I learned this the hard way and got hit with penalties my first year of self-employment :

Quick tip - make sure your tax software is calculating your Qualified Business Income Deduction (Section 199A). This is a deduction that lets self-employed people deduct up to 20% of their business income in addition to regular business expenses. Some free tax software might not include this automatically.