I've had an ESPP for almost a decade now and the most important thing to understand is the difference between qualifying and disqualifying dispositions when you do eventually sell. To get preferential tax treatment (pay less), you typically need to hold the shares for AT LEAST 1 year after the purchase date AND 2 years after the offering date. If you sell earlier, it's a disqualifying disposition and you'll pay ordinary income tax rates on the gains. Just something to keep in mind as you continue to hold those shares.

Just to add another perspective - I've been in a similar ESPP situation with my company for about 2 years now. The advice here is spot-on about not needing to report anything until you sell. One thing that helped me was actually calling my company's benefits department directly. They were able to confirm exactly how they handle the discount reporting on my W-2 and gave me a copy of our specific plan document. Each company can handle ESPPs slightly differently, so getting the details from your HR/benefits team at Target might save you some guesswork. Also, if you log into your Fidelity account, there should be a section that shows your purchase history with all the details like purchase dates, shares bought, and the discount applied. That'll be super helpful when you eventually do sell and need to calculate your cost basis properly.

For what it's worth, I went through this exact same nightmare with TaxSlayer and my Fidelity 1099-B last year. Here's what finally worked for me: First, ignore TaxSlayer's direct import - it's broken and will cause more problems than it solves. Second, organize your 1099-B by the checkbox categories before you start entering anything. Group all your Box A transactions together, Box B together, etc. For the wash sales specifically, look for them in column (g) on your 1099-B. In TaxSlayer, when you're entering each transaction (or summary), there should be a field labeled something like "Adjustment for wash sale" or "Wash sale loss disallowed." That's where you enter the amount from column (g). The key insight that saved me hours: you can absolutely use summary reporting for most transactions. Don't let TaxSlayer's confusing interface trick you into thinking you need to enter every single trade. If the basis was reported to the IRS (Box D checked), just sum up all transactions of the same type and enter one summary line. One last tip - print out your completed Form 8949 from TaxSlayer and double-check it against your 1099-B totals. The software sometimes miscategorizes things, and you want to catch that before filing.

Reading through all these responses has been incredibly helpful! I've been struggling with this exact same issue using TaxSlayer and my E*TRADE 1099-B. Based on what everyone's shared, I think I've been overcomplicating this whole process. I was trying to enter every single transaction individually when I could have been using summary reporting for most of them. One thing I'm still confused about though - if I have wash sales that span across different reporting categories (some in Box A, some in Box B), do I need to allocate the wash sale adjustments proportionally to each summary entry? Or can I just put the total wash sale adjustment in one category? Also, for anyone who's used the copy feature in TaxSlayer that was mentioned - does it work when you're doing summary entries, or is that only useful when entering individual transactions? Thanks everyone for sharing your experiences. This community has been way more helpful than TaxSlayer's customer support!

Anyone know if FreeTaxUSA is good with Schedule C for self-employment? I'm a freelancer and TurboTax always upsells me to their expensive "self-employed" version. Wondering if FreeTaxUSA handles this better?

I've been using FreeTaxUSA for three years now and can confirm it's absolutely legitimate - they're an IRS-authorized e-file provider with excellent security. Regarding your state return concern, you're right to check carefully at checkout. FreeTaxUSA's federal filing is free, but state returns typically cost around $14.99 each. Here's what to look for: after completing your federal return, you should see an option to "Add State Return" before finalizing. Make sure both federal AND state show "e-file" status before paying. If your state only shows "print and mail," that means e-filing isn't available for your specific state through their system. I've never had any issues with refund timing compared to when I used more expensive services. The IRS processes returns the same regardless of which software you use to file. You'll save significant money compared to TurboTax while getting the same result!

There's one thing nobody mentioned yet - the tax basis of your business for eventual sale. Make sure you're tracking your adjusted basis correctly! Even though you didn't claim the amortization expense on Schedule C, if you reported it on Form 4562, your basis in the goodwill is still being reduced each year. When you sell, your gain calculation will use this reduced basis. If you don't fix this issue with amended returns/Form 3115, you could end up paying tax on a larger gain than you should - effectively getting taxed twice!

This is a really thorough discussion! I'm dealing with something similar but with equipment depreciation on my Schedule C business. Reading through all these responses, it sounds like the key is having that Form 4562 documentation to show the IRS that you were tracking the depreciation properly, even if it didn't make it to the expense line. One question I haven't seen addressed - when you file the amended returns for the open years, does the IRS typically process those refunds quickly? I'm worried about cash flow since we're talking about potentially significant refund amounts. Also, has anyone had experience with the IRS questioning why these deductions were missed in the first place during the refund process? The taxr.ai tool mentioned earlier sounds interesting for identifying these issues systematically. I'm wondering if anyone has used it specifically for equipment vs. intangible asset depreciation issues?

I'm a little confused by some of the responses. I own an S-Corp too and take both salary and distributions. Aren't S-Corp owners REQUIRED to take reasonable compensation as W-2 income? That's what my accountant always told me - that you can't just take K-1 distributions and no salary if you're actively working in the business.

I'm really sorry to hear about your husband's business struggles. Unfortunately, the other commenters are correct - since your husband only took K-1 distributions and wasn't on W-2 payroll, he likely won't qualify for traditional unemployment benefits in most states. However, don't give up hope! There are a few things worth exploring: 1. **State-specific programs**: Some states have created their own assistance programs for business owners. Contact your state's economic development office or small business administration office. 2. **SBA disaster loans**: If the business decline was related to economic conditions, you might qualify for an Economic Injury Disaster Loan (EIDL) if any programs are still available. 3. **Local assistance**: Many cities and counties have emergency assistance programs for residents facing financial hardship. Also, as others mentioned, your husband should have been taking reasonable compensation as W-2 wages according to IRS rules for active S-Corp owners. This is something to discuss with a tax professional - both for compliance going forward and to understand if there are any retroactive issues to address. I'd recommend contacting a local tax professional or small business development center (SBDC) for personalized guidance on both the unemployment question and proper S-Corp payroll structure moving forward.