Not to muddy the waters, but have you considered the possibility that this might be Section 1231 property? If so, neither Schedule D nor reporting it as ordinary income on the front of the return may be correct - Form 4797 might still be relevant but for different reasons.

Based on all the discussion here, I think you're on the right track with Schedule D treatment, but I'd strongly recommend getting this reviewed by someone with deep S-Corp expertise before filing. The short holding period (10 days) is really the biggest red flag that could invite IRS scrutiny. One thing I haven't seen mentioned - make sure you're also considering the impact on your client's QBI deduction. If this gain ends up being treated as ordinary business income rather than capital gains, it could affect their Section 199A calculation. The characterization of this transaction could have ripple effects beyond just the immediate tax on the gain. Also, given that this is a $135K gain, the stakes are high enough that it might be worth investing in a private letter ruling if your client is concerned about audit risk. It's expensive but would give you definitive guidance for this specific situation.

Ugh I got audited last year and this exact issue came up. My advice is to take photos of ALL receipts where you claimed business expenses and store them digitally by date. I had to go through hundreds of receipts during my audit and the ones I couldn't find or that were too faded to read were automatically disallowed as deductions.

Great thread! I'm dealing with this exact same situation with my freelance graphic design work. One thing I learned from my accountant is that you should also keep a simple business expense log alongside your receipts. Just a spreadsheet with columns for date, vendor, total amount, business portion, and business purpose. This way if you ever get audited, you're not just relying on highlighted receipts - you have a clear paper trail showing your thought process for each deduction. The IRS loves documentation that shows you were being deliberate and organized rather than just guessing. Also, don't forget that you can deduct the business portion of things like gas when you're making those mixed shopping trips! If you drove to Target specifically to buy business supplies but also grabbed personal items while there, you can still claim the mileage as a business expense.

Has anyone tried H&R Block's free version? I thought they handled HSAs in their free tier but maybe that changed this year?

I went through this exact same frustration last year! TurboTax's HSA upsell is so misleading - they hook you with "free" filing then spring the upgrade requirement on you halfway through. For what it's worth, I ended up using FreeTaxUSA and was really happy with it. The HSA forms (Form 8889) were handled seamlessly in their free federal version, and I only paid the $15 for state filing. The interface isn't as polished as TurboTax but it gets the job done without any surprise fees. One tip: make sure you have your HSA year-end statement handy before you start. It shows your total contributions, employer contributions, and any distributions you made. That's really all you need for the HSA portion, and it should only add maybe 10 minutes to your filing time. Don't let these companies convince you that having an HSA makes your taxes "complex" - it's literally just one additional form!

I went through this exact situation last year and understand your frustration! Your instincts are correct - Box 12W should only show HSA contributions, not healthcare premiums. The $6,000 amount appears to be incorrectly combining your $4,350 HSA contributions with your $1,650 premium payments. Here's what worked for me: I printed out the IRS Instructions for Forms W-2 and W-3 (specifically the section on Code W) and highlighted where it states that Code W is only for "employer contributions to health savings accounts." I also referenced IRS Publication 969, which clearly separates HSA contributions from health insurance premiums. When I presented this documentation to my HR department, I framed it as a compliance issue that could affect multiple employees, not just my personal tax situation. I mentioned that incorrect W-2 reporting could expose the company to potential liability if the IRS questions their payroll tax practices during an audit. In the meantime, you can absolutely file your taxes correctly using Form 8889 - just report your actual $4,350 contribution amount on the form regardless of what Box 12W shows. The HSA section of your tax software should handle this properly. Keep all your HSA provider statements as documentation. Don't let this stress you out too much - the IRS uses Form 8889 to determine actual over-contributions, not just the W-2 amounts. But getting it corrected is definitely worth the effort for future peace of mind!

I'm dealing with something very similar right now! My Box 12W shows $5,200 but my actual HSA contributions were only $3,800. Like you, my employer is being stubborn about fixing it, claiming their payroll system is correct. What's been most helpful for me is getting my HSA provider's year-end contribution summary - it clearly shows exactly what I contributed versus what my employer reported. I'm planning to use this as documentation when I file Form 8889. One thing I learned from calling the IRS (after waiting on hold for literally 3 hours) is that they specifically look at Form 8889 for HSA compliance, not just the W-2 amounts. The agent told me that as long as I report my actual contributions correctly on Form 8889, I shouldn't have issues with over-contribution penalties. Still frustrating that employers can't get this basic reporting right though! Especially when it's a compliance issue that could affect multiple employees. I'm considering escalating to our finance department next week with the IRS documentation others have mentioned here.

This whole thread has been super helpful! I'm dealing with a similar situation where I need to figure out my education credit history. One thing I learned from reading everyone's responses is that you might also want to check if your parents have copies of their actual tax software files (like TurboTax or H&R Block files) from those years. When my sister was trying to figure this out, she found that the tax software often has a summary page that clearly states which credits were claimed and the amounts, which can be easier to understand than trying to decipher the actual IRS forms. Plus, if your parents used the same tax preparer for multiple years, that person should have records and could probably answer your question in 5 minutes. It's frustrating how confusing these forms can be when the answer should be straightforward! Hope you get it sorted out soon.

I went through this exact same confusion last year! The key thing to understand is that line 23 on Form 8863 is asking about PRIOR tax years, not the current one. So when it says "No" for 2019-2022, it means that as of each of those years, you hadn't yet used up your 4-year lifetime limit from previous years. Since you mentioned there are numbers on line 29 of the 1040 and lines 7/8 of Form 8863 for all those years, your parents definitely claimed education credits. To confirm it was specifically the American Opportunity Credit (and not the Lifetime Learning Credit), check Part I of Form 8863 - if there are numbers in lines 1-8, that's the AOC section. So yes, it sounds like your parents did claim the American Opportunity Credit for you from 2019-2023, which would use up your full 4-year eligibility. The "No" checkboxes were just confirming you still had eligibility remaining at the time each return was filed. Hope this helps clear up the confusion!