I just went through this whole wash sale nightmare last week. One thing nobody mentioned is that some brokers report wash sales differently on their 1099-B forms. For example, my Schwab statement clearly marked the wash sale adjustment with code "W" and a separate column, but my E*TRADE statement had it buried in the footnotes!

Great point about the different brokerage formats! I've dealt with statements from several brokers and they all seem to handle wash sale reporting differently. Here's what I've learned: **Fidelity**: Look for Box 1g on the 1099-B - they clearly mark wash sale adjustments with a "W" code and show the disallowed loss amount. **Vanguard**: They include wash sale info in Box 1f (adjustment code) and provide detailed explanations in the supplemental information section. **Charles Schwab**: As you mentioned, they use code "W" and have a separate column for wash sale adjustments - probably the clearest format. **Robinhood**: This one's tricky - they often combine multiple transactions and the wash sale adjustments can be hard to track. Look for the "Wash Sale Loss Disallowed" line item. **E*TRADE**: Like you said, often buried in footnotes or shown as an adjustment to cost basis without clear labeling. The key is to look for any codes like "W" or "D" (for disallowed loss) and check both the main form and any supplemental statements. When in doubt, most brokers have customer service that can walk you through reading their specific 1099-B format. Don't feel bad about calling - these forms are genuinely confusing even for experienced investors!

I'm confused about something - do I need to set up a separate user account on my laptop for business vs personal use to prove the percentage? Or is that overkill?

One thing I haven't seen mentioned yet is that you should also keep receipts and documentation for the actual purchase of your laptop and monitor. The IRS will want to see proof of the cost basis for your deduction calculations. Also, since you're transitioning from using a work laptop to purchasing your own, make sure you can clearly show when you started using your personal equipment for business purposes. This becomes important for the depreciation timeline if you go that route instead of Section 179. I'd recommend taking photos of your setup and keeping a simple log of when you first started using it for your 1099 work. Having that paper trail makes everything much smoother if you ever get audited.

This sounds incredibly frustrating! I haven't dealt with Jackson Hewitt specifically, but I went through something similar with TurboTax's refund advance program a couple years ago. What finally worked for me was being very persistent about getting the exact mailing address and account information for direct repayment. Have you tried asking the customer service reps to email you the written repayment instructions? Sometimes they have different information available via email that they don't mention over the phone. Also, if you paid for the advance with a debit/credit card originally, you might be able to reference that transaction to help them locate your account in their system. Document everything in case you need to dispute any potential credit reporting issues later!

I actually went through this nightmare with Jackson Hewitt two years ago and it was absolutely maddening! What finally worked for me was bypassing JH entirely and going straight to MetaBank (which handles most of their advances). I found MetaBank's direct customer service line and explained the situation - they were able to locate my advance account using my SSN and the advance amount. They provided me with specific wire transfer instructions and a mailing address for check payments. The key was having my original advance agreement handy when I called them. JH's customer service seems completely disconnected from the actual repayment process, which makes no sense but explains why you're getting the runaround. Try calling MetaBank directly at their customer service line - they should be able to help you bypass JH's useless phone maze entirely.

Anna, I'm so sorry to hear about your diagnosis - dealing with a critical illness is incredibly stressful without having to worry about tax implications on top of everything else. From reading through all the excellent advice here, it sounds like you have a clear path forward: get that written confirmation from HR about whether your premiums were pre-tax or after-tax, and then you'll know exactly where you stand. One thing I wanted to add that I haven't seen mentioned is that if you do end up owing taxes on this payout, you might want to consider setting aside a portion of the $13,500 right now in a separate savings account for taxes. That way you won't accidentally spend money you might owe to the IRS, and if it turns out the benefits are tax-free, you'll have a nice emergency fund. Also, since you mentioned this is causing you stress during an already difficult time - many hospitals and treatment centers have financial counselors who are familiar with insurance payouts and their tax implications. They might be another resource to consider if you need additional guidance beyond what HR can provide. Take things one step at a time, focus on your recovery, and know that this tax situation is definitely manageable with the right information. Wishing you all the best with your health journey!

Anna, I'm so sorry to hear about your diagnosis. Having been through a similar situation with my own critical illness payout, I completely understand how overwhelming it can feel to deal with tax questions on top of everything else you're going through. The advice everyone has given here is excellent, especially about checking with HR to determine if your premiums were pre-tax or after-tax. But I wanted to add one more thing that really helped me: if you do need to make estimated tax payments, consider making them quarterly going forward rather than one lump sum, even if this payout is a one-time thing. The reason is that if you have ongoing medical expenses or other changes to your income due to your health situation, making quarterly payments gives you more flexibility to adjust as you go. You can always increase or decrease future payments based on how your situation evolves. Also, don't forget to ask your tax preparer (or research yourself) about any additional medical expense deductions you might be eligible for beyond just the basic threshold everyone mentioned. Sometimes there are specific provisions for critical illness situations that can help offset taxable income. Take care of yourself first - everything else is just paperwork that can be figured out. Sending positive thoughts for your recovery!

Am I the only one who withdraws from my HSA without actually submitting receipts? I've been saving all my medical receipts for years (have about $3,400 worth) but haven't taken any distributions yet because I'm treating my HSA like another retirement account. I've heard you can reimburse yourself years later as long as the HSA was established before you incurred the medical expense. Is that right?

This is such a helpful thread! I'm dealing with the same situation - got my 1099-SA with code 1 and was worried I did something wrong. Reading through everyone's experiences, it sounds like I'm on the right track. One thing I want to add for anyone else reading this: make sure you double-check that ALL your HSA distributions were actually for qualified medical expenses. I almost made a mistake because I used my HSA debit card at CVS and assumed everything was qualified, but it turns out I bought some regular vitamins and sunscreen that don't count as qualified medical expenses under IRS rules. Also, @Isla Fischer, that strategy of saving receipts and reimbursing yourself later is brilliant! I never thought about using my HSA as a retirement account like that. Definitely something to consider for future medical expenses. Thanks everyone for sharing your experiences - this community is so much more helpful than trying to navigate the IRS website alone!