Just wanted to add another perspective here - I work as a tax preparer and see wash sale confusion constantly during tax season. The key thing to remember is that wash sales don't increase your taxes, they just defer losses to future years. In your case with the $55,786.95 net gain, that's exactly what you'll report on Schedule D. The $373,152.71 in disallowed wash sale losses aren't "lost forever" - they've been added to the cost basis of your replacement shares. When you eventually sell those shares (without triggering another wash sale), you'll get to use those deferred losses. One tip: if you're an active trader, consider using specific identification for your lots rather than FIFO. This gives you more control over which shares you're selling and can help minimize unintended wash sales. You can usually change this setting in your brokerage account preferences. Your 1099-B is correct as presented - just use that net gain figure and you're good to go!

I went through a very similar situation last year with even larger wash sale amounts and completely panicked thinking I owed way more in taxes than expected. After reading through all the helpful responses here, I can confirm what everyone is saying is correct. The key insight that finally clicked for me was understanding that wash sales don't create additional taxable income - they just defer losses to future tax years. Your brokerage has already done all the complex math to arrive at that net gain figure of $55,786.95, which includes all the wash sale adjustments. One additional tip I learned the hard way: if you're planning to do any tax-loss harvesting near year-end, be very careful about the 30-day wash sale window extending into the new year. I accidentally triggered some wash sales in early January that affected my prior year's return, and I didn't realize it until I was already filing. Also, definitely keep detailed records of all your trades. The IRS explanations are confusing, but having a paper trail makes everything much clearer if you ever need to review the calculations or face an audit. Your $55,786.95 net gain is what you'll report on Schedule D - that's it!

You might want to look into whether you qualify as an independent contractor rather than an employee. Many PCAs are actually misclassified. If you're actually an independent contractor, you'd handle your own taxes through quarterly estimated payments anyway, and this might simplify things for you going forward. The IRS has a form called SS-8 that helps determine proper worker classification. Worth looking into since your intermediary is already failing at basic employer responsibilities!

I'm dealing with a similar situation right now and wanted to share what I've learned from calling the IRS directly. When your employer fails to withhold taxes despite proper W-4 submission, you can actually request what's called a "lock-in letter" from the IRS. This is a formal notice that the IRS sends to your employer specifying exactly how much must be withheld from your paychecks. To get this, call the IRS at 1-800-829-1040 and ask for the "employee protection" department. You'll need to provide documentation that you submitted proper W-4 forms and that your employer ignored them. The IRS takes this pretty seriously since employers are legally required to follow valid withholding instructions. Also, since you're working through DSS as a PCA, you might have additional protections under your state's labor laws. Many states have specific regulations about how fiscal intermediaries must handle payroll for state-funded positions. I'd recommend contacting your state's Department of Labor wage and hour division - they often have more teeth than just complaining to DSS directly. Keep fighting this! You shouldn't have to bear the burden of your employer's failure to follow basic tax laws.

Have you looked into making an S-corp election? I deliver for UberEats full time and switched to an S-corp structure last year. Saved me about $4500 in self-employment taxes. Basically you form an LLC, elect S-corp tax treatment, pay yourself a reasonable salary (which still gets regular employment taxes), but then you can take the rest as distributions which AREN'T subject to self-employment tax. There are some costs involved with setup and you need to run payroll, but if you're making $40k+ it's often worth it.

Hey Sophia! I totally get the panic - I was in your exact shoes two years ago making around $38k with delivery apps. The good news is it's not as scary as it seems once you understand the basics. Here's the real deal: You won't owe 30-40% to the IRS. That person was probably mixing up gross vs net income. As a gig worker, you'll pay self-employment tax (about 15.3%) plus regular income tax on your profits AFTER deductions. With proper deductions (especially mileage), your effective tax rate will likely be closer to 15-20%. Your mileage tracking in a notebook is perfect! That's going to be your biggest deduction. Also track things like: - Phone bill (business portion) - Insulated delivery bags - Car washes if you clean your car for work - Any other delivery-related expenses For the quarterly payments - yes, you should have been making them, but don't panic. The penalty isn't huge for first-time situations, especially if you file and pay on time. Going forward, set aside about 25% of your earnings each week for taxes. One last tip: consider getting help this year since it's your first time. Whether that's a tax pro, software designed for gig workers, or even calling the IRS directly for guidance. It's worth the investment to get it right and understand the process for next year. You've got this! The tax stuff seems overwhelming at first but becomes routine once you learn the system.

This is such a frustrating situation, but you're definitely not alone in dealing with this. As someone who's been through similar partnership disputes, I'd strongly recommend documenting everything right now - save all those unanswered emails and voicemails as proof of your good faith efforts. The extension route mentioned earlier is probably your safest bet given the timeline. Form 4868 buys you six months to sort this out properly, and the penalties for underpaying estimated taxes are usually much smaller than the penalties for not filing at all. One thing I'd add - if your fiancée has bank records showing any distributions or payments from the LLC during the tax year, those can help support whatever estimates she makes. The IRS understands that sometimes partners don't cooperate, but they want to see you made reasonable efforts to comply. Has she tried reaching out to any other business contacts who might know the LLC's accountant? Sometimes going through a mutual connection can break the ice when direct communication isn't working.

This situation is unfortunately more common than you'd think, especially with dissolved partnerships. Your fiancée absolutely should not ignore this - the IRS will expect her to report her share of partnership income regardless of whether she receives the K-1. Here's what I'd recommend based on similar cases I've seen: 1. **File an extension immediately** - Form 4868 gives you until October 15th, but remember any taxes owed are still due April 18th. Estimate conservatively based on prior years. 2. **Create a paper trail** - Send one final certified mail request to both the ex-spouse and the LLC's registered address demanding the K-1. Reference her ownership rights and legal obligation to file taxes. Keep the receipt. 3. **Gather supporting documents** - Previous K-1s, operating agreement, bank statements showing distributions, any correspondence about the business. This establishes her ownership percentage and income pattern. 4. **Consider legal consultation** - A business attorney can send a formal demand letter which often gets faster results than personal requests. Many offer free consultations for straightforward cases like this. The key is showing the IRS she made good faith efforts to obtain required documents. Don't let her ex-spouse's non-cooperation derail her tax compliance - there are ways to handle this properly even without their cooperation.

Make sure you don't just throw these away! The IRS computers will think the estate still owes estimated payments and will start generating automated penalty notices if you ignore them. Happened to my neighbor and it took him almost a year to resolve the mess.

I went through this exact same situation with my mother's estate about two years ago. The IRS kept sending Form 1041-ES vouchers even though we had properly closed the estate in 2020. What worked for me was sending a certified letter to the IRS with copies of the final Form 1041 (clearly marked "Final Return"), the court order closing the estate, and a brief explanation that the estate had been fully distributed and closed. I included the estate's EIN and my contact information as executor. The key thing is to act quickly - don't let these sit around. The IRS automated system will start generating penalty notices if it thinks estimated payments are being missed. It took about 6-8 weeks after I sent the documentation, but I eventually received a letter confirming they had updated their records and would stop sending the vouchers. Keep copies of everything you send and use certified mail with return receipt so you have proof they received it. This is definitely fixable, just needs the right paperwork to get their system updated.