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This thread has been incredibly helpful! I'm dealing with a similar situation but have an additional complication - some of my stock transactions involved ESPP (Employee Stock Purchase Plan) shares with different basis calculations. For anyone else in this boat, make sure you're using the correct cost basis for ESPP shares. The basis includes both the discounted purchase price AND any compensation income that was already reported on your W-2. I almost made the mistake of using just the purchase price, which would have resulted in double taxation on the discount portion. Also, if you have any foreign tax credits from international funds or ADRs, don't forget Form 1116. I learned this the hard way when I missed claiming credits for taxes paid to foreign governments on my international index funds. Every little bit helps when you're dealing with capital gains!

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Axel Bourke

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This is such an important point about ESPP shares! I made a similar mistake a couple years ago and ended up overpaying on my taxes because I didn't realize the discount was already included in my W-2 income. Quick tip for anyone with ESPP shares - your broker should provide a supplemental statement showing the correct cost basis that accounts for the compensation income. If they don't, you can usually find this information in your employee stock plan portal or HR system. It's worth the extra time to get this right because the IRS will definitely notice if your cost basis is wrong and you're double-reporting that discount income. Thanks for bringing up Form 1116 too - I had no idea about foreign tax credits on international funds until my CPA mentioned it. Even small amounts can add up over the years!

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Just wanted to add another perspective on this Form 8949 situation. I'm a tax preparer and see this confusion every single year during tax season! One thing that might help is to think of Form 8949 as creating separate "buckets" for your transactions. Each checkbox (A through F) represents a different combination of holding period (short vs long term) and whether the basis was reported to the IRS or not. You absolutely cannot mix different types of transactions on the same form. A few additional tips: - If you're missing cost basis information, check your old brokerage statements or contact your broker's tax department. They often have historical data going back several years. - For inherited stock, remember that you get a "stepped-up basis" equal to the fair market value on the date of death (or alternate valuation date). Don't use the original purchase price the deceased person paid. - Keep copies of everything! The IRS can ask for supporting documentation years later, especially if you have large capital gains or losses. The key is being methodical and not rushing through it. Better to spend extra time getting it right than dealing with IRS correspondence later.

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Anna Stewart

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Thank you so much for this professional insight! As someone who's been struggling with this exact issue, the "buckets" analogy really helps clarify things. I have a follow-up question about inherited stock - if I inherited shares that were purchased over multiple years at different prices, do I use the stepped-up basis for all of them based on the date of death value, or do I need to track the original purchase dates somehow? I'm worried about making an error since this involves a fairly substantial amount.

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Sean O'Brien

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I had the same issue with MI last month! Turned out my return was still in "processing" status even though it had been weeks. The state website doesn't update until it's fully processed, unlike the federal system. You might want to try calling their automated line at 517-636-4486 - sometimes it gives you more info than the website does. Hang in there, it's frustrating but normal this year!

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That automated line tip is gold! Just tried it and actually got more info than the website. Still says processing but at least I know they have my return. Thanks for sharing that number!

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Michigan resident here who went through this exact same thing last year! The "no match found" error is super common when their system is backlogged. I ended up waiting about 5-6 weeks before my return showed up in their lookup tool. One thing that helped me was keeping a screenshot of my submission confirmation from when I e-filed - that way you have proof you submitted it on time. Also, if you're really worried, you can request a payment trace after 6 weeks if your refund still hasn't shown up. Don't stress too much, MI is just notoriously slow compared to federal!

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Another commission earner here! Don't forget that you can also do estimated tax payments directly to the IRS if your withholding is too high on big commission checks. I've found it easier to have less withheld throughout the year and then make quarterly estimated payments based on my actual earnings. Gives me more control over my cash flow.

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Do you need to set that up with your employer or is it something you do on your own? Im new to the commission world and trying to figure all this out.

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Diego Flores

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Estimated tax payments are something you handle directly with the IRS - no need to involve your employer at all! You can make quarterly payments online through EFTPS (Electronic Federal Tax Payment System) or by mailing in Form 1040ES with a check. The key is calculating how much to pay each quarter. Generally you want to pay 25% of either 90% of your current year tax liability or 100% of last year's tax (110% if your prior year AGI was over $150k). Since commission income can be unpredictable, I usually base my estimates on last year's tax to stay safe. You can adjust your W-4 to have less withheld from your regular paychecks, then make up the difference with quarterly payments. Just make sure you don't underwithhold by more than $1,000 or you could face penalties. The IRS has worksheets in Form 1040ES that walk you through the calculations.

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Nia Jackson

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This is such a common frustration for commission earners! What you experienced is totally normal - the payroll system essentially projects your annual income based on that single large paycheck and withholds at the corresponding tax bracket. So when you made $14,000 in one week, the system calculated as if you'd make $728,000 annually ($14,000 Ɨ 52 weeks) and withheld at that higher bracket. The good news is this is just withholding, not your actual tax rate. When you file your return, your tax will be calculated on your actual total annual income. If you're overwithholding (which is likely), you'll get a refund. A few options to consider: You could adjust your W-4 to reduce withholding on regular paychecks, use estimated quarterly payments instead of relying solely on withholding, or work with payroll to see if they can process large commissions separately using the flat supplemental rate (which is currently 22% for most people). Many of the tools and strategies mentioned in the other comments could really help you optimize this!

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Ella Cofer

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I've been in the ticket reselling business for about 4 years now, and I can definitely confirm that expired/unsold tickets are legitimate inventory losses. The IRS treats them just like any other business that has unsold merchandise - once the event passes, those tickets have zero fair market value. For your Taylor Swift tickets specifically, since you bought them with the intent to resell (even if it was just part of your side business), they qualify as business inventory. When they went unused, that's a $280 loss you can absolutely deduct against your ticket reselling profits. The most important thing is maintaining good records. I always keep: - Original purchase confirmations/receipts - Screenshots of any sales attempts (StubHub listings, Facebook posts, texts to potential buyers) - Documentation of the event date passing - Bank statements showing the purchase One thing I learned the hard way - don't wait too long to claim these losses. File them in the tax year the event occurred, not when you finally give up trying to sell them. So those Taylor Swift tickets from this year should be claimed on your 2024 return. The fact that you're making legitimate profits from successful flips shows clear business intent, which is exactly what the IRS looks for to distinguish this from hobby activity.

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Thais Soares

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This is exactly the kind of detailed guidance I was hoping to find! I'm just getting started with ticket reselling and have been really nervous about the tax implications. Your point about filing losses in the tax year the event occurred is super helpful - I was wondering about the timing on that. Quick question: when you mention "screenshots of sales attempts," how extensive does that documentation need to be? Like if I listed tickets on StubHub for a week and got no bites, is just a screenshot of the listing sufficient? Or should I be keeping more detailed records of price changes, views, etc.? Also, do you typically use tax software that handles Schedule C easily, or do you work with an accountant for this kind of side business? I'm trying to figure out the most efficient way to handle everything come tax time.

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Natalie Khan

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I've been dealing with similar ticket reselling tax questions and wanted to share what I learned from my accountant. The unsold ticket deduction is definitely legitimate, but there's one important detail that hasn't been mentioned yet - you need to be careful about how you classify yourself. If this is truly a "side gig" like you mentioned, make sure you're prepared to demonstrate business intent to the IRS. They look for things like: keeping business records, having a separate business bank account (even if it's just a designated checking account), treating it consistently as a business activity, and making genuine efforts to be profitable. For your $280 Taylor Swift tickets, absolutely claim that loss. But also document WHY they went unsold - was it because the market price dropped below what you paid? Did you list them but get no buyers? This kind of documentation helps establish that you were genuinely trying to operate a business, not just buying tickets speculatively. One more tip: consider tracking your time spent on this activity. Even if it's just a few hours a week, having a log of time spent researching, listing, communicating with buyers, etc. can help support the business classification if you ever need to justify it. The tax savings from properly deducting these losses can be significant, so it's definitely worth doing it right!

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This is really comprehensive advice, thank you! The point about demonstrating business intent is something I hadn't fully considered. I've been pretty casual about record-keeping so far, but it sounds like I need to get more organized if I want to properly claim these deductions. For the Taylor Swift tickets specifically, they went unsold because the resale market completely crashed after the original sale date - people were selling similar seats for way less than I paid by the time I tried to list them. I do have some screenshots of the StubHub listings where I tried different price points, so hopefully that shows I was genuinely attempting to sell them as business inventory. The separate business bank account suggestion is smart. I've been mixing everything with my personal account, which probably doesn't look very professional from a business standpoint. Would it be worth setting that up retroactively, or should I just start doing it going forward for next year? Also, regarding the time tracking - do you know if there's a minimum number of hours or frequency that would help establish this as a legitimate business rather than just occasional hobby activity?

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Miguel, don't feel embarrassed at all - partnership taxation is genuinely complex and your questions are spot on! I went through this exact same confusion when our small consulting group formed an LLC. You're absolutely right that you'll file Form 1065 and each partner will get a K-1. When you file your personal 1040, the K-1 income/loss goes on Schedule E (Supplemental Income), NOT Schedule C. This is a crucial distinction - Schedule C is only for sole proprietorships. For those business expenses you mentioned (car, equipment), here's what I learned: these should be handled at the partnership level on the 1065, not on your personal returns. The partnership takes the deduction, then your share of the reduced profit flows to your K-1. If you've already paid for business stuff personally, you have two clean options: 1. Have the LLC reimburse you (with receipts and documentation) 2. Treat it as a capital contribution to the partnership Either way, the deduction happens on the 1065. Don't try to deduct business expenses on your personal return while also reporting K-1 partnership income - that mixes two different tax treatments and can raise red flags. My biggest recommendation: set up an expense reimbursement policy in your operating agreement ASAP. It'll save you headaches down the road and create the paper trail you need for tax compliance.

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This is exactly the kind of clear explanation I needed! I'm in a similar situation with a small LLC and was getting overwhelmed by all the different advice online. The distinction between Schedule E vs Schedule C makes so much sense now - I was definitely heading toward the wrong path there. Quick follow-up question: when you set up your expense reimbursement policy, did you include any specific requirements for documentation? I'm thinking about things like mileage logs, receipt requirements, approval processes, etc. Our group is pretty informal right now but I can see how having clear rules would prevent confusion later. Also, how quickly did you typically reimburse partners? I'm wondering if there are any tax implications to timing - like if I pay for something in December but don't get reimbursed until February of the next tax year.

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@Lauren Johnson Great questions about the expense reimbursement policy! When we set ours up, we included several key requirements: Documentation: All expenses over $25 need receipts, business purpose description, and dates. For mileage, we require a simple log with date, destination, business purpose, and miles. We use a shared Google Sheet template that makes it easy. Approval: Expenses under $500 can be submitted directly for reimbursement. Anything over $500 needs pre-approval from at least two partners to prevent surprises. Timing: We do monthly reimbursements by the 15th of the following month. The timing across tax years generally isn t'an issue since the partnership is reporting on a cash basis - what matters is when the partnership actually pays the expense or reimburses it. One thing we learned: be specific about what counts as reimbursable. We had some awkward conversations early on about meals, home office expenses, and personal vehicle use. Now our operating agreement spells out exactly what s'covered and what documentation is needed. The key is keeping it simple enough that people will actually follow it, but detailed enough to satisfy IRS requirements if you ever get audited. Having clear rules from the start prevents the creative "interpretations that" can cause problems later!

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Anita George

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I just went through this exact situation with my 4-member LLC last tax season and wanted to share what worked for us! The learning curve is steep but totally manageable once you get the basics down. First, you're on the right track with Form 1065 and K-1s. Each partner reports their K-1 income on Schedule E of their personal 1040 - definitely NOT Schedule C. I made that mistake initially and had to amend my return. For business expenses paid personally, we developed a simple system: anything under $100 gets submitted monthly for reimbursement with just a receipt and quick description. Larger expenses need pre-approval via our group chat. The LLC reimburses within 30 days and takes the deduction on the 1065. One thing that really helped us was opening a dedicated LLC business account and credit card right away. It makes tracking partnership expenses so much cleaner than trying to sort through personal purchases later. Also, don't stress too much about getting everything perfect in year one. We made some mistakes with expense categorization and documentation, but we learned from them and tightened up our processes. The important thing is establishing good habits early and being consistent about separating partnership business from personal finances. Your friend group LLC sounds like it's starting off on the right foot by asking these questions upfront!

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