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Ask the community...

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  • DO NOT post call problems here - there is a support tab at the top for that :)

tbh ur better off faxing them. at least u know someone has to physically touch the paper eventually lol

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Ava Johnson

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Another trick that worked for me: try calling the business tax line at 1-800-829-4933 and ask them to transfer you to individual tax help. Sometimes they can bypass the main queue. Also downloaded the IRS2Go app which at least shows your refund status without having to call - might save you some frustration while you're waiting to get through!

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Paloma Clark

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Just wanted to add that the IRS actually does process paper Form 1065s much slower than electronic filings - typically 8-12 weeks versus 2-3 weeks for e-filed returns. So don't panic if you don't hear anything for a while after mailing. One tip I learned the hard way: make sure you sign and date the form in blue ink, not black. The IRS scanning equipment apparently has trouble distinguishing black ink signatures from photocopied signatures, which can delay processing. Also double-check that you've included Form 8832 if you're electing partnership tax treatment for your LLC - that's a common oversight that can cause headaches later. Good luck with your filing! Paper filing definitely works, it just takes patience.

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Liam Brown

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Thanks for the blue ink tip! I had no idea that could be an issue. Quick question - when you mention Form 8832 for electing partnership treatment, is that required even if we already indicated partnership tax treatment when we got our EIN? We set up our LLC last year and I thought we already made that election with the IRS when we applied for our tax ID number.

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Omar Farouk

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Great question about Form 8832! If your LLC has more than one member (which yours does with 4 partners), the IRS automatically treats it as a partnership for tax purposes by default - no election needed. Form 8832 is only required if you want to elect a DIFFERENT tax treatment (like corporate taxation). So if you want partnership treatment (which is the default for multi-member LLCs), you don't need to file Form 8832 at all. You can just proceed with filing your Form 1065. The fact that you got an EIN doesn't constitute making any particular tax election - that's just getting a tax ID number. However, if you ever want to change your tax classification in the future (say, elect S-corp treatment), THEN you'd need to file Form 8832 or Form 2553. But for now, you're all set without any additional election forms!

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Paolo Conti

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Don't forget that the documentation matters as much as the classification! Regardless of whether you claim 50% or 100%, always record: 1. Who attended 2. Business purpose discussed 3. Date and location 4. Cost amount I learned this the hard way when I got a notice from the IRS questioning my meal deductions. Having a calendar invite showing "Board Meeting with Joe" wasn't enough. Now I take notes during meals and snap a pic of the receipt with my notes.

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Amina Sow

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Does anyone use an app for tracking this? Writing notes on receipts seems so 1990s lol. There's gotta be a better way!

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@Amina Sow I use Expensify for tracking meal expenses and it s'been a game changer! You can snap photos of receipts, add voice notes about the business purpose right after the meal, and it automatically pulls location data. Plus it integrates with most accounting software. The voice-to-text feature is perfect for quickly recording discussed "Q2 marketing strategy with board member Sarah while" it s'fresh in your mind. Way more efficient than handwritten notes and creates a digital paper trail that s'IRS-friendly.

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Great question! As someone who's dealt with this exact scenario, the key distinction is employment status, not board membership. Board members who aren't on your W-2 payroll are generally limited to the 50% deduction, even if they're shareholders. However, there are a few nuances worth considering: 1. **Timing matters**: If the meal occurs during an official board meeting where you're providing food as part of the meeting (similar to providing refreshments), this could potentially be treated differently than a casual business lunch. 2. **Documentation is critical**: Keep detailed records showing the business purpose, attendees, topics discussed, and how it relates to your S-Corp operations. This becomes especially important if the IRS questions your deductions. 3. **Consider the bigger picture**: While you might be limited to 50% on these specific meals, make sure you're capturing all legitimate business meal expenses throughout the year - they add up quickly. One tip: If your board meetings involve multiple people (other board members, key employees), the dynamics of the deduction might change. But for one-on-one advisory meals with non-employee board members, 50% is typically the safe approach. Always consult with your tax professional for your specific situation, but this framework should help you categorize these expenses appropriately.

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Gabriel Ruiz

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This is really helpful guidance! I'm curious about the "timing matters" point you mentioned regarding official board meetings. If I'm understanding correctly, would providing lunch during a formal quarterly board meeting be treated more favorably than taking a board member out to lunch to discuss the same topics? I'm wondering if the formal meeting structure itself changes the deduction rules, or if it's more about having proper documentation of the business purpose regardless of the setting.

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Marilyn Dixon

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As a newcomer to this community, I want to thank everyone for this incredibly thorough discussion! I'm also planning to give a performance bonus to one of my 1099 contractors and was completely unsure about the proper approach. The consensus here is crystal clear: treat it as additional compensation, document the business justification, report it on the 1099-NEC with all other payments, and communicate transparently with the contractor about timing and tax implications. What really stands out to me is how much contractors seem to appreciate the transparency and consideration for their tax planning needs. I had initially worried that bringing up tax implications might make the bonus feel less generous, but it sounds like it actually shows respect for their business operations. I'm particularly grateful for the practical tips about timing (asking about quarterly payment preferences), documentation (specific but not overly complex business justifications), and communication (explaining what impressed you and that it will be on the 1099-NEC). One final question for the group - for those who've done this multiple times, do you find it gets easier to have these conversations with contractors about bonuses and timing, or does it always require some coordination? I want to set up good practices from the start!

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Carmen Lopez

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Welcome to the community! It definitely gets easier over time. After doing this a few times, I've found that contractors really appreciate when you establish a pattern of clear communication about these things. Now I just send a quick message when I'm planning a bonus that says something like "Hey [Name], I'd like to give you a performance bonus for your great work on [specific project]. Would you prefer to receive it this quarter or early next quarter for your tax planning? And just so you know, I'll include it on your 1099-NEC as additional compensation." Most contractors now just tell me their preference right away because they know I'll ask. It's become a really smooth process, and I think it actually strengthens our working relationships because they see that I'm considerate of their business needs. The initial conversations might feel a bit formal, but it quickly becomes just part of how you do business together. You're smart to think about establishing good practices from the start - your contractors will definitely notice and appreciate the professionalism!

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As a newcomer to this community, I wanted to share my recent experience with giving a contractor bonus that might be helpful to others in similar situations. I was in the exact same position as Oliver a few months ago - wanting to reward an outstanding 1099 contractor but being completely unsure about the tax implications. After doing research similar to what's been discussed here, I decided to go ahead with additional compensation rather than trying to find ways around it. What I learned is that being straightforward about it being taxable income actually made my contractor more confident in our business relationship, not less. When I reached out to discuss timing, they told me they really appreciated that I understood how their tax planning works and were considerate of their quarterly payments. I ended up giving the bonus in early December with a note explaining it was for their exceptional project management skills that saved us two weeks on our biggest client deliverable. They were thrilled, and when tax season came around, there were zero complications because everything was properly documented and expected. The key insight for me was that treating contractors as the business professionals they are - which includes being transparent about tax implications - actually makes these gestures more meaningful, not less. Your contractor will likely appreciate both the recognition and the professional way you're handling it!

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Has anyone used TurboTax to report RSUs? I'm having this same issue and wondering if there's a specific way to enter this in TurboTax to make sure it's handled correctly. Every time I try, it seems like I'm getting double-taxed on the RSU income.

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QuantumQuest

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I use TurboTax every year for my RSUs. The key is when entering your 1099-B, make sure to check the box that says "This sale is related to compensation you received" or something similar. Then it will prompt you to enter the compensation amount already included in your W2. The trick is to make sure you're entering the basis adjustment for each specific lot of RSUs that was sold.

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Carmen Diaz

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This is a really common RSU reporting confusion! Let me break this down step by step: The $16,000 on your W2 represents the fair market value of your RSUs when they vested - this is already included in your taxable income (Box 1 of your W2). You've already paid taxes on this amount. The $9,000 on your 1099-B is what you actually received when you sold the shares. The "missing" $7,000 is most likely due to: 1. Tax withholding - your company probably sold some shares automatically to cover your tax obligation 2. Possible trading fees or timing differences For your tax return, you need to: 1. Report the stock sale on Schedule D/Form 8949 using the $9,000 proceeds 2. Your cost basis should be the portion of the $16,000 that corresponds to the shares you actually received and sold 3. If you sold immediately after vesting with minimal gain/loss, your cost basis should be very close to the $9,000 proceeds The key is making sure you don't get double-taxed on the RSU income that's already in your W2. Check your brokerage statements for any "tax withholding" or "shares sold to cover taxes" entries around the vesting date - that will explain the difference.

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Luca Romano

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This is exactly the clear explanation I needed! I was getting so frustrated trying to understand where that $7,000 went. Your breakdown makes perfect sense - I bet my company did withhold shares for taxes and I just didn't notice it on my statements. I'm going to go back and look for those "shares sold to cover taxes" entries you mentioned. It's such a relief to know that I'm not missing something obvious and that this discrepancy is actually normal. The double taxation concern was really stressing me out. One quick follow-up - when you say the cost basis should be "the portion of the $16,000 that corresponds to the shares you actually received," how do I calculate that exactly? Is it just a simple ratio based on the dollar amounts?

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