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I've been dealing with IRS issues for years and your situation is unfortunately very common. The good news is that your transcript codes clearly show the IRS has record of both payments, so you have strong documentation on your side. A few additional things to consider: First, since you moved in July 2024, double-check that the IRS has your current address for refund purposes. Even if you updated it online, there can be timing issues with when different IRS systems sync up. You can verify this by calling or checking your online account. Second, after 6 months with no resolution, you're definitely in Taxpayer Advocate Service territory. They're specifically designed for cases where normal IRS processes have failed. Call them at 1-877-777-4778 and explain you've been waiting 6 months for a refund of a duplicate payment. Third, don't forget to ask about interest when you finally get this resolved. The IRS pays interest on overpayments that take an unreasonably long time to process, and 6 months definitely qualifies. The transcript codes you found (670 and 610) are actually really helpful - lead with those when you call because it shows you understand their system and have done your homework. This isn't your fault, and you shouldn't have to jump through hoops to get your own money back. Stay persistent!

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This is exactly the kind of detailed guidance I wish I'd had when this whole mess started! The point about IRS systems not syncing up properly really resonates - I bet that's exactly what happened with my address update. I updated it online in August, but if they had already processed (or attempted to process) my refund to the old address before then, that would explain the delay. I'm definitely going to call the Taxpayer Advocate Service this week. It's reassuring to know that 6 months is considered unreasonably long even by IRS standards. And you're absolutely right about asking for interest - at this point they've had my $1,227 for half a year when it should have been a simple refund process. Thanks for emphasizing the importance of those transcript codes too. I'll make sure to lead with "I have a 670 and 610 code for the same tax obligation" right off the bat. It sounds like that immediately signals to them that this is a legitimate duplicate payment issue, not just someone confused about their taxes. Really appreciate all the specific advice!

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I went through almost the exact same situation two years ago - double charged $1,845 and it took nearly 8 months to resolve. The most important thing to know is that you're absolutely entitled to that money back, and the transcript codes you found (670 and 610) are actually perfect evidence that the IRS recognizes both payments. Here's what finally worked for me: I called the Taxpayer Advocate Service at 1-877-777-4778 after months of getting nowhere with regular IRS phone lines. Since you've been waiting 6 months with no resolution, your case definitely qualifies for their help. They can actually expedite cases that have been stuck in the system too long. When you do get through to someone (whether TAS or regular IRS), lead with those transcript codes immediately. Say something like "I have both a 670 and 610 code on my transcript for the same tax obligation - this shows a duplicate payment that needs to be refunded." This demonstrates you understand their system and aren't just confused. Also, since you moved in July but filed in February, there's a very good chance your refund check was sent to your old address and got lost in the mail. Make sure to specifically ask what address they have on file for your refund - this could be the root cause of the delay. Don't give up! After this much time, you may also be entitled to interest on the overpayment. The IRS definitely made an error here, and you shouldn't have to suffer financially for their mistake.

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Isaiah Cross

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As a newcomer to this community, I've been following this discussion with great interest and want to thank everyone for sharing such detailed, practical insights about golf entertainment deductions. The depth of real-world experience shared here is invaluable! What I'm taking away from this thread is that the IRS rules create a challenging cost-benefit equation for most business owners. The fact that membership dues are completely non-deductible, combined with the 50% limitation on qualifying entertainment expenses and the extensive documentation requirements, means the actual tax savings are often quite modest relative to the compliance burden. I'm particularly struck by the audit experiences shared here - it's clear that the IRS scrutinizes these deductions heavily, looking not just at documentation but also at patterns, frequency, and reasonableness relative to income and industry. The shift from simply keeping receipts to maintaining contemporaneous records with business purpose, attendee details, and follow-up outcomes represents a significant administrative commitment. For someone just starting to navigate business deductions, this thread reinforces the wisdom of focusing on clear-cut categories first before venturing into more complex areas like entertainment expenses. The peace of mind from staying in clearly compliant territory often outweighs the marginal tax benefits from aggressive deductions, especially given how much the landscape has changed since the Tax Cuts and Jobs Act. Thanks again to everyone who shared their experiences - this has been an excellent introduction to the practical realities of business tax compliance!

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Welcome to the community @Isaiah Cross! Your summary perfectly captures the key takeaways from this extensive discussion. As someone also new here, I really appreciate how you've distilled the complex advice into actionable insights. What resonates most with me is your point about the "challenging cost-benefit equation." When you break down the actual numbers - membership dues completely non-deductible, only 50% of qualifying expenses deductible, extensive documentation requirements, and significant audit risk - it becomes clear why many experienced members here recommend starting conservative with business deductions. The evolution from simple receipt-keeping to the detailed contemporaneous documentation standards described here (timestamped records, business purpose notes, follow-up emails, pattern awareness) really illustrates how much more complex tax compliance has become, especially post-Tax Cuts and Jobs Act. I'm particularly grateful for the practical documentation strategies shared throughout this thread - the voice memo techniques, digital photo workflows, and email trail methods provide a roadmap for anyone who does decide to pursue these deductions despite the complexities. Your advice about focusing on clear-cut deduction categories first is exactly what I needed to hear as I plan my business tax strategy. It's better to be conservative and compliant than to chase marginal savings that could create audit headaches down the road. This community clearly has incredible practical expertise - looking forward to learning more!

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As someone new to this community, I've been thoroughly impressed by the detailed and practical advice shared throughout this thread! The collective expertise here has really clarified the complex landscape of golf-related business deductions. What stands out most to me is how the IRS has created such a narrow window for legitimate deductions in this area. The complete prohibition on membership dues, combined with the 50% limitation on qualifying entertainment expenses and the extensive documentation requirements, means we're often talking about very modest tax savings relative to a significant compliance burden. I'm particularly grateful for the real audit experiences shared here - they paint a clear picture of how thoroughly the IRS scrutinizes these deductions. The fact that agents look at patterns, frequency, reasonableness relative to income, and even cross-reference with business outcomes shows this isn't just about keeping receipts anymore. For newcomers like myself, the advice to start with clear-cut business deductions before venturing into entertainment expenses makes perfect sense. The administrative overhead of maintaining contemporaneous documentation (with all the timestamped photos, business purpose notes, follow-up emails, and pattern management) seems substantial for what might amount to a few hundred dollars in tax savings annually. The practical documentation strategies shared here are invaluable though - voice memos, digital workflows, and email trails provide a solid framework for anyone who does choose to pursue these deductions. Thanks to everyone who shared their hard-won expertise!

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Welcome to the community @Liam Fitzgerald! Your thorough analysis really captures the essence of what makes entertainment deductions so challenging. As another newcomer, I'm struck by how this thread has evolved into such a comprehensive guide for understanding the practical realities of business tax compliance. What I find most valuable is how everyone has shared not just the rules, but the real-world implications - the time investment, audit risks, and actual dollar amounts we're talking about. Your point about "very modest tax savings relative to significant compliance burden" really drives home why so many experienced members here recommend the conservative approach. I'm also impressed by how the community has laid out such clear progression for new business owners: master the straightforward deductions first (office supplies, software, clear business meals), then consider more complex areas like entertainment only if the amounts justify the administrative overhead. The documentation strategies shared throughout this thread - from voice memos to timestamped digital records - show that while compliance is possible, it requires a systematic approach that many small business owners might find overwhelming relative to the potential benefits. Thanks for synthesizing all this advice so clearly. For those of us just starting our business tax journey, having this kind of practical framework is incredibly valuable for making informed decisions about which deductions are worth pursuing!

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Here's a quick checklist I use for my rental properties that might help with the 1099-NEC vs 1099-MISC confusion: 1099-NEC is used for: - Independent contractors (handymen, plumbers, electricians) - Service providers (lawn care, snow removal, cleaning) - Property managers (if not a corporation) 1099-MISC is used for: - Rent payments YOU make to someone else - Attorney fees (over $600, even if they're a corporation) - Prizes or awards you give out And remember, neither form is needed if: - You paid less than $600 in the year - You paid via credit card/PayPal (the processor sends a 1099-K) - The recipient is a corporation (except attorneys

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Nia Williams

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This is helpful! But I'm still confused about property management companies. Mine is an LLC but I have no idea if they're taxed as a corporation or partnership. They've managed my rental for years and I've never sent them a 1099. Should I be concerned?

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You should definitely request a W-9 from your property management company! Property management fees are one of the most commonly missed 1099-NEC requirements for landlords. If they're an LLC taxed as a partnership or sole proprietorship, you should have been sending them 1099-NECs all along. The good news is that the IRS doesn't usually go after landlords retroactively for missing 1099s unless there's an audit, but you want to get compliant going forward. Request their W-9 now and start issuing them properly for this tax year. If they refuse to provide a W-9, that's actually a red flag and you should consider finding a new property manager. Most legitimate property management companies will provide a W-9 without any issues - they deal with this request from landlords all the time.

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Great question about 1099-NEC vs 1099-MISC! I went through this exact same confusion last year with my rental properties. The key thing that helped me was understanding that 1099-NEC replaced most uses of 1099-MISC for services. So for your contractors, plumbers, electricians, and maintenance folks, you'll use 1099-NEC (not 1099-MISC) for payments over $600. Regarding the corporation vs non-corporation issue - this tripped me up too! Here's what I learned: **You DO need to send 1099-NEC to:** - Sole proprietors (individuals) - Single-member LLCs (unless they elect corporate tax treatment) - Multi-member LLCs taxed as partnerships - General partnerships **You DON'T need to send 1099-NEC to:** - C-Corporations - S-Corporations - LLCs that have elected to be taxed as corporations The tricky part is that just because someone has an LLC doesn't automatically make them a corporation for tax purposes. Many LLCs are actually taxed as sole proprietorships or partnerships. My advice: Always request a W-9 form BEFORE paying any contractor. Box 3 on the W-9 will tell you exactly how they're classified for tax purposes. If you've already paid someone without getting a W-9, request it now - better late than never! Don't stress too much about past years, but definitely get compliant going forward. The penalties for missing 1099s can add up quickly.

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Diego Rojas

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This is exactly the breakdown I needed! I've been so overwhelmed trying to figure this out. Quick follow-up question - when you say "LLCs that have elected to be taxed as corporations," how would I know if they made that election? Would that show up on their W-9 form, or is there another way to tell? I have a few LLC contractors and I want to make sure I'm handling this correctly going forward.

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Mei Wong

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I went through this exact same issue last month and it was incredibly frustrating! After trying all the standard troubleshooting steps (clearing cache, different browsers, etc.), what finally worked for me was a combination of things. First, I completely logged out of ALL IRS-related sites (not just Free File, but also IRS.gov if you've been checking your account status there). Then I cleared all cookies specifically for irs.gov and freefile.intuit.com domains - not just a general browser clear, but targeted cookie removal. The key breakthrough was when I realized my antivirus software was blocking certain scripts from running properly on the Free File site. I had to temporarily add the Free File domain to my antivirus whitelist. After doing that and restarting my browser completely (not just closing tabs), I was able to log in successfully. Also, double-check that you're going directly to the official Free File site through IRS.gov and not through a search engine result. There are some unofficial sites that look very similar but have slightly different authentication systems that can cause these mysterious login failures. Your saved data should definitely still be there once you get back in - the IRS systems keep that information separate from the login credentials. Don't give up! I know how stressful it is when you've already put in all that work.

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This is incredibly thorough advice - thank you so much for sharing your experience! The antivirus blocking issue is something I never would have considered. I use Norton and it's definitely strict about blocking scripts, so I'll try whitelisting the Free File domain. Your point about logging out of ALL IRS-related sites is really smart too. I've been checking my refund status on IRS.gov while trying to troubleshoot this Free File issue, so there might be some kind of session conflict happening between the different IRS systems. The targeted cookie clearing approach sounds much more precise than just doing a general browser clear. Do you remember which specific domains you had to clear cookies for beyond irs.gov and freefile.intuit.com? I want to make sure I'm being thorough. It's reassuring to hear that your saved data was still there after resolving the login issue. That's been my biggest worry throughout this whole ordeal - losing all the work I've already put in. Thanks for taking the time to write out such detailed steps!

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I've been following this thread and wanted to share another potential fix that worked for me recently. If you're still having the password field clearing issue, try accessing Free File Fillable Forms through the IRS2Go mobile app instead of the web browser. I know it sounds counterintuitive to use a mobile app for tax filing, but the authentication system seems to be more stable there. I was able to log in through the app, verify my account was working, and then mysteriously the web version started working again too. It's like the mobile login somehow reset whatever was causing the web browser authentication to fail. Also, if you're using Windows, try running your browser as administrator. Right-click on your browser icon and select "Run as administrator" before attempting to log in. Sometimes Windows security settings can interfere with the authentication process in subtle ways that don't generate obvious error messages. One more thing - check if your internet connection is going through any corporate firewalls or content filters. I had a friend who couldn't access Free File from his work-from-home setup because his company's VPN was blocking certain authentication protocols. When he switched to his personal internet connection, everything worked fine. The good news is that almost everyone who's posted about this issue has eventually found a solution, so don't lose hope! Your data should definitely still be there waiting for you.

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Carmen Diaz

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Does anyone know if FreeTaxUSA has a way to import W-2s directly? I'm doing my taxes for the first time too and I really don't want to type everything in manually...especially all these weird codes in different boxes. My W-2 has like 6 different things in Box 14 alone!

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FreeTaxUSA doesn't have W-2 import like some of the more expensive software. You have to enter everything manually. But honestly it's not that bad, just takes like 10-15 mins per W-2. And for Box 14 stuff - if you're taking standard deduction you can basically ignore everything there unless you're in a state that has special deductions for them.

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Olivia Clark

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Hey there! Don't stress too much about Box 14 - it's one of those things that seems scary but is usually pretty straightforward for most people. For your specific items: - "UNION DUES" - These are the union membership fees deducted from your paycheck. Generally not deductible on federal taxes unless you itemize (which you probably won't as a first-time filer). - "VOL LIFE" - This is voluntary life insurance premiums you're paying through payroll deduction. Also not deductible. Since you're using FreeTaxUSA and likely taking the standard deduction, you can safely ignore both of these items for your federal return. The software will ask you about itemizing vs. standard deduction, and it'll automatically choose whichever saves you more money (almost always standard deduction for someone in your situation). The main thing to remember is that Box 14 is mostly informational - it shows what was deducted from your pay, but doesn't usually affect your tax calculation. You're doing great by being careful and asking questions! That's exactly the right approach for your first time filing.

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