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Worried about 1099-K tax reporting for selling personal items on eBay & PayPal (yard sale stuff)

I'm really stressing out about this 1099-K situation for 2025. So the threshold is supposed to be $5000 this year, but I'm hearing mixed things. I'm not trying to avoid paying taxes on actual profit - that's not my issue at all. I'm literally just selling my old personal belongings at a loss to help pay some bills. For example, I'm currently selling a designer bag on eBay for $75 that I originally paid around $400 for a few years ago. Nobody wants to pay more, and I desperately need to cover some expenses. If I was actually making money on these sales, I'd happily report the profits! I've sold roughly $2200 worth of my personal stuff this year. I've heard PayPal is already sending 1099-Ks at $600 despite the $5000 threshold, while eBay is sticking with the $5000 limit. My biggest worry is what happens if they send me a form anyway or if I end up selling more than expected. The real problem is I don't have receipts from years ago for most of these items. How am I supposed to prove these were personal items sold at a loss? I keep seeing people say this is straightforward, but for someone like me who uses the free IRS filing system or TurboTax because I can't afford an accountant, this is super confusing. I'm terrified of being audited and then having to pay taxes on money that wasn't actually income but just me desperately selling my stuff for less than I paid. Any advice would be really appreciated!

Hannah Flores

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I'm having exact same problem!!! Last month I sold my grandmother's old china set for $700 that was probably worth thousands when new but I don't have a receipt from the 1970s lol. Also sold some designer clothes I impulse bought and never wore but took a big loss on them. How do u even figure the cost basis on inherited items like that china? Its so confusing and I'm scared PayPal will send a 1099K even though I'm nowhere near the threshold and then the IRS will think I'm running a business or something which I'm definitely not!!!

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Natalie Adams

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For inherited items like your grandmother's china, you can use what's called "fair market value" at the time you inherited them. You don't need the original receipt from the 1970s. You can research similar vintage china sets on sites like eBay or antique sites to establish a reasonable value. For the designer clothes, you can use credit card statements, email confirmations, or even screenshots of the current retail price of similar new items to establish that you sold them at a loss. The key is making a good faith effort to document these were personal items sold at a loss. Even without perfect documentation, creating this kind of reasonable basis for your claims is typically sufficient for the IRS.

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Amara Nnamani

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@Jordan Walker, I completely understand your stress about this! I went through something very similar last year and want to share what I learned that might help ease your worries. First, the good news: you're thinking about this correctly. The IRS distinguishes between personal items sold at a loss versus actual business income, and you won't owe taxes on selling your personal belongings for less than you paid. Here's what I did when I was in your exact situation: 1. Created a simple spreadsheet with columns for: Item Description, Approximate Purchase Date, Estimated Original Cost, Sale Price, and Notes 2. For items without receipts, I researched similar items online to estimate what I originally paid 3. Added notes like "personal designer bag purchased approximately 2019, selling due to financial need" The key insight that helped me: the IRS isn't trying to trap people selling personal items at yard sale prices. They're looking for patterns that suggest unreported business activity. Your situation - selling varied personal items at obvious losses - is clearly not a business. Regarding the thresholds, yes it's confusing! PayPal has been more aggressive with 1099-K reporting, but remember: receiving the form doesn't create a tax obligation. You'll just need to show these were non-taxable personal sales when you file. Don't let this keep you from selling items you need to sell! Just document what you can reasonably document, and you'll be fine.

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Callum Savage

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@Amara Nnamani This is exactly the kind of practical advice I was hoping for! Thank you for breaking it down so clearly. I m'definitely going to create that spreadsheet you mentioned - having that structure makes it feel much more manageable. One quick follow-up question: when you researched similar items online to estimate original costs, did you use current prices or try to find historical pricing? Like for that designer bag I mentioned, should I look up what similar bags cost now or try to figure out what they cost a few years ago when I bought it? Also, I really appreciate you pointing out that the IRS isn t'trying to trap people in my situation. That helps calm my anxiety a lot. I think I was getting overwhelmed by all the conflicting information online and started catastrophizing about worst-case scenarios.

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Sofia Peña

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As someone who's just beginning to navigate trust taxation issues after recently inheriting property through a family trust, I've been reading through this entire discussion with great fascination and, honestly, quite a bit of anxiety about the complexity involved. The stepped-up basis rules for trust-held property seem incredibly nuanced, and what really stands out to me from everyone's shared experiences is how often initial professional advice turned out to be incorrect - leading to families discovering they could save tens of thousands of dollars by getting proper specialized review. I'm particularly struck by how consistently everyone recommends using both an estate tax attorney AND a CPA with trust specialization to review the situation independently. That dual-perspective approach seems crucial for catching details that might be missed with just one professional opinion. For the original poster with such significant property appreciation ($95K to $710K), the potential tax implications of getting the basis calculation wrong could indeed be enormous. Based on everything I've read here, the investment in specialized professional analysis before proceeding with any sale seems absolutely essential. As someone completely new to this, I'm wondering - beyond the credentials people have mentioned (ABV for CPAs, ACTEC fellowship for attorneys), are there any specific questions you'd recommend asking potential professionals during initial consultations to gauge whether they truly have the depth of experience needed for complex trust matters? The financial stakes are clearly high enough to justify being very thorough in selecting the right expertise. Thank you all for creating such a valuable resource for families dealing with these challenging situations during already difficult times.

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Freya Ross

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Welcome to the community, Sofia! As someone who's also relatively new to trust taxation, your question about specific questions to ask professionals is really valuable. From what I've learned reading through this discussion, here are some key questions that seem to help identify truly specialized expertise: "How many irrevocable trust stepped-up basis cases have you handled in the past two years?" Look for specific numbers, not vague answers. "Can you walk me through the difference between how basis step-up works for QTIP trusts versus bypass trusts versus grantor trusts?" Their ability to clearly explain these distinctions seems to be a good indicator of depth of knowledge. "What specific provisions in trust language do you look for that might affect basis step-up calculations?" The specialists mentioned in this thread seem to know exactly what clauses to examine. "Can you provide references from families who've dealt with similar trust property situations?" Reputable professionals with real experience should be able to connect you with past clients (with permission). Also, I'd suggest asking them to explain their review process - do they examine just the original trust document, or do they also look for amendments? Do they coordinate with other professionals when needed? The pattern from everyone's experiences here suggests that the professionals who can give specific, detailed answers to these questions are the ones who end up finding those valuable provisions that save families thousands in taxes. The investment in thorough vetting upfront seems so worth it given the stakes involved!

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As someone who's completely new to trust taxation after recently becoming a beneficiary of a family trust, I've been following this discussion with both fascination and some concern about the complexity involved. The stepped-up basis rules for trust-held property are far more intricate than I initially understood. What really stands out from reading everyone's experiences is how frequently initial professional advice turned out to be incomplete or incorrect, with families later discovering they could save significant amounts through proper specialized analysis. The pattern of people saving $20K-40K+ by getting the basis calculation right really drives home the importance of this issue. I'm particularly impressed by the consistent recommendation to use both an estate tax attorney AND a CPA with trust specialization working independently but coordinating together. That dual-perspective approach seems essential for identifying nuances that single professional reviews might miss. For the original poster dealing with such substantial property appreciation ($95K to $710K), the difference between getting a partial versus full stepped-up basis could indeed represent life-changing money in tax implications. Given all the experiences shared here, investing in specialized professional review before any sale decision seems absolutely crucial. As someone just starting this journey, I'm grateful for all the practical advice shared - from specific credentials to look for (ABV, ACTEC) to the importance of reviewing both original trust documents and any amendments. The financial stakes clearly justify being very thorough in selecting the right expertise. This community has been an invaluable resource for understanding these complex matters during what I know is already a difficult time for families dealing with both loss and major financial decisions.

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Diego Vargas

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I've been researching similar options and wanted to add a few considerations that might help. One approach I've found is looking into conservation easements - if you donate development rights on your land to a qualified organization, you can often get significant property tax reductions (sometimes 50-80% depending on the state) while still maintaining ownership and the right to live there. Another option worth exploring is homesteading exemptions, which many states offer but don't widely advertise. Texas, for example, has a homestead exemption that can reduce your taxable property value by up to $25,000 for school taxes, and some counties offer additional exemptions for veterans, seniors, or disabled individuals. Also, regarding the Alaska suggestion - while those remote parcels sound appealing, make sure you understand the access requirements. Many of these properties are only accessible by plane or boat, which can make year-round living extremely expensive and potentially dangerous during emergencies. The "no property tax" benefit might be offset by the costs of maintaining access and emergency preparedness. One more thought: if you're willing to consider a mobile lifestyle, some states like South Dakota, Texas, and Florida are popular with full-time RVers because they offer legal residency without requiring you to own property, and you can establish domicile there while traveling. This eliminates property tax entirely while maintaining US residency.

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Connor Murphy

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Thanks for the comprehensive overview, Diego! The conservation easement approach is particularly interesting - I hadn't considered that option. Do you know if there are any restrictions on what types of improvements you can make to the property once you've donated the development rights? I'm wondering if things like adding solar panels, expanding existing structures, or building additional outbuildings would be affected by the easement terms. Also, regarding the South Dakota domicile strategy - how does that work practically for someone who wants to eventually settle down permanently? Is it more of a temporary solution while you're searching for the right property to purchase, or can you maintain that arrangement long-term?

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Great questions, Connor! For conservation easements, the restrictions really depend on the specific terms negotiated with the conservation organization. Most easements I've researched allow maintenance and reasonable improvements to existing structures, and solar panels are typically permitted since they're considered environmentally beneficial. However, you'd usually be restricted from subdividing the land or building new primary structures. The key is working with an experienced attorney during the easement negotiation to ensure the terms align with your long-term plans. Regarding South Dakota domicile - it's actually quite sustainable long-term if you embrace a mobile lifestyle. Many full-time RVers maintain SD residency for decades, using mail forwarding services and returning briefly each year to renew licenses. The state doesn't require you to own property or spend a minimum number of days there annually. However, if your goal is eventually settling permanently somewhere, you'd probably want to establish residency in that future state once you purchase property there. SD domicile works best for people who genuinely want to maintain mobility rather than as a temporary tax avoidance strategy.

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Tony Brooks

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As someone who's dealt with property tax issues for years, I want to emphasize the importance of verifying any strategy with qualified professionals before implementation. While many of the suggestions here are legitimate, the devil is really in the details when it comes to tax law. A few additional points to consider: 1) **Agricultural exemptions** can be excellent but often require genuine agricultural activity - not just owning rural land. Most states require proof of income from farming/ranching or specific land management practices. 2) **Land trusts** are another option worth exploring. Some states allow you to place property in an irrevocable trust that can reduce property tax assessments, though you do give up certain ownership rights. 3) **Tax lien investing** - while not eliminating your own property taxes, you can actually profit from others' unpaid property taxes by purchasing tax liens in states that offer this investment vehicle. 4) **Religious/charitable exemptions** - if you're operating a legitimate religious organization or charity from your property, portions may qualify for exemption in many jurisdictions. Whatever route you choose, make sure you understand the long-term implications. Some strategies that eliminate property taxes may create other tax obligations or limit your property rights in ways that could be costly down the road. Always consult with both a tax attorney and CPA familiar with your specific state and local laws before making major decisions.

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This is incredibly helpful advice, Tony! The point about agricultural exemptions requiring genuine agricultural activity is something I definitely needed to understand better. I've been looking at some rural properties and assumed that just owning farmland would automatically qualify, but it sounds like I'd need to actually operate a farm or ranch to claim the exemption. Do you happen to know what constitutes "genuine agricultural activity" in most states? Is there typically a minimum income requirement, or would something like a small market garden or keeping a few livestock be sufficient? I'm trying to understand if this would be feasible for someone who wants to be largely self-sufficient but isn't planning to run a full commercial farming operation. Also, your mention of land trusts is intriguing. When you say you "give up certain ownership rights," what specific rights are typically affected? I'm wondering if this would impact things like the ability to sell the property or make major improvements.

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Oliver Weber

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Anyone know which tax software handles the Lifetime Learning Credit the best? I tried using the free version of TaxAct last year and it kept trying to upgrade me to the paid version when I mentioned education expenses.

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I used FreeTaxUSA last year and it handled my Lifetime Learning Credit perfectly fine without trying to upsell me. They have a totally free federal filing option that includes education credits. You only pay if you want state filing.

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Zoe Papadakis

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Great question! This confusion comes up a lot, and I'm glad you asked because many people miss out on valuable education credits due to this misconception. Yes, you can absolutely claim the Lifetime Learning Credit while taking the standard deduction! These are two completely different parts of your tax return that don't interfere with each other at all. Here's the breakdown: - Standard deduction vs. itemizing affects how your taxable income is calculated - Tax credits like the Lifetime Learning Credit reduce your actual tax owed after your taxable income has already been determined So the process is: Calculate your taxable income (using standard deduction) → Calculate your tax owed → Apply credits like Lifetime Learning Credit to reduce that tax bill. With your $3,200 in tuition expenses, you could potentially get a credit of up to $640 (20% of qualified expenses, up to $2,000 maximum credit). Definitely don't skip claiming this! You'll need Form 8863 when you file. Your brother-in-law was probably thinking of certain itemized deductions, but education credits work differently. Take advantage of both the standard deduction AND your education credit!

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I'm so glad you asked this question! I literally went through the exact same confusion when I first looked at my transcript a few months ago. Saw those minus signs and immediately thought "oh no, did I mess something up??" 😰 But yeah, everyone here is absolutely right - the IRS uses this totally backwards accounting system where negative amounts actually mean GOOD news for you! Your -$4,322 is definitely your refund matching what TurboTax calculated. It's honestly wild that the IRS hasn't figured out that maybe normal people don't think in accounting terms and those minus signs are super confusing. Like would it kill them to just write "REFUND AMOUNT" instead of making us all panic? But congrats on getting money back - that's always a nice feeling! 💰

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This whole thread has been such a lifesaver! I'm literally bookmarking this because I know I'll probably forget and have the same panic attack next year 😅 It's honestly mind-blowing that the IRS can't just add a simple legend or explanation somewhere on the transcript that says "negative = refund, positive = amount owed" - like how is that not standard by now?? But I'm so grateful everyone shared their experiences because it makes me feel way less crazy for having that initial freak out moment. The IRS really needs to hire some user experience designers or something because this system is clearly broken when EVERYONE has the exact same confusion!

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Ryan Vasquez

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I literally just had this same panic attack yesterday! 😅 Opened my transcript, saw -$2,134 and my first thought was "oh no, what did I do wrong on my taxes??" I actually took a screenshot and sent it to my sister asking if I was reading it right because those minus signs made me think I somehow owed money instead of getting a refund! It's honestly ridiculous that the IRS uses this backwards accounting system without any explanation whatsoever. Like seriously, would it kill them to put a little note somewhere that says "negative amounts = refunds" so we don't all have mini heart attacks? But yeah, your -$4,322 is definitely your refund - same amount TurboTax calculated, just displayed in the most confusing way possible. Welcome to the club of people who survived their first transcript panic! 😂

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