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Most people forget you can also get free tax help through VITA (Volunteer Income Tax Assistance) if you make under $60k. They can help with basic investment forms like 1099-DIV. Just google "VITA tax help near me" to find locations. I used them last year and they were great!

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VITA volunteers aren't always trained on investment income though. I tried using them 2 years ago and the volunteer told me they couldn't help with my stock sales, only with W-2 income. Might depend on which location you go to and who's volunteering that day.

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Samantha Hall

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Don't stress too much about the 1099-DIV - it's actually pretty straightforward once you understand the basics! The key thing to remember is that TurboTax will walk you through each box step by step. You'll enter the amounts from Box 1a (total ordinary dividends) and Box 1b (qualified dividends), and the software automatically calculates the tax differences for you. One tip: keep your 1099-DIV with your other tax documents for next year. As your dividend income grows, you might want to consider making quarterly estimated tax payments if it becomes substantial, but at $780 you're nowhere near that point yet. Also, since you're using Fidelity, they usually have good tax resources on their website that explain dividend taxation in plain English if you want to learn more about how this all works for future years.

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This is really helpful advice! I'm also pretty new to investing and have been wondering about the quarterly estimated tax payments you mentioned. At what point does dividend income typically become large enough that you need to start making those payments? Is there a specific dollar threshold or percentage of your total income where it makes sense to switch from just paying when you file to making quarterly payments?

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Freya Larsen

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Quick tip that helped me with a similar Depop situation: take photos of your closet/items before selling them as additional documentation. The IRS knows you're not running a business if you're just selling random personal items from your closet at a loss.

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That's such a smart idea! I still have some items I haven't shipped yet, so I'll definitely take photos. Do you know if there's any specific way I should document the original purchase prices? I was thinking of making a spreadsheet with my best estimate for each item.

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Freya Larsen

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A spreadsheet is perfect! I created one with columns for: item description, estimated purchase date, estimated original price, selling price, and platform fees. This clearly showed everything was sold at a loss. For items where I couldn't remember the exact price, I looked up similar items online from the same brand to get a reasonable estimate. The key is being able to show you made a good faith effort to accurately report everything. Adding photos of the items from your closet just provides extra evidence these were personal items, not inventory purchased for resale.

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Jamal Harris

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This thread has been incredibly helpful! I'm dealing with a similar situation where I sold some old designer bags and shoes on various platforms and received multiple 1099-Ks. One thing I want to add for anyone in this situation - don't panic when you see that 1099-K amount! It looks scary but remember it's just reporting gross payments, not your actual taxable income. Like everyone mentioned, if you sold personal items for less than you paid, you're not making taxable profit. I ended up creating a detailed spreadsheet tracking each sale, and even though I estimated most of my original costs (who keeps receipts for shoes from 2018?), I was conservative with my estimates. For example, if I thought I paid around $150-200 for something, I'd estimate $150 to be safe. The key is being able to show these were clearly personal items from your closet, not business inventory. Screenshots of your listings showing the items as "from my closet" or "gently worn" can help demonstrate this too.

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NightOwl42

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This is exactly the reassurance I needed! I've been losing sleep over my 1099-K since it arrived. Your point about being conservative with estimates is really smart - I was worried about underestimating, but you're right that it's better to be safe than sorry. I love the idea about using screenshots of the listings showing "from my closet" language. I actually wrote things like "cleaning out my wardrobe" and "barely worn" in most of my descriptions, so those should help show intent. Did you have any issues during filing, or did everything go smoothly once you had your documentation organized? Also wondering - did you report each platform separately or combine everything? I have 1099-Ks from both Depop and Poshmark.

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How to properly calculate cost basis for ESPP stocks and RSUs when transferring brokerages?

I'm completely lost when it comes to understanding cost basis for my company stock options. I've owned a mix of ESPP stocks and RSUs from my previous employer for about 6 years now. I no longer work at the company. Currently, these shares are sitting in an Etrade ESPP stock plan account that's linked to my former employer. I recently discovered they're charging me $25 for each transaction I make on these stocks - even selling a single share costs me $25! I learned I could transfer these stocks to a regular brokerage account with no trading commissions, so I called Etrade to get this process started. Here's where it gets confusing. The Etrade rep warned me that the ESPP account provides important tax information that the regular account doesn't. They explained that when selling ESPP stocks or RSUs, it's not like selling regular stocks - you need to account for the "estimated cost basis" in addition to the sale price and gain/loss. Apparently, the ESPP account automatically calculates all this and provides tax documents, which is what I'm paying for with those high fees. I'm willing to track this information myself to avoid the fees, but I spent over an hour on the phone and still have no idea what I actually need to calculate or how to determine this "estimated cost basis." When I asked how it's calculated, they said it varies by company policies and is too complex to explain. They mentioned it somehow factors in my income, but didn't explain how. I really want to move away from this high-commission account, but I'm concerned about this cost basis issue. What exactly is this estimated cost basis for ESPP and RSUs? How do I calculate it myself? Are there resources where I can learn about this? Is this something I can reasonably handle myself, or should I just keep paying the fees?

CosmicCaptain

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Has anyone used TurboTax for reporting ESPP and RSU sales? I'm wondering if they have any built-in tools for calculating the correct cost basis. I transferred my shares to Fidelity last year and now I'm worried I might mess up my taxes.

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Malik Johnson

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TurboTax Premium has a section specifically for ESPPs and RSUs. It asks about your purchase date, purchase price, offering date (for ESPP), FMV at time of purchase, and sale details. It then calculates everything correctly, including whether you have a qualifying disposition. The key is having all your original documentation from Etrade before you start. Last year I had to pause my tax prep and call my former employer's stock admin team to get some missing information about my ESPP offering periods.

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Ezra Bates

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One thing I'd add to all the great advice here - make sure you understand the "look-back" provision that many ESPPs have. This can significantly affect your cost basis calculation and whether you have a qualifying disposition. Many ESPPs allow you to purchase shares at a discount based on the LOWER of either the stock price at the beginning of the offering period OR the stock price at the end of the offering period. If your plan had this feature, your actual purchase price might be different than what you think, and this affects both your cost basis and the amount of discount that gets taxed as ordinary income. I learned this the hard way when I sold some old ESPP shares and discovered my cost basis was actually lower than I calculated because of the look-back provision. Check your original ESPP plan documents or contact your former employer's benefits team to confirm if your plan had this feature. Also, don't forget that some brokerages will automatically apply incorrect cost basis adjustments when you transfer ESPP shares. Make sure to review and correct these before you sell, or you might end up paying taxes on money you've already been taxed on.

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Beth Ford

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This is such an important point about the look-back provision! I had no idea this even existed and I've been holding ESPP shares for 3 years. How do I find out if my company's plan had this feature? My former employer was acquired last year, so I'm not sure who would even have access to the original plan documents anymore. Also, when you mention brokerages applying incorrect cost basis adjustments during transfers - is this something I should proactively check, or will it be obvious when I look at my account? I'm planning to transfer my shares from Etrade to Vanguard next month and want to make sure I don't miss this.

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I just take a picture of mixed receipts immediately and mark them up digitally using my phone's markup tools. Circle business items in red, add up the subtotal right on the image, and calculate the proportional tax. Then save to a tax folder in my cloud storage. My accountant said the IRS doesn't require original paper receipts anymore - digital copies are acceptable as long as they're legible and you can prove the expense was for business.

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Great question! I've been dealing with this exact same issue as a freelance consultant. Here's what I've learned works best: For mixed receipts, definitely keep them - just be methodical about marking them up. I use a simple system: I circle all business items in blue ink and write "BIZ" next to each one, then total up just those items at the bottom of the receipt. This makes it crystal clear what portion was for business. For the sales tax calculation, the proportional method is totally acceptable. If your business items were $30 out of a $60 total purchase, then you can claim 50% of the sales tax ($6.43 out of your $12.85 example). The IRS just wants to see that you have a reasonable, consistent method. One tip that's saved me time: I do this markup immediately while I'm still in the parking lot or as soon as I get home. Trying to remember what was business vs personal weeks later is nearly impossible, especially for generic items like batteries or folders. Your spreadsheet approach sounds solid - just make sure you're only entering the business portion of each receipt, including the calculated business portion of sales tax. Keep those marked-up receipts organized by month in case you need them later!

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This is super helpful! I love the blue ink "BIZ" system - that's way clearer than my current highlighting method. One question though: do you think it matters if I use different colored pens for different months or years? Like blue for 2024, red for 2025? Or is consistency within each receipt more important than having a color coding system across time? Also, thanks for the parking lot tip! I've definitely had those moments where I'm staring at a receipt two weeks later wondering if the USB cable was for my computer or my kid's tablet.

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How to Claim Premium Tax Credit & Self-Employed Health Insurance Deduction Together

My family's in a weird tax situation and I'm hoping someone here understands this specific issue. My husband runs his own business and is currently the only income earner for our household of 5. We bought health insurance through the marketplace for 2024 without taking the advance premium tax credit, and we're planning to take the self-employed health insurance deduction. Here's where it gets complicated: After taking the self-employed health insurance deduction, our MAGI drops below the 400% threshold, which means we qualify for the premium tax credit. But if we take the full PTC, that would reduce our self-employed health insurance deduction and push our MAGI back up, potentially making us ineligible for the PTC again. I've been reading IRS publication 974 which says: "If you are eligible for both a self-employed health insurance deduction and the PTC for the same premiums, you may use any computation method that results in reporting amounts that satisfy the rules for both the deduction and PTC, as long as the sum of the deduction claimed for the premiums and the PTC computed, taking the deduction into account, is less than or equal to the enrollment premiums." So my question is: Are we required to take the MAXIMUM premium tax credit amount? Or can we choose to take a smaller PTC to maintain enough of a deduction to stay eligible? Could we submit a tax return where the PTC we claim (form 8962, line 24) is different than the calculated annual PTC (line 11 column e)? Or could we just claim the PTC for some months but not others, even though our 1095-A shows coverage for all of us for the entire year? We did hire a tax preparer, but they totally missed that our second-lowest cost silver plan was missing because we didn't take the advance PTC, so they filed without even considering we could take the PTC. So I'm not sure they really understand this circular reference problem.

Amina Sy

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Has anyone here actually gone through an audit with this kind of partial PTC claim? I'm concerned about taking less than the maximum amount I'm eligible for, even though it seems allowed by the rules.

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I had a correspondence audit last year where they questioned my PTC calculation. I submitted my worksheet showing how I determined the partial PTC amount to maintain eligibility, along with the quote from Pub 974. They accepted it without further questions. They seemed familiar with the circular reference issue.

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Chloe Taylor

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This is such a complex situation that many taxpayers face! I went through something similar last year with my consulting business. One thing that helped me was creating a simple spreadsheet to model different scenarios. Here's what I learned from working through this: The key is finding that "Goldilocks zone" where your PTC claim is just right - not so high that it pushes your MAGI over the 400% threshold, but high enough to give you meaningful tax savings. I ended up claiming about 75% of my maximum eligible PTC, which kept my MAGI at around 395% of the federal poverty level. This allowed me to maintain both the self-employed health insurance deduction and a substantial premium tax credit. One tip: when you're doing the calculations, remember that the self-employed health insurance deduction goes on Schedule 1, which directly reduces your AGI, while the PTC is a refundable credit. So you want to optimize for the combination that gives you the lowest overall tax liability. The IRS really does understand this circular reference problem - it's not some obscure loophole. Publication 974 specifically addresses it because so many self-employed people with marketplace coverage face this exact scenario. Don't let your tax preparer's confusion discourage you from pursuing this legitimate approach!

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Noah Irving

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This is really helpful! I'm in a similar situation as a freelancer and was getting overwhelmed by all the calculations. Your "Goldilocks zone" analogy makes it much clearer - finding that sweet spot where everything works together. Quick question though - when you say you claimed 75% of your maximum eligible PTC, how did you determine that specific percentage? Did you just try different amounts until you found one that kept your MAGI under 400%, or is there a more systematic way to find the optimal point? Also, did you have any issues with your tax software handling this approach, or did you have to override some of the automatic calculations?

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