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Just wanted to mention that if you're overwhelmed by the DIY approach, look into the Volunteer Income Tax Assistance (VITA) program or Tax-Aide through AARP. They sometimes help with back tax returns, not just current year filing. Also, the IRS has a formal program called "First Time Penalty Abatement" where they'll often waive penalties for the first time you've had filing/payment issues if you've otherwise been compliant in prior years. Definitely worth asking about if this is your first time having tax troubles.

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Joy Olmedo

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I used VITA last year for my back taxes and they were amazing! Just want to clarify though that most VITA sites only handle relatively simple tax returns and many have income limits (usually around $60k). Also, not all VITA sites handle prior year returns - you need to call ahead and ask specifically.

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One thing I haven't seen mentioned yet is the importance of filing in the correct order - you'll want to file your oldest returns first and work your way forward to the most recent year. This is because each year's tax calculation can be affected by carryforwards from previous years (like capital losses, charitable contributions, or net operating losses). Also, if you had any estimated tax payments or extensions filed for any of those years, make sure to include that information on your returns. The IRS already has records of any payments you made, so you want to make sure you get credit for them. Another tip: when you do file all these back returns, send them via certified mail with return receipt requested. This gives you proof of when the IRS received them, which can be important for penalty calculations and establishing your "good faith" effort to come into compliance voluntarily. The process feels overwhelming now, but once you get started and have a system in place, it goes faster than you'd expect. You've got this!

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This is incredibly helpful advice about filing in chronological order - I hadn't thought about how carryforwards could affect the calculations! Quick question though: if I'm missing some documents for the earliest years but have everything for more recent years, should I wait to file anything until I have all the old documents? Or can I start with what I have and amend the older returns later if needed? Also, the certified mail tip is brilliant. I'm definitely paranoid about the IRS claiming they never received something, especially given how long I've already let this drag on. Thanks for taking the time to share all this detail - it's exactly the kind of practical advice I needed to hear!

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Does anyone know if employer-paid tuition counts toward the Lifetime Learning Credit or American Opportunity Credit? I'm taking MBA classes that my employer pays for directly (about $4,200 this year), but I also paid about $1,000 out of pocket for books and some fees. Can I claim any education credits for the portion I paid myself?

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NeonNova

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You can't claim education credits on the portion your employer paid tax-free, but you CAN claim credits for the qualified expenses you paid out of pocket (like your books and fees). Just make sure not to double-dip by claiming credits for expenses that were covered by tax-free employer assistance.

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Thanks, that's exactly what I needed to know! So I'll just claim the $1,000 I paid personally for the education credits and ignore the $4,200 my employer paid directly. Makes sense that you can't get both tax-free employer assistance and tax credits for the same expenses.

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I went through this exact situation last year and it was so confusing at first! The key thing that helped me understand it was realizing that the 1098-T is just the school's way of reporting what they received - it doesn't automatically mean you owe taxes on it. Since your employer paid $4,800 directly and that's under the $5,250 annual limit for tax-free education assistance, you should be fine. The most important step is checking your W-2 to confirm your employer properly excluded this amount from your taxable wages in Box 1. One thing I learned the hard way - keep documentation from your employer about their education assistance program. If the IRS ever questions it, you'll want proof that this was provided under a qualified educational assistance program rather than just additional compensation. Most HR departments can provide a letter or policy document that explains how their education benefits work. Also, don't stress too much about the 1098-T showing the full amount in Box 1. Schools are required to report all payments they receive, regardless of the source or tax treatment. As long as your employer handled it correctly on your W-2, you can essentially ignore that 1098-T for tax purposes.

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RaΓΊl Mora

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This is really helpful advice! I'm actually in a very similar situation - my company paid about $3,800 directly to my school this year. I just checked my W-2 and thankfully my employer did exclude it from Box 1, so it looks like they handled it correctly. The documentation tip is gold - I never thought about getting something in writing from HR about their education assistance program. I'm definitely going to request that before I file my taxes, just to have it on record. Better safe than sorry when it comes to the IRS! One quick question - did you have to do anything special on your actual tax return to indicate that the 1098-T amount was covered by employer assistance, or did you literally just ignore it completely when filing?

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Amara Torres

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This entire discussion has been absolutely invaluable! I'm someone who typically overthinks every detail when it comes to taxes, and this thread has provided such clear, consistent guidance from so many different perspectives. What really convinced me was hearing from actual tax professionals - CPAs, EAs, tax attorneys, and VITA volunteers - all saying the same thing: use "0" instead of leaving fields blank. The technical explanation about OCR systems and XML processing was particularly enlightening, and the real-world stories about people getting CP2000 notices for leaving blanks really drove home why this matters. I'm now confidently going through my return and putting zeros in all applicable fields. It's such a simple fix that can prevent major headaches down the road. Thank you to everyone who shared their expertise - this community is incredible for helping nervous taxpayers like me navigate these details with confidence!

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Shelby Bauman

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I'm so glad this discussion has been helpful for you! As someone who's also new to filing taxes independently, I completely understand that tendency to overthink every little detail. Reading through all these professional perspectives and real-world examples has been incredibly reassuring. The consistency of the advice from CPAs, EAs, tax attorneys, and volunteers really shows this isn't just opinion - it's established best practice. I especially appreciated how everyone explained not just the "what" but the "why" behind using zeros instead of blanks. It makes the whole process feel less mysterious when you understand how the IRS systems actually work. Thanks for adding your voice to this thread - it's encouraging to see other newcomers feeling more confident about tackling their returns after learning from this community!

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Payton Black

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This has been such an educational thread to read through! As someone who just graduated college and is filing taxes independently for the first time, I was having the exact same anxiety about zeros vs. blanks. Reading all the professional advice from CPAs, EAs, and tax attorneys, plus the real-world experiences from people who've dealt with IRS correspondence over blank fields, has completely convinced me that zeros are the way to go. The technical explanation about OCR systems and processing workflows was particularly eye-opening - it really helps to understand the "why" behind the guidance. I'm definitely going to follow the systematic approach several people mentioned: going through my entire Form 1040 and putting "0" in every field that applies to my situation but has zero amount. Better to spend a few extra minutes now than deal with potential processing delays or correspondence later! Thank you to everyone who shared their expertise and experiences. This community has been incredibly helpful for easing first-time filer anxiety!

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Mateo Sanchez

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Welcome to the independent tax filing world! Your approach of researching thoroughly before filing shows you're already on the right track. As someone who went through that same first-time filer anxiety a few years ago, I can tell you that taking the time to understand these details upfront really pays off in peace of mind later. The systematic approach you mentioned - going through the entire Form 1040 and adding zeros to applicable fields - is exactly what I did on my first return and it made the whole process feel much more manageable. You're definitely making the smart choice by learning from everyone's experiences here rather than having to figure it out the hard way. Good luck with your first independent filing!

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Aisha Khan

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As a tax professional who's worked with several SCIN implementations, I want to address some of the excellent questions raised by @Morgan Washington and @NightOwl42. Regarding note terms for someone in their early 60s: The "sweet spot" typically falls between 10-15 years. Shorter terms (5-7 years) often don't provide sufficient estate planning benefits to justify the complexity, while longer terms (20+ years) can require premiums so high they make the transaction uneconomical. At age 62, a 12-year term often provides a good balance between meaningful wealth transfer potential and manageable premium requirements. On minimum estate thresholds: In my experience, SCINs generally don't make economic sense for estates under $5-7 million. The professional fees, ongoing complexity, and opportunity costs need to be weighed against simpler alternatives like annual gifting or basic trusts. For larger estates ($10M+), the potential estate tax savings often justify the complexity and costs involved. One additional consideration I haven't seen mentioned: the impact of the 2025 estate tax exemption sunset. With exemptions potentially dropping significantly in 2026, there's been increased interest in SCINs as wealth transfer vehicles, but this also means more IRS scrutiny is likely coming. For those moving forward with SCINs, I strongly recommend stress-testing your premium calculations under different interest rate and health scenarios to ensure the structure remains viable even if circumstances change.

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Thank you for this practical breakdown, @Aisha Khan! Your insights about the 10-15 year sweet spot and minimum estate thresholds are really helpful for understanding when SCINs make sense. I'm particularly interested in your mention of the 2025 estate tax exemption sunset. For someone just starting to explore SCINs now, would you recommend accelerating the timeline to implement before 2026, or is that creating unnecessary pressure that might lead to mistakes in the premium calculation or documentation process? Also, when you mention stress-testing premium calculations under different scenarios, are you referring to modeling what happens if interest rates change significantly during the note term, or if the seller's health status changes? I'm trying to understand what variables are most important to test for robustness. As someone new to this area, I'm also curious - have you seen increased IRS examination rates for SCINs implemented in 2023-2024, given the anticipated increase in activity before the exemption changes?

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As someone who recently completed a SCIN implementation for my manufacturing business, I wanted to share a few practical insights that might help others navigating this complex process. The premium calculation ended up being more art than science, despite all the technical requirements. We used a 14-year term for $12M in business interests, with my age (64) and relatively good health factoring into a 25% interest rate premium above AFR. Our actuary's report was crucial - it included sensitivity analyses showing how different mortality assumptions affected the premium, which gave us confidence we were in the right ballpark. One thing I wish I'd known earlier: the business valuation timing matters enormously. We initially got our appraisal in March, but by the time we were ready to execute in June, market conditions had shifted enough that we needed an updated valuation. This delayed our closing by three weeks, but our attorney insisted it was necessary for defensibility. The documentation process was more extensive than I expected. Beyond the basic SCIN agreement, we maintained detailed files on: premium calculation methodology, health assessments, comparable market transactions, and monthly tracking of Section 7520 rates during our planning period. Our attorney said this level of documentation has become essential given increased IRS scrutiny. For anyone considering this strategy, I'd recommend starting the professional team assembly at least 4-6 months before you want to execute. The coordination between attorneys, actuaries, and appraisers takes time, and rushing the process increases the risk of mistakes that could be costly later.

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Mei Wong

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Thank you for sharing your real-world experience with the SCIN implementation, @Oliver Schmidt! Your point about the business valuation timing is particularly valuable - I hadn't considered how market shifts during the planning period could affect the underlying asset values and potentially impact the premium calculation validity. A couple of follow-up questions based on your experience: 1) When you mention the 25% interest rate premium above AFR, how did your actuary justify that specific percentage? Was it primarily driven by your age/health profile, or were there other risk factors that influenced that calculation? 2) Did you encounter any unexpected challenges with the monthly Section 7520 rate tracking, or was that relatively straightforward to manage? Your recommendation about starting the team assembly 4-6 months early is really practical advice. Given all the coordination required between different professionals, I can see how trying to rush this process could easily lead to errors that might not surface until an IRS examination years later. For someone just beginning to explore SCINs, would you recommend engaging all the professionals (attorney, actuary, appraiser) simultaneously at the start, or is there a preferred sequence that makes the process more efficient?

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Yara Sabbagh

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@Oliver Schmidt, your real-world experience is incredibly valuable! I'm particularly interested in your point about the business valuation timing. Did you find that the market shift between March and June significantly affected your premium calculation, or was it more about maintaining defensibility with current valuations? Also, I'm curious about the "art vs. science" comment regarding premium calculations. Even with all the technical requirements and actuarial analysis, how much subjective judgment was involved in arriving at that 25% premium? Did your team consider multiple premium scenarios, or was there a fairly clear "right answer" once you ran the numbers? Your documentation advice resonates with what others have mentioned about IRS scrutiny. The monthly Section 7520 rate tracking sounds particularly meticulous - was this something your attorney recommended from the start, or did you add this level of detail based on feedback during the process? Finally, for the 4-6 month timeline you recommend, did you find that certain steps were more time-sensitive than others, or was it more about allowing buffer time for the overall coordination between professionals?

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Welcome to the world of self-employment taxes! As a fellow young entrepreneur who started tutoring in college, I totally get the confusion. Here are some key points that might help: First, you're right that you need to report income over $400, and yes, you'll owe self-employment tax on your net profit (around 15.3%). The IRS can definitely track your income through payment processors like Venmo and PayPal - they report transactions over certain thresholds. Regarding your college expenses: unfortunately, you can't deduct your general education as a business expense just because it helps your tutoring. The IRS distinguishes between education that maintains/improves existing business skills versus education that qualifies you for a new profession. Since you're pursuing a degree, that typically falls into the latter category. However, you CAN deduct legitimate business expenses like: - Mileage to/from tutoring sessions (keep a detailed log!) - Tutoring materials, books, supplies - Business portion of phone/internet if used for tutoring - Any software or apps specifically for your tutoring business My advice: open a separate account for tutoring income ASAP and track every business expense. Even if your net profit is small after legitimate deductions, you'll still likely owe some self-employment tax. But proper record-keeping will ensure you're only paying what you actually owe! Also consider setting aside 25-30% of each payment for taxes so you're not caught off guard at filing time.

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Quinn Herbert

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This is such solid advice! I'm just starting out with tutoring too and had no idea about the separate account thing. Quick question - when you say "business portion" of phone/internet, how do you actually calculate that percentage? Like if I use my phone 30% for tutoring stuff, can I just deduct 30% of my monthly bill?

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Malik Johnson

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Yes, that's exactly right! If you use your phone 30% for tutoring business, you can deduct 30% of your monthly phone bill. The key is being able to substantiate that percentage if the IRS ever asks. I keep a simple log for a few weeks each year tracking my business vs personal usage - noting tutoring calls, business texts, using maps to drive to students, etc. You don't need to track every single minute forever, but having some documentation of your typical usage pattern is smart. Same concept applies to internet - if you're doing online tutoring, researching materials for students, or handling business communications, track that time and calculate a reasonable business percentage. Just make sure your percentages are realistic and you can justify them with actual usage patterns!

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NeonNomad

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Great question, Diego! I went through the exact same confusion when I started my side business. A few key points that might help clarify things: First, regarding your gift money vs tutoring income - the IRS actually has ways to track this through 1099 forms from payment processors and bank deposit patterns. It's much better to be transparent and keep separate records than to try to blur the lines. Second, I see you're thinking about deducting all your education costs, but unfortunately that won't work. Your college degree program prepares you for a new career/profession, so the IRS considers that personal education rather than business training. However, you CAN deduct specific tutoring-related expenses like materials you create for students, supplies, and yes - mileage when driving to meet students (keep that detailed log!). One thing that really helped me was calculating my actual tax burden early on. With $840 in income, after legitimate business deductions, you're probably looking at owing around $120-180 in self-employment tax (15.3% on net profit). Not huge, but definitely something to plan for. My biggest recommendation: start separating your business and personal finances NOW. Open a dedicated account for tutoring income and track every business expense. It makes tax time so much easier and shows the IRS you're running a legitimate business rather than just mixing everything together. Also, consider setting aside about 25% of each tutoring payment for taxes so you're not scrambling come filing time!

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Emma Bianchi

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This is really helpful perspective! I'm curious about one thing though - you mentioned calculating the actual tax burden early on. Do you have any recommendations for tools or methods to estimate what you'll owe throughout the year? I feel like I'm flying blind trying to figure out if I should be making quarterly payments or if I can just handle everything at the end of the year. Also, when you say "legitimate business expenses" - I assume things like gas to drive to students counts, but what about if I grab coffee while I'm out tutoring? Or if I buy a new backpack that I use mostly for carrying tutoring materials? Where's the line between personal and business expenses?

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