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Ella Lewis

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Omar, you're absolutely right to be concerned about this! I went through the same confusion last year when I started getting paid through Zelle for my consulting work. The key thing to understand is that while Zelle doesn't send 1099-K forms like PayPal or Venmo, ALL income is still taxable regardless of how you receive it. Think of it this way - if someone paid you $25,000 in cash, you'd still owe taxes on it even though there's no paper trail, right? For your $25,000 in annual Zelle payments, you'll need to report this as business income on Schedule C of your tax return. Make sure you're also tracking any business expenses you can deduct - things like software subscriptions, equipment, home office expenses, etc. These deductions can significantly reduce your tax liability. My advice: Start keeping meticulous records NOW. Create a simple spreadsheet with columns for date, client name, amount, and description of work. Also save screenshots of your Zelle transactions as backup documentation. The IRS may not get automatic reports from Zelle, but if you're ever audited, they'll definitely want to see proof of your income and expenses. Don't risk not reporting it - the penalties and interest for unreported income are way worse than just paying the taxes upfront. Better to be safe and compliant!

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Payton Black

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Thanks for this detailed breakdown! I'm in a similar situation with my freelance work and have been using a basic spreadsheet, but I'm wondering about quarterly estimated tax payments. Since Zelle doesn't withhold taxes like a regular employer would, am I supposed to be making quarterly payments to the IRS? With $25K annually, that seems like it would put me in the range where I'd owe a significant amount at tax time if I'm not paying throughout the year.

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@Payton Black You re'absolutely right to think about quarterly payments! Yes, if you expect to owe $1,000 or more in taxes when you file, the IRS generally requires quarterly estimated tax payments. With $25K in freelance income, you ll'likely hit that threshold unless you have significant business deductions. The quarterly due dates are January 15, April 15, June 15, and September 15. You can calculate your estimated payments using Form 1040ES, but a rough rule of thumb is to set aside about 25-30% of your net profit for taxes income (taxes plus self-employment tax .)Since you re'self-employed, you ll'also owe self-employment tax Social (Security and Medicare on) top of regular income tax, which is about 15.3% of your net earnings. This is something a lot of freelancers forget about until tax time! If you haven t'been making quarterly payments this year, you can start now and just pay what you owe for the remaining quarters. The IRS won t'penalize you for late quarterly payments as long as you pay the full amount owed when you file your annual return, though you might owe a small underpayment penalty.

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Quinn Herbert

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The confusion around Zelle and tax reporting is totally understandable, Omar! I went through this exact same worry when I started my freelance photography business. Here's the bottom line: Zelle's exemption from 1099-K reporting requirements doesn't exempt YOU from reporting the income. The $25,000 you're making annually absolutely needs to be reported on Schedule C as self-employment income, and you'll owe both regular income tax AND self-employment tax on it (about 15.3% for Social Security/Medicare). Since you mentioned your record-keeping hasn't been meticulous, I'd strongly recommend going back through your bank statements and Zelle transaction history to create a complete record of all payments received. The IRS can easily spot unreported income during an audit by comparing your bank deposits to your reported income, even without 1099 forms. Also, don't forget about quarterly estimated tax payments! With $25K in annual income, you're likely going to owe more than $1,000 when you file, which means the IRS expects you to make quarterly payments throughout the year rather than paying it all at once in April. You can use Form 1040ES to calculate what you should be paying each quarter. The good news is that as a freelancer, you can deduct legitimate business expenses like software, equipment, home office costs, etc. to reduce your taxable income. Just make sure you keep receipts and documentation for everything you claim.

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I went through this exact same process about 6 months ago and totally understand the anxiety! The good news is that it's really not as scary as it seems at first. I called the number on my 5747C letter and yes, the wait time was brutal - about 2.5 hours on hold - but once I got through, the actual verification was pretty straightforward. The agent asked me to confirm basic info like my address, filing status, and some line items from my current and prior year returns. They also asked about my employer and a few specific deductions I claimed. The whole conversation took maybe 20 minutes once I was connected. My refund was issued exactly 6 weeks after the call, which was actually faster than they initially told me to expect. Just make sure you have your tax documents handy when you call - both this year's and last year's returns. The IRS agent was actually pretty helpful and explained that my return was flagged because I had moved states and changed jobs, which created an unusual pattern in their system. Don't stress too much about it - it's really just a verification process to make sure you are who you say you are!

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Thanks for sharing your experience! It's really helpful to hear from someone who's been through this. The 2.5 hour wait time sounds absolutely brutal though - I'm dreading that part. Did you have to stay on the line the whole time or were you able to use speakerphone and do other things while waiting? I'm trying to figure out the best strategy for getting through without losing my mind on hold.

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I definitely used speakerphone and did household chores while waiting! Just make sure your phone is fully charged or plugged in. I also had all my documents organized beforehand so I wouldn't be scrambling when they finally picked up. The hold music is repetitive but at least you know you're still in the queue. Pro tip: call first thing in the morning (like 7 AM sharp when they open) - I've heard the wait times are shorter then, though I called mid-afternoon and still got through eventually.

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I got a 5747C letter about three weeks ago and finally made it through the verification process yesterday. I wanted to share what worked for me since I know how stressful this can be! I tried calling multiple times but kept getting disconnected or couldn't get through at all. Finally decided to schedule an in-person appointment at my local Taxpayer Assistance Center, which was honestly the best decision. The appointment was scheduled for about 10 days out, but the actual process was so much smoother than trying to call. The IRS representative was really professional and walked me through everything step by step. She explained that my letter was triggered because I had claimed the Earned Income Tax Credit for the first time this year after getting a new job. Apparently that's a common trigger for their fraud detection system. I brought my driver's license, Social Security card, current year tax return, last year's return, and all my W-2s. The whole appointment took about 25 minutes, and she was able to verify my identity on the spot. She told me to expect my refund within 6-9 weeks, but honestly just having it resolved felt like a huge weight off my shoulders. If you're struggling with the phone lines, I'd really recommend trying the in-person route if you have a Taxpayer Assistance Center nearby. Much less frustrating than sitting on hold for hours!

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This is really helpful advice! I'm dealing with a 5747C letter right now and have been dreading the phone calls after hearing about those crazy wait times. I didn't even realize you could schedule in-person appointments - that sounds so much better than being stuck on hold for hours. How did you go about scheduling the appointment? Is there a specific website or do you have to call a different number? And did they give you a list of what documents to bring, or did you just bring everything you thought might be relevant? I want to make sure I'm fully prepared so I don't have to make a second trip.

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Thank you for sharing this detailed comparison! As someone who's been hesitant to switch from TurboTax after using it for so many years, your experience is exactly what I needed to hear. The $173 price difference for identical results is just shocking - that's real money that could go toward building an emergency fund or paying down debt instead. I'm particularly interested in your plan to test multiple platforms next year. Would you consider including user experience factors like time spent, ease of navigation, and quality of explanations in your comparison? Sometimes the cheaper option can end up costing more in time and frustration, so it would be helpful to know if FreeTaxUSA requires significantly more tax knowledge to navigate effectively. Also, did you notice any differences in the audit support or guarantees offered by each platform? That's one area where I've always felt more comfortable with TurboTax, but I'm curious if it's more marketing than substance.

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Wesley Hallow

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Great points about user experience and audit support! I'm definitely planning to include those factors in my comparison next year. From my initial experience with FreeTaxUSA, I'd say it does require a bit more tax knowledge - TurboTax really holds your hand through every step with plain-language explanations, while FreeTaxUSA assumes you understand basic tax concepts. Regarding audit support, TurboTax offers their "Audit Support" service where they'll represent you, but it's actually a separate paid add-on that costs extra. FreeTaxUSA provides audit correspondence support (they'll help you respond to IRS letters) but not full representation. However, for most people, audit representation isn't necessary since the majority of audits are simple correspondence audits that you can handle yourself with some guidance. The time difference was minimal for me - maybe an extra 15-20 minutes with FreeTaxUSA since I had to look up a couple of things myself instead of having them explained automatically. But saving $173 works out to paying myself over $300/hour for that extra time, so it's definitely worth it in my situation!

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This is exactly the kind of real-world comparison I was looking for! I've been paying TurboTax's increasingly high fees for years without really questioning whether I was getting value for the extra cost. Your side-by-side test proves what I suspected - that most of us are overpaying for the same tax calculations. I'm curious about one thing though - did you notice any significant differences in the error-checking features? TurboTax is pretty aggressive about flagging potential issues or missed deductions. Does FreeTaxUSA have similar safeguards to catch mistakes before filing? Also, for anyone considering the switch, it might be worth doing what the original poster did - run your taxes through both systems one final time to build confidence before making the full switch. The peace of mind of seeing identical results is probably worth the extra hour of time investment.

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Javier Cruz

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Remember that the IRS looks at the "ordinary and necessary" standard for business deductions. Ask yourself: Is paying for a college degree an ordinary and necessary expense in your specific industry? For most businesses, general college tuition doesn't meet this test. The safest approach is to take business deductions only for targeted education that directly impacts your current business and take personal education credits for your degree program. Don't risk aggressive deductions that could trigger an audit!

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Emma Wilson

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This "ordinary and necessary" standard trips up so many small business owners. I've seen people try to write off everything from general college degrees to language classes that weren't relevant to their actual business.

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Great discussion everyone! As someone who's been through this exact situation, I want to emphasize the importance of documentation if you do decide to deduct any education expenses. The IRS will want to see a clear business purpose for each course or program. I keep a detailed log showing how each class directly relates to my current business operations - not just vague connections, but specific skills I'm using in my work. For example, if I take a project management course, I document which client projects I'm applying those skills to and how it's improving my business performance. Also worth noting - even if some courses qualify as business deductions, you still need to be careful about how you categorize them. The IRS distinguishes between education that maintains/improves current skills versus education that qualifies you for a new trade. Make sure you're crystal clear about which category your expenses fall into before claiming any deductions.

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NeonNebula

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This documentation approach is exactly what I needed to hear! I've been keeping pretty loose records, but your specific example about the project management course really shows how detailed I need to be. Do you have any recommendations for how to structure this documentation? Like should I keep a spreadsheet tracking each course, the business justification, and specific examples of how I'm applying the skills? I want to make sure I'm prepared if the IRS ever questions these deductions.

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Pregnant and being told to claim unemployment instead of maternity leave - legal?

So I'm in a bit of a sticky situation with my small business employer (we're a team of 7 people total). I'm currently pregnant and due in December, and my boss just had a conversation with me about my upcoming maternity leave that has me concerned. They're suggesting that instead of providing paid leave, I should file for unemployment and claim that I was laid off due to business slowdown. They said they'd hold my position for me and give me a return-to-work date in February. They mentioned our sales numbers are genuinely down from last year, so there's a "legitimate" reason they could use if unemployment office checks. When I had my first baby in 2023, they initially suggested the same thing. I tried filing but was honest about having a baby and got denied (obviously). They ended up paying me $400 weekly for the 8 weeks I was out instead. This time they're explicitly telling me NOT to mention my pregnancy and just say I was laid off. They're assuring me I "should get paid no problem" and won't have to report job searching activities. I'm really uncomfortable with this. Two mom friends I asked said this sounds like fraud, and when I privately asked my assistant manager, they agreed it seems sketchy. I'm worried about tax implications too - I'll be claiming a newborn on my taxes for the exact period I was supposedly "laid off." My employer has been good to me in many ways, and I don't want to get them in trouble, but I also don't want to commit fraud. I need income during my maternity leave, but this doesn't feel right. Is what they're suggesting legal? Could I get in trouble? Are there other options I should explore?

Yuki Sato

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This is definitely unemployment fraud and you should absolutely not do this. I work in tax preparation and see the aftermath of these situations regularly. The IRS and state unemployment offices have sophisticated cross-referencing systems that will catch discrepancies between your unemployment claims and tax filings. When you file your 2025 taxes claiming a newborn dependent born in December, but also received unemployment benefits during that same period for being "laid off," that's going to trigger automatic flags in the system. The timeline will be obvious - you can't be actively seeking work while in the hospital giving birth and caring for a newborn. Beyond the fraud issue, there are legitimate options you should explore first. Many people don't realize that short-term disability insurance often covers pregnancy and childbirth recovery. Check your employee benefits package - you might already have this coverage. Also, some states have temporary disability insurance programs that provide partial wage replacement during recovery from childbirth. If your employer is genuinely experiencing financial hardship and can't provide paid leave, they should be honest about that rather than suggesting illegal workarounds. There may be legitimate ways to structure unpaid leave with partial income replacement through proper channels. Document everything about these conversations and consult with an employment attorney if needed. Your employer putting you in this position is problematic on multiple levels.

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Tami Morgan

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As someone new to this community, I really appreciate seeing all these detailed responses about such an important issue. This thread has been incredibly educational - I had no idea how sophisticated the cross-referencing systems are between unemployment and tax filings. @de30959ad4b5 Your point about the automatic flags when filing taxes with a newborn dependent during the same period as unemployment claims is particularly eye-opening. It seems like the technology makes it almost impossible to get away with this kind of fraud, even if someone wanted to try. The consensus here seems clear that what the employer is suggesting is absolutely not worth the risk. I'm curious though - for someone in Carmen's situation, what would be the best first step? Should she start by checking her current benefits package for short-term disability, or would it be better to contact an employment attorney first to document these problematic conversations with her employer? Thanks to everyone for sharing their knowledge and experiences. This kind of information could save someone from making a very costly mistake.

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As someone who's dealt with similar employer pressure in the past, I want to emphasize how important it is to trust your instincts here. You already know this feels wrong, and you're absolutely right to be concerned. What your employer is suggesting isn't just risky - it's a federal crime. Unemployment fraud can result in criminal charges, hefty fines, and having to repay benefits with penalties and interest. The fact that they're explicitly telling you to lie about your pregnancy makes this even more serious. I'd recommend taking these steps immediately: 1. Document everything - follow up any verbal conversations with emails "confirming what we discussed" 2. Review your employee handbook and benefits package for any short-term disability coverage 3. Research your state's pregnancy/disability benefits programs 4. Consider consulting with an employment attorney, especially since your employer is pressuring you to commit fraud Remember, a good employer should be helping you find legitimate solutions, not asking you to break the law. The fact that they've suggested this before shows a pattern of problematic behavior that could put other employees at risk too. Your financial needs during maternity leave are valid and important, but there are legal ways to address them. Don't let your employer's "solution" jeopardize your future financial security and legal standing.

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