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As someone who made the transition from W2 to 1099 about 18 months ago, I can definitely relate to that overwhelming feeling! Here's what I wish someone had told me from the start: First, don't panic about the quarterly payments - they're basically just spreading your tax burden throughout the year instead of getting hit with a massive bill in April. I use a simple rule: every time I get paid, I immediately move 30% into a separate "tax account" that I don't touch except for quarterly payments. The biggest mistake I made early on was not tracking expenses properly. Even small things add up - software subscriptions, office supplies, professional development courses, even a portion of your internet bill if you work from home. I use a simple spreadsheet to track everything, but there are also apps that make it easier. Since you're planning to start a business next year, I'd recommend getting comfortable with basic bookkeeping now. It'll make that transition much smoother. Also, consider whether you want to form an LLC or stay as a sole proprietor - each has different tax implications. The learning curve feels steep at first, but once you get into a routine, it becomes second nature. You've got this!

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Mila Walker

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This is exactly the kind of practical advice I was hoping for! The 30% rule seems to come up a lot in these responses, so I'm definitely going to start doing that immediately. Quick question about the expense tracking - when you say "portion of your internet bill," how do you actually calculate that? Do you just estimate what percentage you use for work vs personal, or is there a more official way the IRS expects you to do it? Also really appreciate the heads up about LLC vs sole proprietor. I hadn't even thought about the tax differences yet, but I should probably start researching that now since I'm planning to formalize things next year anyway.

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For the internet bill portion, the IRS expects you to be reasonable and consistent. I calculate it based on how much time I actually use internet for work versus personal use. Since I work from home about 8 hours a day and use internet for personal stuff maybe 2-3 hours, I deduct roughly 70% of my monthly internet bill. The key is being able to justify your percentage if questioned. Some people get more precise and track actual work hours vs total internet usage time, but as long as you're not claiming 100% when you clearly use it for personal stuff too, you should be fine. Just keep good records of your reasoning. For LLC vs sole proprietor, the main tax difference is that an LLC can elect S-Corp status, which might save you money on self-employment taxes once you're making good income. But there are also additional paperwork requirements and costs. Definitely worth researching now since the decision affects how you'll need to structure things from day one.

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Jayden Reed

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Dylan, welcome to the 1099 world! I made this exact transition about 2 years ago and totally understand that overwhelming feeling. Here's my practical advice from someone who learned some lessons the hard way: **Immediate action items:** 1. Set up a separate business checking account TODAY - this alone will save you hours during tax time 2. Start the 30% rule everyone mentioned - I actually do 32% to be safe 3. Download a mileage tracking app if you drive anywhere for work **Quarterly payments reality check:** Yes, you technically should make them if you'll owe $1000+, but here's what I learned - the penalty for not making them isn't catastrophic if this is your first year. That said, don't make it a habit! I paid about $200 in penalties my first year, which taught me to get serious about quarterly payments going forward. **Business planning tip:** Since you're thinking about formalizing a business next year, start treating everything like a business now. Save all receipts, track everything, and get comfortable with basic accounting concepts. When you do incorporate, you'll already have good habits and historical data. The tax software and services people mentioned are helpful, but honestly, Form 1040-ES and the IRS website have everything you need to calculate your quarterly payments. Start simple, then add complexity as needed. You've got this! The first year is always the scariest, but it becomes routine quickly.

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Oliver Cheng

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This is such solid, practical advice! I really appreciate the "reality check" perspective on the penalties - it helps to know that while I should definitely aim to make quarterly payments, a first-year mistake isn't going to ruin me financially. The separate business checking account tip is something I keep seeing mentioned but haven't done yet. I'm definitely setting that up this week. Quick question though - do you recommend a specific type of business account, or is any basic business checking account fine for a solo contractor? Also love the point about treating everything like a business from day one. I think that mindset shift will probably help with the transition to actually incorporating next year too. Thanks for taking the time to share your experience!

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For business checking accounts, honestly any basic business account works fine when you're starting out as a solo contractor. I went with a local credit union that had no monthly fees for business accounts under a certain balance. The big banks (Chase, Bank of America, etc.) tend to have higher fees, but they also have better online tools and more locations if that matters to you. The main thing is just having it be officially designated as a business account rather than trying to use a personal account for business purposes. Some banks get picky about business transactions going through personal accounts, plus it makes your bookkeeping so much cleaner. Once you incorporate next year, you'll probably want to switch to an account that's specifically set up for your business entity type anyway, so don't stress too much about getting the "perfect" account right now. Just get something basic that separates your business money from personal money - that's the real game-changer for tax organization!

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Not to be that person but like... maybe pay your loans? šŸ‘€

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Benjamin Kim

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read the room bestie 🤮

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in this economy? lmaooo

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Emma Morales

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Been through this exact situation! Yes, if your loans are in default, they WILL take your refund regardless of where you file (Credit Karma, TurboTax, etc.). The offset happens at the federal level after processing. BUT - you're not totally screwed! You can still get out of default through loan rehabilitation (9 on-time payments) or consolidation. Just make sure to start the process ASAP because it takes time. Also worth checking if you qualify for any hardship deferrals or income-driven repayment plans once you're out of default. Don't give up! šŸ’Ŗ

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This is super helpful! Quick question - how long does the rehabilitation process actually take? Like from start to finish before they stop taking refunds? I'm worried about timing with tax season coming up 😰

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Eli Wang

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If this is your first year filing with allocated tips, don't stress too much about not having perfect records for this year. Just be aware of what they are, report them correctly, and then start keeping better records going forward. I got allocated tips for years before I figured out how to handle them properly!

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Malik Thomas

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As someone who's been through this exact situation, I totally get how overwhelming allocated tips can be when you're doing your taxes for the first time! The good news is that once you understand what they are, they're not as scary as they seem. Here's the simple breakdown: Your restaurant is required to allocate tips if the total reported tips from all employees is less than 8% of food/beverage sales. These allocated tips in Box 8 represent what the IRS thinks you earned but didn't report to your employer during the year. For your tax return, you'll need to include these as income AND pay the Social Security/Medicare taxes on them using Form 4137 (TurboTax will help with this). The key thing to remember is that you CAN dispute these allocated tips if you have records showing you actually received less - but without documentation, you'll need to report the full allocated amount. Going forward, definitely start tracking your daily tips! Even a simple notebook or phone app will save you from this headache next year. Good luck with your first self-prepared return - you've got this!

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Oscar O'Neil

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This is a really frustrating situation, and I feel for you having to deal with this mess. As others have mentioned, employers are absolutely required to withhold federal income tax based on your W4 - they can't just decide not to do it. Since you have your original W4 showing you claimed 0 exemptions and your 2024 W-2 shows $0 federal withholding in Box 2, you have solid documentation that this was their error, not yours. The fact that they withheld correctly in 2023 but not 2024 suggests something changed in their payroll system or process. A few things to consider while you're waiting for HR to respond: 1. Request a copy of what W4 they have on file for you currently - sometimes forms get lost or replaced incorrectly 2. Ask for detailed payroll records showing how your withholding was calculated (or not calculated) 3. Document all your communications with HR about this issue Even though you'll still need to pay the taxes you owe, having this documentation could be important if the IRS assesses any penalties. You might also want to look into whether your employer could be liable for any interest or penalties you incur due to their mistake - that would probably require talking to a tax professional though. Definitely keep pushing HR for answers. This kind of payroll error affecting someone's entire tax year is a serious issue they need to address and prevent from happening to other employees.

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This is really solid advice, especially about getting a copy of the W4 they currently have on file. I've seen cases where forms get mixed up between employees or someone accidentally overwrites the withholding settings when making other payroll changes. One thing to add - if HR is slow to respond or seems to be stonewalling, you might want to escalate this to whoever manages the payroll department directly, or even to a manager above HR. A $1,875 tax bill due to their error is no small matter, and they should be treating this with appropriate urgency. Also, definitely keep records of any extra costs you incur because of this (like if you have to pay penalties or interest to the IRS, or if you need to hire a tax professional to help sort this out). Depending on your state's laws, you might have grounds to recover those costs from your employer.

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Thais Soares

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This is such a frustrating situation, and unfortunately you're not alone in dealing with payroll withholding errors like this. The good news is that you have solid documentation with your original W4 showing 0 exemptions and the fact that they withheld correctly in 2023. One thing that might help speed up the process with HR is to specifically ask them to provide you with a "payroll withholding history" or "tax setup report" for your account. Most payroll systems can generate reports showing when withholding settings were changed and by whom. This could reveal exactly when and why the federal withholding stopped. You should also request that they confirm in writing what W4 form they currently have on file for you - sometimes forms get lost, misfiled, or accidentally overwritten during system updates. While you'll unfortunately still owe the taxes regardless of their error, document everything related to this issue. Keep copies of all emails with HR, your original W4, paystubs showing zero federal withholding, and your W-2. If the IRS assesses any underpayment penalties, you may be able to request penalty relief by showing this was due to employer error rather than your own negligence. Also consider filing Form SS-8 with the IRS if you suspect they might have incorrectly reclassified your employment status at some point, though based on your description it sounds like you remained a regular employee throughout. Stay persistent with HR - a payroll error affecting someone's entire tax year is a serious compliance issue they need to address and explain.

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Wait till u see how long it takes AFTER the offset... im going on 3 months since they took their chunk and still nothing

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Caleb Stark

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bruhhh dont tell me that 😭

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call the offset hotline at 800-304-3107, they can tell u exactly whats happening

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Niko Ramsey

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Been through this exact situation! California won't touch your state refund for state tax debt - they have their own separate collection process that doesn't involve offsets. The Treasury Offset Program will only take from your federal refund to pay the CA debt. Since you owe $1,200 and your federal is $3k, you should get $1,800 back from federal and your full state refund separately. Just expect the federal to be delayed by a few weeks while they process the offset.

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