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Ask the community...

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Mary Bates

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Building on what others have shared, I've found that creating a standardized intake process really helps streamline due diligence while keeping clients happy. I use a checklist approach where I explain upfront what documents we'll need and why - most clients appreciate the transparency. One tip that's saved me time: for returning clients, I review their previous year's file before they arrive and prepare a personalized document list. This way I'm only asking for what's actually needed based on their specific situation, not a generic "bring everything" list. Also, don't forget about the record retention requirements - you need to keep due diligence documentation for at least three years after the due date of the return. I learned this the hard way when the IRS requested documentation for a 2019 return and I had already purged some files. For new preparers especially, I'd recommend erring on the side of collecting more documentation initially until you get comfortable recognizing which situations require what level of proof. It's much easier to streamline your process over time than to deal with penalties for insufficient due diligence.

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Mila Walker

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This is really helpful advice, especially about preparing personalized document lists for returning clients. I'm just starting out in tax prep and was definitely falling into the "bring everything" trap that was annoying clients. Quick question about record retention - when you say three years after the due date, does that mean three years from April 15th of the filing year, or three years from when the return was actually filed if it was filed late? I want to make sure I'm not purging files too early. Also, do you have any recommendations for organizing the due diligence documentation? I'm struggling with whether to keep everything in physical files or scan everything digital.

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Great question about the record retention timeline! It's three years from the due date of the return (April 15th for most returns), not from when it was actually filed. So for a 2023 return, you'd need to keep records until April 15, 2027, even if the return was filed late. For organization, I'd strongly recommend going digital if possible. I scan everything and organize by client folders with subfolders for each tax year. Physical storage gets overwhelming fast, especially if your practice grows. Just make sure you have good backup systems - I learned that lesson when a computer crash almost lost two years of client files. One more tip for new preparers: create a simple tracking sheet that shows which documents you've collected for each client and which credits they're claiming. During busy season it's easy to lose track of what you have versus what you still need from clients.

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As someone who's been through several IRS reviews, I can't stress enough how important it is to document everything properly. One thing I've learned is that the IRS isn't just looking for the documents themselves, but evidence that you actually reviewed them and asked appropriate follow-up questions. For EITC specifically, make sure you're documenting not just that you collected a birth certificate, but that you verified the child's age makes them a qualifying child, that their SSN is valid for work purposes, and that they haven't been claimed by someone else. I keep a simple checklist for each credit that goes beyond just "document collected" to include "eligibility verified." Also, don't overlook the interview requirements. You're required to ask specific questions about each credit and document the taxpayer's responses. I use a standard interview form that covers all the key questions for EITC, CTC, and HOH, and I have clients initial each section after we discuss it. The good news is that once you get a system in place, it becomes routine. Most clients actually appreciate that you're being thorough - it shows you're protecting them too.

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Jamal Wilson

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This is exactly the kind of systematic approach I wish I'd started with! The interview documentation piece is something I've been struggling with - I ask the questions but wasn't documenting the responses well enough. Do you have a template for that interview form you mentioned? I'm trying to figure out how detailed the documentation needs to be. Like if someone says their child lived with them all year, do I need to write down their exact words or is a checkmark sufficient? Also, when you say "eligibility verified" for things like SSN validity, are you actually checking that somehow or just confirming with the client that it's correct?

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Just a warning - make absolutely sure you and your parents are on the same page about your dependent status! My brother claimed education credits for himself not realizing our parents were going to claim him as a dependent. It triggered IRS notices for everyone and was a huge mess to fix.

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That happened to me too! It delayed both my refund and my parents' refund by months while the IRS sorted it out. They had to submit additional documentation and I had to file an amended return. Total nightmare.

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Exactly! And the worst part was that nobody got the education credit in the end because of the way the paperwork had to be corrected. The IRS made us file specific forms to resolve the conflict, and by the time everything was sorted out, we'd missed some deadline for claiming the full credit amount. Make sure your parents know not to file their taxes without including your 1098-T information!

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This is such a common situation for college students! I went through the exact same thing two years ago. Here's what I learned: You can definitely file your own return for your $14,000 income without waiting for your parents - just make sure to check the box that says you can be claimed as a dependent on someone else's return. You'll get any refund from overwithholding on your wages. However, the education credits from your 1098-T will need to go on your parents' return since they claim you as a dependent. The American Opportunity Credit can be worth up to $2,500, so it's definitely worth having a conversation with them about filing sooner rather than later. One thing that helped in my family was offering to organize all the tax documents for my parents and maybe even help them find a tax preparer if that's what's causing the delay. Sometimes parents put off filing because they're overwhelmed by the paperwork, not because they want to wait until April. Also, consider talking to your financial aid office about emergency funds or payment plan options for summer classes while you're waiting for this to get sorted out. Many schools have resources for situations exactly like this.

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This is really helpful advice! I never thought about offering to help organize their tax documents - that might actually be what's holding them up. My parents always seem stressed about tax season and maybe they're just procrastinating because it feels overwhelming. The emergency funds idea is smart too. I was so focused on getting my refund that I didn't even think to ask my school about other options. Do you know if most schools have these kinds of emergency funds available? And would using them affect my financial aid for next year? Also, when you say "check the box that says you can be claimed as a dependent" - is that on the main 1040 form or somewhere else? I want to make sure I don't mess this up since everyone's saying how important it is to coordinate properly with parents.

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Donna Cline

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Just make sure you're reporting everything correctly! My brother tried to just "net" his gambling wins and losses a few years back (only reporting the difference) and got hit with an audit. The IRS requires you to report the FULL amount of the 1099-MISC as income, then deduct losses separately on Schedule A if you itemize. Don't make that mistake - the IRS computers will flag the mismatch between your reported income and what Underdog submitted on your 1099.

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This is so important. The IRS matching system will immediately flag a return if the 1099 amounts don't match what you report. I'd add that you should also keep records for at least 3 years in case you get audited.

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Luca Marino

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I went through almost exactly this situation two years ago - had a big 1099-MISC from FanDuel but overall losses for the year from other sites. Here's what I learned the hard way: You absolutely MUST report that full $10,400 as income even though you had net losses. Don't try to just report the "net" - the IRS computers will catch that immediately since Underdog already reported paying you $10,400. The good news is you can deduct your gambling losses, but only if you itemize deductions on Schedule A. You can deduct up to the amount of your winnings ($10,400 in your case), so theoretically you could zero out the tax liability from the gambling income. However, here's the catch that got me - you need to compare your total itemized deductions (including the gambling losses) to the standard deduction. If your standard deduction is higher, you're better off taking that and just paying tax on the $10,400. For the Bovada losses, keep every record you can find - transaction history, bank statements showing transfers, screenshots of your account summary. The IRS doesn't specifically exclude offshore sites, but documentation is absolutely critical. One more thing - don't forget about state taxes! Some states don't allow gambling loss deductions at all, so you might owe state tax on the full amount even if you can offset it federally.

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Zara Khan

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This is really helpful, thanks for sharing your experience! I'm wondering about the documentation part - when you say "every record you can find" for the Bovada losses, how detailed did you need to get? Like did you need to document every single bet, or was it enough to show deposits/withdrawals and maybe monthly summaries? I'm trying to figure out how much work I'm looking at here to get my records together.

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Another thing to consider - if you're using accounting software like QuickBooks, they usually have 1099 preparation built in. You can e-file directly through their system if you've been tracking your contractor payments correctly throughout the year. I've used this for the past 3 years and it's super simple - the system generates all the forms automatically based on how you've categorized payments. Worth checking if you're already using any accounting software!

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Is this true for the cheaper versions of QuickBooks too? I have QB Self-Employed and wasn't sure if that includes 1099 filing or if it's only in the more expensive tiers.

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Zainab Ahmed

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QB Self-Employed does include 1099 preparation and e-filing! I use it myself and it's one of the features that makes it worth the subscription cost. You can generate and file 1099-NECs directly through the platform as long as you've been properly categorizing your contractor payments throughout the year. The system walks you through the whole process and handles both the IRS filing and sending copies to your contractors. Just make sure you have all their W-9 information entered correctly in your contractor profiles before you start the filing process.

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I went through this exact same stress last year! The IRS really doesn't make this process user-friendly at all. Here's what worked for me: Since you mentioned you already ordered the paper forms, you can actually request a filing extension if they don't arrive in time. Form 8809 gives you an automatic 30-day extension for filing 1099s with the IRS (though you still need to get copies to your contractors by Jan 31). For the digital route, I ended up using the IRS FIRE system which is completely free but has a bit of a learning curve. If you want something more straightforward, I'd recommend checking if your bank offers any business tax services - many of them have partnerships with 1099 filing companies and can get you discounted rates. One important tip: make absolutely sure you have the correct TIN/EIN for each contractor before filing anything. I had to file corrected forms last year because one contractor gave me their SSN instead of their business EIN, and that was a whole other headache. Don't panic though - you have more time than you think, especially if you file electronically. The key is just picking one method and moving forward rather than getting paralyzed by all the options!

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Been using Cash App for refunds for 3 years now and honestly it's been hit or miss. Got my refund in 2 days one year, then last year it took almost a month with zero explanation from support. The $25k limit thing is real too - if you're expecting a big refund you might hit that cap. I'd say if your refund is under $5k and you don't mind potentially waiting longer, it's okay. But for peace of mind, traditional bank is definitely the safer route.

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appreciate the honest breakdown! the inconsistency is what worries me most. like why would it take 2 days one year and a month the next? seems like too much of a gamble when we're talking about tax money

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Ruby Garcia

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I used to work at a bank and saw this stuff all the time. Cash App and other fintech apps are great for everyday transactions but they're not built for handling large government deposits like tax refunds. The IRS sends refunds through the ACH network, and traditional banks have way better infrastructure to handle these transfers smoothly. Plus if something goes wrong, good luck getting actual human support from Cash App - banks at least have branch locations and phone reps who can actually help you track down your money. Just open a basic checking account at a credit union if you don't want big bank fees.

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this is super helpful info! @Ruby Garcia thanks for the insider perspective. had no idea about the ACH network differences. definitely gonna look into credit unions now - any specific ones you d'recommend for someone who just needs basic checking for tax stuff?

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