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Kylo Ren

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I've been using FreeTaxUSA Business for my S-Corp for the past two years and wanted to throw another option into the mix that nobody has mentioned yet. It's significantly cheaper than all the options discussed here (around $25 for federal business filing) while still being user-friendly for first-time S-Corp filers. The interface isn't as polished as TurboTax, but it's more intuitive than TaxAct and includes helpful explanations for S-Corp specific issues. What I really appreciate is that it doesn't try to upsell you on additional services every few screens like some of the bigger names do. That said, after reading about the document analysis services mentioned by others in this thread, I'm definitely going to try that approach this year before starting my actual filing. Finding an extra $3,000-5,000 in legitimate deductions would easily pay for itself many times over. One thing I learned from experience: whichever software you choose, don't rush through the depreciation sections. I made mistakes there in my first year that cost me money, and it's one area where the cheaper software options sometimes don't provide as much guidance. Take your time or get that professional review that Andre mentioned - it's worth it for peace of mind on your first S-Corp return. With your revenue level, any of these software options should handle your needs well, but the key is making sure you're maximizing your deductions and handling the S-Corp specific requirements correctly.

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Yuki Sato

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FreeTaxUSA Business is a great budget option I hadn't considered! At $25 for federal filing, that's incredibly affordable compared to the $150+ range for TurboTax Business. Your point about not being constantly upsold is appealing too - I hate when software tries to nickel and dime you at every step. I'm curious about your experience with their S-Corp guidance though. You mentioned it includes helpful explanations for S-Corp specific issues - does it walk you through things like reasonable compensation requirements and shareholder distribution reporting as thoroughly as the more expensive options? Or is it more basic explanations? Also, since you mentioned making depreciation mistakes in your first year, what kind of errors should newcomers watch out for? Was it about choosing between Section 179 expensing vs. traditional depreciation, or something else entirely? The combination of FreeTaxUSA + document analysis services could be an incredibly cost-effective approach if the software is solid enough for first-time filers. Thanks for bringing up this option!

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Sophia Miller

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As a tax professional who's helped dozens of small business owners transition to S-Corp filing, I want to add some perspective on the software choices and emphasize a few critical points that haven't been fully addressed. First, regarding software selection: while TurboTax Business is indeed the most user-friendly, the real value isn't just in the interface - it's in their error-checking algorithms. S-Corps have specific compliance requirements that can trigger audits if handled incorrectly, and TurboTax tends to catch more of these potential issues before filing. However, I'm seeing a concerning trend in this discussion where people are focusing heavily on maximizing deductions without enough emphasis on documentation and compliance. The IRS has been increasing S-Corp audits, particularly around officer compensation and personal vs. business expense classification. For your specific situation with $87k revenue, here's what I'd strongly recommend: 1. Pay yourself a reasonable W-2 salary FIRST (probably $35-45k in your range depending on your role/industry) 2. Document everything meticulously - the software won't save you if you don't have proper backup for your deductions 3. Be extremely careful with home office, vehicle, and meal deductions - these are audit magnets The document analysis services mentioned here can be valuable, but remember: finding deductions is only half the battle. You need to be able to defend them with proper documentation if questioned. Make sure any service you use also provides guidance on documentation requirements, not just identification of potential deductions. Whatever software you choose, budget for professional review of your completed return before filing. The cost of a CPA review ($200-500) is minimal compared to potential penalties and interest from compliance mistakes.

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Emma Johnson

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This is exactly the kind of professional perspective I was hoping to see in this thread! Your point about focusing on compliance over just maximizing deductions really hits home - I've been so caught up in finding every possible deduction that I hadn't fully considered the audit risk implications. Your salary recommendation of $35-45k for someone with $87k in revenue is really helpful context. Most of the online resources I've found are vague about what "reasonable compensation" actually means in practice. Is that range based on industry standards, or is there a general formula you use as a starting point? The documentation emphasis is sobering but important. When you mention that deductions need to be "defendable," what does proper backup documentation look like for common S-Corp expenses like home office or business meals? Are we talking about just keeping receipts, or is there more detailed record-keeping required? I'm definitely planning to budget for professional review now - the $200-500 range you mentioned seems very reasonable for the peace of mind, especially compared to potential audit costs and penalties. Would you recommend having the review done before filing, or is it worth having someone look over my approach and documentation before I even start with the software?

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Just wanted to add another data point for anyone reading this thread - I've been filing from Singapore for 5 years now and can confirm that foreign wages definitely go on Line 1a. One thing I learned the hard way is to make sure you're using the correct exchange rates when converting SGD to USD. The IRS requires you to use the Treasury Department's yearly average exchange rates (available on their website) rather than spot rates or your bank's conversion rates. This can make a meaningful difference in your reported income amount. Also, since you mentioned you're using tax software, double-check that it's properly handling the Singapore tax year vs US tax year difference. Singapore's tax year runs from January to December, but make sure you're reporting the right period's income on your US return. I made this mistake my first year and had to file an amended return. The Foreign Earned Income Exclusion should cover your full $58k income assuming you meet the physical presence test (330 days in Singapore during any 12-month period). Keep a simple spreadsheet tracking your days in/out of Singapore - it'll save you headaches later if the IRS ever asks for documentation.

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LunarLegend

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This is incredibly helpful, especially the point about using Treasury Department exchange rates! I had no idea there was a specific requirement for which rates to use. I've been using whatever rate my bank showed me when I converted money, which could definitely be causing issues. Quick question about the spreadsheet tracking - do you just track the actual dates you're in/out of Singapore, or do you also note the reasons for travel? I'm planning a few trips back to the US this year to visit family and want to make sure I'm documenting everything properly for the physical presence test. Also, when you mention the Singapore vs US tax year difference, are you referring to making sure the income reported aligns with the US calendar year (Jan-Dec) even though that might span across different Singapore tax periods? Want to make sure I understand this correctly before I file.

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@LunarLegend For the spreadsheet tracking, I just keep it simple - date in, date out, and destination/origin. You don't need to document reasons for travel for IRS purposes, but I do include a brief note (like "family visit" or "business trip") just for my own records. The IRS only cares about the actual days you were physically present in a foreign country. Regarding the tax year alignment - yes, exactly! You need to report income that corresponds to the US tax year (January 1 to December 31) on your US return, regardless of when Singapore's tax year runs or when you received certain payments. So for your 2024 US tax return, you'd report all income earned from January 1, 2024 to December 31, 2024, even if some of that spans different Singapore tax periods. One more tip: the Treasury exchange rates are published annually, usually around March/April for the previous year. Until then, you can use the Federal Reserve's daily rates, but switch to the Treasury annual average once it's available. Makes everything much cleaner and more defensible if questioned.

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Just want to echo what everyone else has said - your Singapore wages definitely belong on Line 1a of Form 1040, not Line 1h. I went through this exact same confusion when I first moved to Hong Kong for work. One thing that might help clarify the logic: Line 1a is for ALL wages and salaries, regardless of the source country. Line 1h is specifically for miscellaneous income that doesn't fit into any of the other defined categories on the form (like gambling winnings, jury duty pay, etc.). Your regular employment income from Singapore is still wages, just foreign wages. The fact that you'll be excluding it later with Form 2555 doesn't change where you initially report it. Think of it as a two-step process: first you report ALL your worldwide income in the appropriate sections, then you apply exclusions and credits to reduce your taxable amount. Since you're earning about $58k USD equivalent and have been in Singapore for 3 years, you should easily qualify for the full Foreign Earned Income Exclusion (assuming you meet the physical presence test). Just make sure your tax software is set up to handle foreign income properly - most major programs have specific workflows for expats that will walk you through both the initial reporting and the exclusion forms.

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This is such a helpful thread! As someone who just moved to Singapore last month for work, I'm already dreading next year's tax season. It's reassuring to see that so many people have successfully navigated this process. One question I have - since I'll only be in Singapore for part of 2025 (started in December 2024), do I need to prorate anything for the Foreign Earned Income Exclusion, or does it work differently when you're not abroad for the full tax year? I'm assuming I'll still report all my income on Line 1a regardless, but wondering about the exclusion calculation for a partial year abroad. Also, @QuantumQuester, when you mention making sure tax software is set up properly for foreign income - are there specific settings or flags I should look for? I want to make sure I don't accidentally mess something up in the setup process.

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Has anyone used TurboTax to handle this kind of situation? Do they have a good section for sorting out 1099 deductions vs employee expenses? Trying to figure out if I need to pay for a CPA this year.

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TurboTax Self-Employed asks pretty good questions about your contractor status and walks you through potential deductions. It'll ask about your work situation which might help identify if you're misclassified. But it won't file those SS-8 forms for you if you decide to challenge your classification.

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Taylor To

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I'm dealing with a very similar situation and wanted to share what I learned from my research. The key issue here isn't just the mileage deduction - it's the misclassification problem that several others have mentioned. For the mileage question specifically: No, you cannot deduct your daily commute to the carpentry shop, even as a 1099 contractor. The IRS considers travel from your home to your regular place of business as personal commuting expenses, regardless of your tax classification. However, here's what you CAN potentially deduct as a legitimate contractor: - Travel between different job sites (not from home to the first site) - Tools and equipment you purchase yourself - Work-related supplies - Portion of vehicle expenses for business use (not commuting) - Professional development/training costs But here's the bigger concern - based on your description, you're likely misclassified. If your boss controls your schedule, provides tools, and treats you like an employee, you should probably be getting a W-2. This misclassification is costing you money in additional self-employment taxes. I'd recommend tracking your actual work arrangement details (who provides tools, who sets your schedule, do you work for other companies, etc.) and consider getting professional guidance on whether to challenge your classification with the IRS.

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Aisha Rahman

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This is really helpful, thank you for breaking it down so clearly! I'm new to all this tax stuff and honestly feeling pretty overwhelmed. Just to make sure I understand correctly - even though my boss keeps telling us we can deduct the mileage, that's definitely wrong? And the fact that he provides most of our tools and tells us exactly when to show up probably means we should be employees, not contractors? I'm worried about rocking the boat at work, but it sounds like this misclassification could be costing me a lot of money. How risky is it to file those forms with the IRS? Could my boss retaliate somehow?

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PrinceJoe

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I just went through this exact same worry last month! My W2 from my seasonal job had box D completely empty and I spent way too much time researching whether it would cause problems. Turns out it's totally fine - I filed successfully and got my refund without any issues. What really helped me was understanding that the control number is basically just like a tracking number that some employers use for their own organization. It's kind of like how some stores print reference numbers on receipts and others don't - both receipts are equally valid, just different internal systems. The key thing is making sure all your actual income and withholding amounts are correct in the other boxes. Those are what the IRS actually cares about when processing your return. Your tax software not flagging it is a good sign - these programs are pretty good at catching real problems versus optional fields. Don't let this delay your filing! Sounds like you're being thorough by checking everything, which is great, but this particular issue definitely shouldn't hold you back.

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Caden Turner

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Thanks for sharing your experience! It's so reassuring to hear from someone who actually went through the same worry and filed successfully. I love your analogy about receipt reference numbers - that really makes it click for me. I've been overthinking this way too much when I should just focus on the important stuff like you said. Really appreciate everyone in this thread taking the time to help us anxious first-time filers feel more confident!

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I'm new to filing taxes and was getting really nervous about a similar issue - my W2 has the control number but it looks like it might be wrong (it's just "001" which seems too simple). After reading all these responses though, I feel so much better knowing that even if it's completely missing it doesn't matter at all! This thread has been incredibly helpful for understanding what's actually important on a W2 versus what's just optional employer tracking. I've been stressing over every single box thinking they were all critical. Now I know to focus on the wages and withholding amounts instead of worrying about internal reference numbers. Thanks to everyone who shared their experiences and expertise - especially the tax preparer and payroll person who gave professional insights. It's amazing how supportive this community is for people navigating tax season for the first time!

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Nia Thompson

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Don't worry about the "001" - that's actually pretty normal! Many employers use simple sequential numbering for their control numbers, especially smaller companies. I've seen control numbers that are just "1", "2", "3" etc. There's no specific format requirement since it's purely for the employer's internal use. Your instinct to focus on wages and withholding is exactly right. Those are the numbers that actually get reported to the IRS and need to match your return. The control number could be "001", "ABCDEF", or completely missing - none of those scenarios would affect your ability to file successfully. It sounds like you're being really thorough in checking everything, which is great! That attention to detail will serve you well, just remember to focus it on the boxes that actually impact your taxes.

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Ravi Choudhury

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This thread has been incredibly helpful! I had no idea there were so many considerations beyond just the tax savings. As someone who's been through a similar situation, I wanted to share what we ultimately decided to do. After reading about all the potential complications (student loans, health insurance, etc.), my fiancΓ© and I decided to stick with filing separately this year and just accept the higher tax bill. We realized that the $3,200 in potential savings wasn't worth the risks of committing tax fraud or the complications it could create with our other financial obligations. Instead, we're planning to get legally married in a small courthouse ceremony this December (before our big wedding next summer) so we can file jointly for next year's taxes. This way we get the legitimate tax benefits going forward without any of the legal risks. For anyone else in this situation - definitely run the numbers on how marriage would affect your student loan payments, health insurance premiums, and any other income-based benefits before making the decision. The tax savings might be offset by increases in other areas. Thanks everyone for keeping me from making a costly mistake!

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Ravi Kapoor

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That sounds like a really smart approach! You're absolutely right that the tax savings aren't worth the legal risks. I'm in a very similar situation - my partner and I were also tempted by the potential savings our tax preparer mentioned, but after reading through all these responses, we're definitely going to file separately this year. The courthouse ceremony idea is brilliant! We hadn't really considered doing a small legal ceremony separate from our big wedding, but it makes total sense from a financial planning perspective. Plus it gives you a whole year to see how the marriage affects all your other financial obligations before the big celebration. Thanks for sharing your decision - it really helps to hear from someone who went through the same thought process!

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Just wanted to add my perspective as someone who works in tax preparation - this thread is spot on about the legal requirements. I see this confusion come up fairly regularly, especially with younger couples who are living together and sharing expenses. One thing I always tell clients is that the IRS definition of "married" is very specific and binary - you either are legally married under state law or you're not. There's no "engaged" filing status, no "domestic partner" option for federal taxes, and no exceptions for couples who live together or share financial responsibilities. The $3,200 potential savings your tax preparer mentioned is probably real - married filing jointly often does result in significant tax benefits, especially when one partner earns substantially more than the other. But as others have mentioned, claiming that status when you're not legally married would constitute filing a false return. If you're serious about the tax savings, getting married before December 31st really is your only legitimate option. Just make sure to consider all the other financial implications (student loans, health insurance, etc.) that others have mentioned before making that decision. I'd also echo the recommendation to find a new tax preparer - anyone suggesting unmarried couples can file jointly either doesn't understand basic tax law or is encouraging fraud. Neither is someone you want handling your taxes.

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Ethan Clark

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Thank you for this professional perspective! It's really reassuring to hear from someone who actually works in tax preparation confirming what everyone else has been saying. I have to admit, when our tax preparer first mentioned the joint filing option, I got excited about the savings and didn't immediately think to question whether it was actually legal. Your point about the IRS definition being "binary" really drives it home - there's no gray area here like I was hoping there might be. I think part of the confusion came from the fact that we've been living together for three years, sharing a mortgage, and basically operating as a married couple financially. But obviously that doesn't matter for tax purposes. We're definitely going to find a new tax preparer for next year. Do you have any recommendations for what questions we should ask to make sure we're working with someone competent? I want to avoid this situation again and find someone who actually knows the tax code properly. Also, since we're now planning to do a courthouse ceremony in December, do you know if there are any specific timing considerations we should be aware of? Like does the marriage need to be recorded by a certain date, or is it just based on when the ceremony actually happens?

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