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Ask the community...

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Have you tried the "Two Earners/Multiple Jobs" worksheet that comes with the W-4 form? It's specifically designed for couples where both spouses work. It helps you figure out the additional withholding needed to cover the combined income.

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That worksheet is so confusing! I tried it and still somehow ended up owing $2,000 last year. I think the IRS tax withholding calculator on their website is more accurate.

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You're right that it can be confusing. The online withholding calculator is definitely more user-friendly and takes more factors into account. The advantage of the calculator is that it adjusts based on how much has already been withheld this year, while the worksheet is more of a general guideline.

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You're definitely being smart to check this now! I went through something similar when my wife and I both got promotions mid-year. The key thing to remember is that the safe harbor rule can help you avoid penalties - if you pay at least 100% of last year's tax liability (or 110% if your prior year AGI was over $150k), you won't owe penalties even if you end up owing money. Since you mentioned you're around $115k combined, I'd suggest running the IRS withholding calculator first to get a baseline. Then consider whether you want to be conservative and slightly overwithhold to avoid any surprises, or try to get it exactly right. One thing that caught many people off guard this year - if either of you got sign-on bonuses or other lump sum payments with your job changes, those are often under-withheld because they're treated as supplemental income. That could be contributing to your shortfall. The good news is you caught this in April with plenty of time to adjust! Much better than discovering it in January when filing.

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Aria Khan

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This is really helpful advice about the safe harbor rule! I didn't know about that 100% threshold. Since we're making more this year, does that mean we need to pay 100% of what we actually owed last year, or 100% of what our total tax liability was (including what was already withheld)? Also, you mentioned sign-on bonuses - my husband did get a $5,000 signing bonus in March. Should I be worried that wasn't taxed properly? I remember it seemed like a lot was taken out, but maybe not enough for our overall situation.

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TurboTax Desktop Software: How to upload 1099-B documents for tax filing?

I've been struggling with my tax return using TurboTax desktop software this year. I have numerous stock transactions on my 1099-B, and when I tried importing them, there were way too many errors that would take forever to fix manually. So I decided to just enter the summary numbers instead. The problem is, after I entered the summary numbers for my 1099-B, the software never prompted me to upload any supporting documents. I already e-filed my return before realizing this might be an issue. Now I'm worried - is it really required to mail physical copies of my 1099-B to the IRS? I thought brokers already send copies to the IRS directly. I really hate having to mail physical documents - such a waste of time and money. In previous years, I used the TurboTax website (not the desktop software) and remember being able to enter summary numbers AND upload supporting documents. This is my first year using the desktop version, and I'm confused by the difference. Can I still somehow upload my 1099-B electronically? Is there a way to send these to the IRS through their website or even fax them? If I absolutely must mail them, what address do I use? Also, for future reference - does TurboTax desktop software actually allow you to upload 1099-B forms when entering summary numbers, or does it always force you to physically mail Form 8453 with supporting documents? If that's the case, I'm definitely switching back to the online version next year.

Nina Chan

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As someone who's been through this exact headache, I want to add a few practical tips that might help both your current situation and future filing: **For your immediate concern:** Look in your TurboTax files or printed return for Form 8453. If it wasn't generated, you likely don't need to mail anything. If it was created, the form should include the specific IRS mailing address (varies by state) and list exactly which documents to include. **The "3-day rule" isn't as strict as it sounds** - while officially you're supposed to mail within 3 days of e-file acceptance, the IRS processing timeline is much more flexible in practice. Many tax professionals report that documents arriving weeks later are still processed without issues. **For next year:** Consider this hierarchy of approaches with TurboTax Desktop: 1. Import all transactions (fix errors individually if needed) = no mailing required 2. Use TurboTax Online instead = electronic document upload available 3. Enter summary numbers = requires mailing Form 8453 The frustrating part is that TurboTax doesn't make this workflow clear upfront. The software should warn users about the mailing requirement when choosing to enter summary data instead of importing transactions. One silver lining: Since your broker already sent your 1099-B data to the IRS electronically, there's built-in redundancy in the system. The mailing requirement is more about IRS verification procedures than missing information.

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Yara Assad

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This breakdown is extremely helpful, especially the hierarchy of approaches! I'm definitely a newcomer here but dealing with this exact TurboTax Desktop situation. Your point about the "3-day rule" being more flexible in practice is reassuring - I was really stressing about missing some hard deadline. I checked my files and did find Form 8453 was generated, so I guess I technically should mail my 1099-B documents. But knowing that the IRS already has this information from my broker and that there's built-in redundancy makes me feel less anxious about the whole process. The hierarchy you outlined will definitely guide my approach next year. I had no idea that importing transactions (even with errors to fix) would avoid the mailing requirement entirely. TurboTax really should make this clearer upfront - it would save so many people this stress and confusion. Thanks for sharing your experience and practical advice. This community has been incredibly helpful for navigating what seemed like a really complicated situation!

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As a newcomer to this community, I'm dealing with this exact same TurboTax Desktop situation and want to share what I've learned from reading through everyone's experiences here. I also entered summary numbers for my 1099-B instead of importing transactions (due to too many errors that seemed overwhelming to fix), and like the original poster, I only realized afterward that this might require mailing physical documents. After reading through all the helpful responses, here's what I'm taking away: **For immediate action:** Check if Form 8453 was actually generated in your TurboTax files. If it was, that form will tell you exactly what to mail and where. If it wasn't generated, you might not need to mail anything. **Key insight I missed:** Importing transactions with errors and then fixing specific problematic entries individually would have avoided the mailing requirement entirely, while still maintaining accuracy. This seems like the best approach for future years with TurboTax Desktop. **Long-term solution:** Switch back to TurboTax Online next year for the electronic document upload capability that Desktop lacks. The tools mentioned here like taxr.ai for processing investment documents and Claimyr for actually getting through to the IRS also seem worth exploring. It's reassuring to know there are practical solutions beyond just struggling with the software's limitations. Thanks to everyone who shared their experiences - this community has been incredibly helpful for understanding what initially seemed like a very confusing and stressful situation!

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Mei-Ling Chen

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Has anybody used TaxAct or TurboTax for nonprofit returns? I'm wondering if they handle these kinds of special situations or if I need specialized nonprofit tax software.

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I tried TurboTax for Business for our small nonprofit and it was honestly terrible for 990s. It's clearly designed for business returns, not nonprofits. We ended up using MyFreeTaxes which had a much better nonprofit module for simple 990-EZ filings.

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Just want to echo what others have said about documenting everything, even for that short initial period. I went through something similar with my nonprofit - we incorporated in late 2022 but didn't really start operations until 2023. For your situation, since you had zero revenue in 2023 and minimal expenses, the 990-N (e-Postcard) is probably your best bet for that first partial year (11/15/23-12/31/23). It's much simpler and you can file it online in about 10 minutes. The key eligibility factor is that your gross receipts were under $50K for that period, which they clearly were. Regarding penalties - yes, there can be late filing penalties ($20 per day up to $10K for small organizations), but the IRS is generally reasonable about waiving them for new organizations with legitimate reasons. When you file, include a statement explaining you were a newly formed organization waiting for 501(c)(3) determination and had no significant financial activity. I did this for our late first filing and never heard anything about penalties. One thing to keep in mind - make sure your fiscal year is properly established with the IRS. Since you're doing calendar year (Jan 1 - Dec 31), that should be straightforward, but double-check that it matches what you indicated in your 1023 application.

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Has anyone considered the state tax implications? Each state handles entity transitions differently. In California, for example, using an old sole prop bank account for your corp can trigger a "successor liability" issue where your corp could be responsible for any unpaid taxes from the sole prop. On the flip side, in some states incorrectly attributing income to a corporation when it should be on the sole prop could trigger minimum corporate tax requirements you otherwise might have avoided.

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This is a really complex situation that touches on several areas - entity separation, tax compliance, and banking regulations. From what I've seen in similar cases, the key is to act quickly to clean this up before it becomes a bigger problem. First, I'd strongly recommend getting that bank account ownership updated to your corporation ASAP. Most banks will let you do this with the right paperwork (corporate resolution, new signature cards, etc.). This eliminates the appearance that your sole prop is still operating. Second, you need to be very careful about how you're documenting any transfers between accounts. The IRS will want to see clear business purposes for any money movement between entities. If it looks like you're just using them interchangeably, that could jeopardize your corporate status. One thing I haven't seen mentioned yet - make sure you're not accidentally triggering any state franchise tax or minimum tax requirements by keeping the sole prop "active" through bank activity. Some states consider any business banking activity as evidence the entity is still operating, which could create ongoing tax obligations you don't need. I'd also suggest talking to a CPA who specializes in entity transitions. They can help you figure out if you need to file any forms with the IRS to properly document the transfer of assets from your sole prop to the corporation. Getting this documented properly now could save you major headaches if you ever get audited.

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StarStrider

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This is really comprehensive advice! I'm curious about the state franchise tax issue you mentioned - how would someone know if their state considers banking activity as evidence the entity is still operating? Is there a resource to check state-specific rules on this, or do you just have to call each state's tax department individually? I'm dealing with a multi-state situation and want to make sure I'm not creating problems in states where I might not even realize there are ongoing obligations.

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Jacinda Yu

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I just wanted to add my experience to help ease anyone's anxiety about this. I'm a CPA and have been helping clients navigate this exact confusion for months now. The IRS has been gradually rolling out these new portal features throughout 2024, and the "Audit Status" tab is appearing for virtually all users regardless of their actual audit status. The key thing to remember is that the IRS operates on a very structured timeline for audits. They typically have 3 years from your filing date to initiate an audit (with some exceptions), and they MUST send written notice before beginning any examination process. This isn't optional - it's required by law. Since you filed in February, received your refund in March, and haven't received any correspondence, you can be confident you're not under audit. The IRS processes over 150 million individual returns each year, and less than 1% are actually audited. The new portal tabs are just poor user experience design - they should only show relevant information to each taxpayer's situation. If you want peace of mind, keep checking your mail for the next few weeks, but based on everything you've described, you're in the clear!

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Yuki Tanaka

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This is exactly the kind of professional insight that helps so much! As someone who's never dealt with an audit before, knowing that there's actually a legal requirement for written notice makes me feel much more confident. The 3-year timeline is also helpful to understand - I had no idea they had that kind of window. It really does seem like the IRS could save everyone a lot of stress by just making these portal features more targeted to individual situations instead of showing everyone the same confusing tabs. Thanks for breaking down the actual statistics too - less than 1% being audited puts things in much better perspective!

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Natalie Wang

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I completely understand the panic you must have felt seeing that tab! I went through the exact same thing about two months ago and it really threw me for a loop. What helped me was understanding that the IRS has been rolling out these new portal features in waves, and they're appearing for everyone regardless of their actual tax situation. The fact that you already received your refund is actually the most reassuring sign possible. The IRS has automated systems that flag returns for review BEFORE they issue refunds, not after. If there had been any issues with your 2022 return, they would have held your refund while they reviewed it. I ended up calling the IRS (which took forever to get through) and the representative confirmed that these new tabs are part of their system modernization but don't indicate your personal status unless you've received official mail from them. Since you haven't gotten any letters, you're almost certainly not being audited. Try not to stress too much - the new interface is just poorly designed from a user experience standpoint. They really should only show relevant tabs instead of displaying everything to everyone!

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Malik Johnson

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Thank you so much for sharing your experience! It's really comforting to hear from someone who went through the exact same panic. I was literally losing sleep over this when I first saw that tab appear. Your point about the automated systems flagging returns BEFORE refunds makes total sense - I hadn't thought about it that way. It's such a relief to know that getting my refund in March was actually a good sign rather than something to worry about. I really appreciate you taking the time to call the IRS and share what you learned. It sounds like so many of us have been confused by this poorly designed rollout. The IRS definitely needs to work on their user experience - this tab is causing way more anxiety than it should!

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