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Chris Elmeda

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Hey Ruby! Welcome to the trading world - I was in almost the exact same situation last year when I started. You're absolutely right that you'll only pay taxes on your net profit of $550 ($800 gains minus $250 losses). One thing I wish someone had told me early on is to keep really detailed records throughout the year, not just rely on your brokerage statements at tax time. I started using a simple spreadsheet to track each trade with the date, symbol, buy price, sell price, and whether it was a gain or loss. Makes tax season so much easier! Also, since you mentioned learning your lesson on penny stocks - been there! Those volatile moves can really teach you about risk management the hard way. The silver lining is that those losses do help offset your gains tax-wise, so at least there's that small consolation. Your brokerage should send you a 1099-B form early next year that will list all your transactions. Most tax software can import this directly, which saves you from manually entering every single trade. Good luck with the rest of your trading year!

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Lauren Zeb

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Great advice about keeping detailed records! I'm just starting out with trading too and wondering - do you recommend any specific apps or tools for tracking trades beyond just a basic spreadsheet? I've been manually entering everything but I'm already getting overwhelmed with just a month of data.

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Mason Stone

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Ruby, you've gotten some great explanations here! Just to add one more perspective - I'm a CPA and see this exact scenario all the time with new traders. You're absolutely correct that your $250 in losses will offset your $800 in gains, so you'll only owe taxes on the $550 net profit. One thing to keep in mind is that since all your trades were held for less than a year, they're all short-term capital gains/losses, which means they'll be taxed at your ordinary income tax rate (not the lower long-term capital gains rates). So depending on your tax bracket, you could be looking at anywhere from 10% to 37% tax on that $550. Also, don't forget about the wash sale rule - if you sold any stocks at a loss and then bought the same or "substantially identical" securities within 30 days before or after the sale, those losses might be disallowed. Your brokerage should flag these on your 1099-B, but it's good to be aware of. Keep those trading records organized and consider using tax software that can handle investment transactions - it'll make your life much easier come tax time!

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Zara Perez

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This is really helpful, especially the point about short-term vs long-term rates! I had no idea that holding period affected the tax rate so much. Quick question - is there a minimum threshold for reporting trading gains? Like if someone only made $50 in profit for the year, do they still need to report it and pay taxes on it, or is there some kind of de minimis exception for small amounts?

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Amara Torres

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Just to add to the confusion on 1098-T forms: the school isn't always correct either! Last year my daughter's college sent a corrected 1098-T in April (after I'd already filed) because they had reported some amounts incorrectly. It's worth double-checking with your school's financial aid office if something seems off about the form. For box 4 specifically, you can ask them to provide details about exactly what was adjusted and why. This might help you determine how to report it correctly, especially if you're using tax software like TaxAct.

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I went through something very similar last year! The key thing to understand is that Box 4 adjustments don't necessarily mean you owe more taxes - it depends on what education credits you claimed previously. In TaxAct, when you get to the Education section, make sure you enter the Box 4 amount exactly as shown on your 1098-T. The software will ask you about prior year education credits and calculate any recapture automatically. Since your adjustment was due to a residency status change (reducing your tuition from out-of-state to in-state rates), this is actually pretty straightforward. One thing that helped me was printing out my prior year return before entering the new 1098-T information, so I could see exactly which education credit I had claimed and for how much. This made it easier to verify that TaxAct was handling the adjustment correctly. Don't stress too much about it - these adjustments are more common than you'd think, especially with state residency changes!

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This is really helpful advice! I'm curious - when you printed out your prior year return, did you find any discrepancies between what you claimed and what the school was adjusting? I'm worried that my situation might be more complicated because I also had some scholarship money that changed when my residency status was corrected. Did TaxAct handle multiple adjustments at once for you, or did you have to enter them separately?

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This thread has been incredibly helpful! I've been on an installment plan for about 4 months now and was getting anxious about not receiving any kind of statement or confirmation beyond the initial setup paperwork. Reading about the CP89 notices coming in January/February puts my mind at ease - at least I know what to expect and when. I'm definitely going to try the automated phone line at 1-800-829-1040 that several people mentioned. The idea of getting a balance update in just a few minutes without dealing with hold times sounds amazing. I'm also taking everyone's advice about keeping detailed records. Starting this month, I'm going to save my bank statements and take monthly screenshots of my online account (once I finally get it set up properly). After hearing about payment discrepancies, it's clear that having your own documentation is crucial when dealing with the IRS. Thanks to everyone who shared their experiences - this is exactly the kind of real-world advice you can't find in the official IRS publications!

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So glad this thread has been helpful for you too! I'm also relatively new to installment plans (about 6 months in) and was feeling pretty lost about tracking my progress. The anxiety about not knowing exactly where you stand with your payments is real - especially when you're dealing with the IRS. I tried the automated phone line yesterday after reading about it here and it worked perfectly. Got my current balance in under 3 minutes, no hold time at all. Definitely saving that number for monthly check-ins while I work on getting the online account sorted out. The record-keeping advice from everyone is spot on. I started a simple spreadsheet this week to track my monthly payments alongside screenshots from my bank account. Figure it's better to be overly documented than caught off guard later if there are any issues. Good luck with your payment plan!

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Liam Murphy

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This is such a timely thread for me! I just started my installment plan about 2 months ago and have been wondering the exact same thing about statements. It's really reassuring to know that the CP89 notices come out annually in January/February - I was starting to worry that I'd never get any official documentation of my payments. I'm definitely going to try that automated phone line at 1-800-829-1040 that everyone's mentioned. Being able to get a balance update in just a few minutes without waiting on hold sounds like a game-changer. I made the mistake of trying to call the regular IRS line once and gave up after 90 minutes on hold. The advice about keeping bank statements and taking screenshots is gold. I've been pretty casual about record-keeping so far, but after reading about payment discrepancies, I'm going to start being much more diligent. Better to have too much documentation than not enough when it comes to the IRS! Thanks to everyone who shared their experiences - this kind of practical advice from people who've actually been through it is invaluable.

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You're absolutely right about being proactive with record-keeping! I learned this lesson the hard way when I first started my plan. One thing I'd add is to also keep a copy of your original installment agreement paperwork in the same place as your monthly records. I had to reference mine recently when there was confusion about my payment due date, and having it easily accessible saved me a lot of stress. The automated phone line really is a lifesaver - I use it monthly now just to double-check that my payments are being processed correctly. It's become part of my routine to call around the same time I check my bank statement each month. Takes less time than brewing a cup of coffee and gives you instant peace of mind!

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Got a 1099-MISC for reimbursed umpire fees that I paid - accountant says it's ridiculous. Am I right to be concerned?

I've been volunteering as a coach for my local youth baseball league this past year. Part of my role has been paying the umpires after each game from my personal funds, then getting reimbursed by the town later. I've been super careful about tracking every dollar - who got paid, when, and how much. Well, tax season rolls around and I just got a 1099-MISC from the town for the ENTIRE amount they reimbursed me for the umpire payments (about $3,200). When I showed it to my accountant, he practically blew a gasket and said this was "absolutely ridiculous" because these weren't actual earnings - just pass-through expenses where I was essentially acting as the middleman. I'm completely confused about this whole situation: - Why would the town issue a 1099-MISC for money that was just reimbursing me for expenses I paid on their behalf? - My accountant seems pretty adamant that this isn't proper - is he right about this being handled incorrectly? - What should my next steps be? Contact the town treasurer? File something with my taxes explaining this isn't income? - Has anyone else dealt with something similar when volunteering and handling reimbursed expenses? The town's finance office just gave me a vague response saying "this is how we handle these payments" which wasn't helpful at all. I'm worried about either paying taxes on money that wasn't actually income or getting in trouble for not reporting it correctly. Any advice?

Libby Hassan

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Has anyone considered that maybe the town is doing this on purpose? Our little league had the same issue and it turned out the town was trying to shift their tax burden by making volunteers responsible for reporting payments to contractors (the umpires). If you pay the umpires directly, TECHNICALLY you might be responsible for issuing them 1099s if they earned over $600 each, not the town. By giving you a 1099 for the total, they're putting you in a position where you either accept it as income (wrong) or you have to document that you paid it out (potentially making you responsible for the umpire 1099s).

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That's a devious but plausible theory. I work in municipal finance (not for OP's town) and I've seen some sketchy practices. If the town is properly documenting these as reimbursements, they should still be responsible for the 1099s to the umpires. OP, did you have the umpires fill out W-9 forms? If not, and if they were paid more than $600 individually, this could get complicated. The town might be trying to avoid backup withholding requirements.

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I dealt with this exact situation two years ago when I was treasurer for our local soccer league. The city issued me a 1099-MISC for $4,800 in referee reimbursements, and I was furious because I knew it wasn't income. Your accountant is absolutely correct - this is improper handling by the town. Reimbursed expenses are not taxable income to you. The IRS is very clear about this in Publication 463. Here's what I did that worked: 1. I documented every single payment to referees with receipts, dates, and amounts 2. I wrote a formal letter to the city finance department citing IRS regulations and requesting a corrected 1099 3. When they refused (which they did initially), I reported the 1099 income on my tax return but offset it completely with the documented expenses The key is having bulletproof documentation. Keep copies of every check you wrote to umpires, every reimbursement request you submitted, and any correspondence with the town about these payments. Don't let them bully you into accepting this as taxable income. You were essentially acting as their unpaid administrative assistant, not earning income. The fact that they're giving you vague responses about "how they handle these payments" suggests they either don't understand tax law or they're trying to shift their reporting burden onto volunteers. Stand your ground on this one - you're absolutely right to be concerned.

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This is exactly the kind of detailed, step-by-step guidance that's so helpful for someone dealing with this frustrating situation. Your point about having "bulletproof documentation" really resonates - I imagine that's what made the difference when you had to justify the offset on your return. Did you end up having any follow-up issues with the IRS after reporting it that way? I'm always worried about creating red flags, even when you're doing everything correctly. Also, how long did it take for the city to respond to your formal letter, and did they eventually issue the corrected 1099 or did you just have to live with the original incorrect one? It's infuriating that volunteers have to become tax experts just because municipal finance departments can't be bothered to understand the difference between income and reimbursements.

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Sasha Ivanov

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This is incredibly helpful information! I had no idea about the scholarship exception under IRC Section 530(d)(4)(B)(iii). So if I understand correctly, since my son received $3,455 in scholarships and my overwithdrawal is only $465, I can actually use this exception to avoid the 10% penalty entirely? That would mean I'd only owe regular income tax on the earnings portion (about $146 as calculated earlier) but no penalty at all. This seems like a much better option than scrambling to redeposit the $465, especially since I'm not sure if I'm still within the 60-day window. Quick question though - do I need to do anything special on my tax return to claim this scholarship exception, or does it just happen automatically when I report the overwithdrawal? I want to make sure I handle this correctly since this is my first time dealing with 529 distributions and scholarships in the same year. Thanks everyone for the detailed explanations - this community has been incredibly helpful in sorting through what seemed like a really complicated situation!

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Welcome to the community! You'll need to report this on Form 8863 (Education Credits) and potentially Form 1040 depending on how you handle it. The scholarship exception isn't automatic - you need to properly document it. When you have an overwithdrawal that qualifies for the scholarship exception, you report the taxable earnings portion as "other income" on your tax return. The IRS doesn't have a specific line for this, so many people miss it or report it incorrectly. Since this is your first time with this situation, I'd strongly recommend keeping detailed records of: 1) All qualified expenses you paid, 2) The scholarship amounts and dates received, 3) Your 529 withdrawal timing, and 4) Your calculation showing the overwithdrawal is less than the scholarship amount. The scholarship exception is legitimate but not well-known, so having solid documentation will help if you ever get questioned about it. Good luck with your taxes!

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Mia Green

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This thread has been incredibly educational! I'm dealing with a similar situation but with a twist - my daughter's school changed their tuition billing mid-year, so we have payments that crossed over between semesters. Does the timing of when qualified expenses are paid matter for the 529 coordination? For example, if I paid spring semester tuition in December but the 1098-T shows it as the following tax year, how does that affect the qualified expense calculation? Also, regarding the scholarship exception that @2545f54b5f5b Miranda mentioned - does this apply to any type of scholarship (merit, need-based, athletic) or are there restrictions on which scholarships qualify for this exception? My daughter received both a merit scholarship and a small athletic scholarship, and I want to make sure I can count both toward the exception amount. The documentation requirements @32fc3fe123ac Amelia mentioned are really important too. I've been keeping all receipts but wasn't sure exactly what records I needed to maintain for potential audit purposes. Thanks for the specific list!

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