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If I could give 10 stars I would If I could give 10 stars I would Such an amazing service so needed during the times when EDD almost never picks up Claimyr gets me on the phone with EDD every time without fail faster. A much needed service without Claimyr I would have never received the payment I needed to support me during my postpartum recovery. Thank you so much Claimyr!
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Andre Dupont
Former tax preparer here. Health insurance premiums for retirees can be tricky. If your insurance is through a retirement plan, sometimes part might be paid with pre-tax dollars already. Make sure you're only deducting premiums you paid with after-tax dollars!
Luca Romano
•I'm fairly certain mine are all after-tax since I'm paying directly from my personal bank account each month. But is there a way to verify this for sure? The premiums went up significantly after retirement compared to when I was working.
Andre Dupont
•The significant increase you're seeing is common. While employed, employers often subsidize a large portion of premiums or you may have been paying with pre-tax dollars through a Section 125 cafeteria plan. In retirement, you're typically paying the full premium with no subsidy. You can verify by requesting a benefits statement from your former employer or the plan administrator. They should be able to confirm that your payments are being made with after-tax dollars. The statement from them would also serve as excellent documentation for your tax records in case of an audit.
Don't forget you can only claim medical expenses that exceed 7.5% of your AGI by itemizing on Schedule A. If your standard deduction is higher than your total itemized deductions would be, it might not benefit you to itemize at all.
Jamal Wilson
•This! Standard deduction for 2024 is $14,600 for single filers and $29,200 for married filing jointly. Make sure itemizing actually benefits you before going through all this documentation hassle.
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22 Don't stress too much about this. I've been freelancing for 6 years alongside my regular job. Here's my practical advice: if your freelance income is less than 10% of your total income, just increase your W-2 withholding a bit and forget about quarterlies. Way easier.
1 Is that actually legal though? Everything I've read says you have to do the quarterly thing if you have self-employment income. I really don't want to mess this up and get hit with penalties.
22 It's absolutely legal. The IRS doesn't care HOW you pay your taxes as long as you pay enough throughout the year. The law requires you to pay taxes as you earn income, but doesn't specify whether that has to be through estimated payments or withholding. If your W-2 job withholds enough to cover both your regular income AND your self-employment income, you're fulfilling the requirement. You're still paying "as you go" - just through increased withholding rather than separate quarterly payments. Many tax professionals actually recommend this approach if your self-employment income is relatively small compared to your W-2 income.
17 Does anyone know if TurboTax or H&R Block help with calculating these quarterly payments? I'm in a similar situation but don't want to pay for a separate service if my tax software can handle it.
5 TurboTax Self-Employed does have a feature for estimated tax payments, but honestly it's pretty basic. It gives you the bare minimum calculation without optimizing for your specific situation. I used it last year and still ended up overpaying by about $800.
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Sofia Peña
One thing nobody's mentioned yet - if you're filing late, consider using certified mail with return receipt if you're mailing your return. I filed late last year and my return got "lost" in processing. Having proof of when I sent it and that it was received saved me from additional penalties. If you're e-filing, make sure you save the confirmation page showing the acceptance of your return. Late returns sometimes get extra scrutiny, so having documentation of exactly when you filed can be really important if there are any questions later.
Aaron Boston
•Do you know if the IRS is still experiencing those huge processing delays like they were last year? I'm worried my late return will go into some kind of backlog and take forever to process.
Sofia Peña
•The processing delays have improved somewhat compared to last year, but they're still working through backlogs. E-filing is definitely your best bet for faster processing - paper returns are still facing significant delays. I've noticed that returns claiming certain credits seem to face longer processing times, especially Earned Income Tax Credit or Additional Child Tax Credit. If your return is straightforward, you should see faster processing even filing late.
Just want to add that if you're filing late AND you owe money, you should still file ASAP even if you can't pay the full amount. The failure-to-file penalty is much higher than the failure-to-pay penalty! For the 2024 tax year (filing in 2025), the failure-to-file penalty is 5% of your unpaid taxes for each month your return is late, up to 25%. The failure-to-pay penalty is only 0.5% per month. BIG difference!
Chloe Zhang
•This is super important advice. I learned this the hard way a few years ago when I delayed filing because I couldn't pay. Ended up with much bigger penalties than if I'd just filed and set up a payment plan right away.
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4 Just to add something important that hasn't been mentioned yet - make sure your payroll system can handle ITINs properly. When we hired our first employee with an ITIN last year, our older payroll software kept flagging it as an "invalid SSN" because it started with a 9. We had to manually override it at first, and then eventually upgraded to a newer system that properly recognizes ITINs. Worth checking with your payroll provider before you process the first paycheck to avoid headaches.
19 What payroll system did you end up using that handled ITINs well? We're using an older version of QuickBooks and I'm worried it might have the same issue.
4 We switched to Gusto and it's been handling ITINs without any problems. Most of the newer cloud-based payroll systems seem equipped for this now. QuickBooks Online also works with ITINs from what I've heard, but the older desktop versions might give you trouble. Before you switch systems though, you might want to contact QuickBooks support about your specific version - some of them can be updated or have workarounds. The key thing is making sure the system doesn't automatically reject numbers starting with 9 during validation checks.
24 One critical thing I learned when hiring someone with an ITIN - they're still subject to the same tax withholding rules as any other employee, but there are differences with FICA taxes (Social Security and Medicare). Depending on their immigration and tax residency status, some ITIN holders might be exempt from FICA taxes. Others need to have these taxes withheld just like any other employee. You'll want to confirm their specific situation and make sure your payroll is set up correctly. I made the mistake of assuming all ITIN holders were treated identically for tax purposes, and it created a mess that took months to correct. Each case can be different based on visa status, tax treaties, and residency tests.
10 How do you determine if an ITIN holder is exempt from FICA? Is there some documentation they need to provide?
Lauren Johnson
Have you looked into treating this as a loan to the company rather than a reimbursement? If you properly document it as a loan you made to your business (even after the fact), then the repayment wouldn't be taxable income to you. I did something similar when I had to cover payroll during COVID before our PPP loan came through.
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Amelia Dietrich
•That's an interesting angle I hadn't considered. How exactly would I document it as a loan at this point? We've already processed the reimbursement as a regular transfer from the business account to my personal account a few months ago.
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Lauren Johnson
•You'd need to create a promissory note between yourself and the company, with reasonable interest terms (look up the applicable federal rate for the time period), and have your board of directors (even if that's just you) approve it retroactively. Then reclassify the "reimbursement" payment as loan repayment in your books. Be aware that this approach works best if the amount was clearly definable and specific, like covering exact payroll amounts. If you've been mixing personal and business expenses regularly without clear documentation, this becomes much harder to justify. Also, don't forget to include any interest required on the loan when doing your taxes - even if you choose to forgive it, there can be tax implications.
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Jade Santiago
Did your CPA mention anything about the possibility of treating this as an investment in your company rather than a nonaccountable plan reimbursement? Adding to your basis might be another approach depending on your business structure (S-Corp, LLC, etc).
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Caleb Stone
•This is a really good point. What type of business entity do you have, OP? The tax treatment can vary significantly based on whether you're running an S-corp, C-corp, sole prop, etc.
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