I actually used PayUSATax earlier this year and can confirm it's legitimate - they're listed as an official IRS payment processor. The process was straightforward, though I did get hit with that ~2% convenience fee others mentioned. One thing I wish I'd known beforehand: if you're considering the PayPal option, make absolutely sure you can pay it off within those 6 months. I spoke with someone who missed the deadline by just a few days and got slammed with retroactive interest on the entire amount at something like 24% APR. For what it's worth, I also ended up calling the IRS directly (eventually got through after multiple attempts) to compare their installment plan options. For my situation, their plan was actually cheaper in the long run than the PayUSATax fee, but it really depends on how much you owe and how quickly you can pay it back. The IRS direct payment option with a bank account has no fee at all if you can manage the lump sum. Just make sure whatever route you go, you keep all your confirmation receipts and check your IRS account online to verify the payment posted correctly!

I've been researching tax payment options myself and wanted to share what I've learned. PayUSATax is definitely legitimate - they're an IRS-authorized payment processor, which you can verify on the official IRS website. However, before committing to any payment plan with fees, I'd strongly recommend double-checking your tax calculations first. I've seen several people mention finding missed deductions that significantly reduced their tax bills. Even a small reduction could make the difference between needing a payment plan and being able to pay in full. If you do go with PayUSATax, just be extra careful about that PayPal 6-month promotion. The terms are strict - if you're even a day late on the full payoff, they'll charge you retroactive interest on the entire amount at credit card rates (20%+). That could end up costing you way more than just paying the IRS directly with their installment plan. For comparison shopping, the IRS's own direct payment from your bank account is free, and their installment plans typically charge a setup fee plus interest that might be lower than third-party processor fees depending on your situation. Worth getting the exact numbers before deciding. Keep all your receipts and confirmation numbers regardless of which route you choose!

Your $812 extra withholding calculation sounds about right for your income situation. With combined income of $275k, you're likely hitting the 24% or even 32% tax bracket on the higher portions of your income, but each employer's withholding system assumes their job is your only income source. Here's what's happening: when employers withhold taxes, they use tables that assume that specific job is your only income. So your wife's employer withholds as if she's making $158k total, and your employer withholds as if you're making $117k total. But your actual tax liability is based on $275k combined income, which pushes you into higher brackets. The $812 per paycheck works out to about $21k annually in extra withholding, which could very well be the difference between what your employers naturally withhold versus your actual tax liability at that income level. You absolutely can split this between both your W4s - it doesn't matter to the IRS which employer withholds the extra amount. If cash flow is a concern, splitting it might make more sense for your budget. Just make sure the total extra withholding across both jobs equals what the calculator recommended. I'd also suggest running a quick sanity check by estimating your total tax liability for the year and comparing it to what would be withheld without the extra amount. That difference should be close to your calculated extra withholding.

I went through this exact same situation last year when my wife got promoted! The $812 per paycheck does sound high, but it's probably accurate given your combined income level. One thing that helped us was using the IRS Safe Harbor rule - if you withhold at least 100% of last year's total tax liability (or 110% if your prior year AGI was over $150k), you won't owe penalties even if you end up owing some tax at filing time. This gave us peace of mind that we weren't massively over-withholding. Also, consider that you might be eligible for additional deductions or credits that could reduce your actual tax liability - things like maxing out 401k contributions, HSA contributions if available, or other pre-tax benefits that weren't factored into the basic W4 calculator. My recommendation would be to start with the calculated amount but definitely split it between both your W4s for better cash flow management. You can always adjust mid-year if it seems like too much when you see how your paychecks look.

This thread has been incredibly helpful! I was pulling my hair out over the same issue with my Schwab 1099-B. I kept seeing gain/loss calculations right there on the form but getting warnings about missing cost basis info. After reading through everyone's explanations, I finally understand that it's all about what gets reported to the IRS versus what the brokerage shows me. The key insight about checking the "Cost Basis Reported to IRS" column on the 1099-B is gold - I wish they made that more obvious! For anyone else dealing with this, I found that most of my "non-covered" transactions were from stock purchases I made back in 2009-2010 (before the reporting requirements kicked in) and some transfers from an old Merrill account. Makes total sense now why those would need code B on Form 8949 even though Schwab calculated the gains correctly on my form. One thing I'd add is that if you're using tax software, double-check that it's not automatically importing these as "covered" transactions. I caught TaxAct trying to treat everything as if it was reported to the IRS, which would have been wrong for about half my trades.

I've been dealing with this exact same confusion for years and finally have a system that works! What really helped me was creating a simple spreadsheet to track the status of each transaction before tax season even starts. Here's what I do: Every time I sell something, I immediately check Fidelity's "Positions" page to see if that security shows up as "covered" or "non-covered" for cost basis reporting. I log this in my spreadsheet along with the basic transaction details (date sold, proceeds, my calculated gain/loss). Then when my 1099-B arrives, I can quickly cross-reference my spreadsheet against the "Cost Basis Reported to IRS" column to make sure everything matches up. Any "No" entries in that column go straight to the "needs code B on Form 8949" pile. This has saved me so much stress during tax season because I'm not scrambling to figure out which transactions are causing the "missing cost basis" warnings. Plus it helps catch any discrepancies between what I calculated during the year versus what shows up on the actual 1099-B. The whole system takes maybe 5 minutes per transaction when I sell, but saves hours of confusion in March/April!

Something no one mentioned yet - if you live in a state with income tax, you'll likely owe state taxes on gambling winnings too! Each state has different rules. For example, some states allow you to deduct losses like federal, others don't. Make sure you check your specific state's rules.

One thing that might help ease your mind - the $600 threshold is just a reporting requirement, not a withholding trigger. Most sports betting platforms won't automatically withhold taxes from your winnings unless you hit much higher thresholds (usually $5,000+ and certain odds ratios). However, you're still responsible for paying taxes on ALL your gambling income when you file, regardless of whether taxes were withheld. Since you're expecting to stay under $5,000 for the year, you probably won't have automatic withholding, but you should set aside about 20-25% of your net winnings to cover federal and state taxes. Also, make sure you understand the difference between gross winnings and net winnings. You can only deduct losses up to your total winnings if you itemize deductions, so if you win $4,000 but lose $3,000, you'd pay taxes on the full $4,000 but could potentially deduct the $3,000 in losses. Keep every receipt and record!

This has been incredibly helpful! I'm new to HCSMs (just joined Medi-Share this year) and had no idea about these tax implications. One thing I'm still confused about - what happens if you receive a reimbursement in a different tax year than when you paid the medical expenses? For example, if I paid $10,000 in medical bills in December 2024 but didn't receive the HCSM reimbursement until February 2025, which tax year does this affect? Also, I noticed some people mentioned keeping spreadsheets to track everything. Does anyone have a template they'd recommend? I want to make sure I'm documenting everything correctly from the start rather than trying to piece it together later. Really appreciate everyone sharing their experiences - this is exactly the kind of practical advice you can't find in the official IRS publications!

This thread has been incredibly informative! I've been a member of Christian Care Ministry for about three years now and have been handling the tax side of things completely wrong. I've been treating my monthly shares as medical expense deductions AND claiming the full amount of my medical expenses even when they were reimbursed. Looks like I need to file some amended returns! For anyone just starting with HCSMs, I'd strongly recommend setting up your tracking system from day one. I wish I had found this discussion three years ago - would have saved me a lot of headaches and probably some penalties. One additional tip based on my experience: make sure you understand the difference between "incidents" and individual medical expenses when tracking for taxes. My HCSM groups related expenses into incidents for sharing purposes, but for tax deduction purposes, you still need to track each individual expense and whether it was reimbursed. The incident grouping can sometimes make it confusing to figure out exactly which specific expenses were covered versus not covered. Also, don't forget about things like mileage to medical appointments, prescription costs, and medical equipment - these often get overlooked but can add up to significant deductible amounts if they weren't reimbursed by your HCSM. Just make sure you're following the same rule: only deduct what you actually paid out of pocket after all reimbursements.