Just a word of caution - DO NOT just keep cashing the refund checks without resolving this. The IRS operates under a "pay now, fight later" system. They might be sending you refunds now, but if they determine later that those payments were legitimately meant for your tax account, they can come back and assess underpayment penalties and interest for the taxes you should have paid. I knew someone who had a similar situation (though it was just for one year, not ongoing). They spent the refund, and two years later the IRS figured out the error and wanted not just the original amount back, but also nearly 25% more in penalties and interest.

This is such a bizarre situation! Reading through all the responses, it sounds like several people have had success getting to the bottom of similar mysteries. The fact that these payments have been so consistent for 5 years really does suggest it's not just a random error. I'd recommend trying multiple approaches simultaneously: 1) Use one of the callback services mentioned to get through to the IRS research department, 2) Have direct conversations with anyone who might have your SSN (family, former employers, accountants you've used), and 3) Consider requesting a meeting with the Taxpayer Advocate Service if the regular channels don't work. The specific dollar amounts you mentioned ($1,876.42 type numbers) really do sound like they're calculated based on something - maybe estimated taxes for a business entity, investment income, or contract work that's being reported under your SSN. Whatever you do, don't just ignore this or assume it will work out in your favor. As others have pointed out, the IRS can come back years later demanding repayment with penalties and interest if they determine these were legitimate tax obligations. Better to spend some time now getting it resolved than potentially facing a much bigger headache down the road.

One more thing to consider - if any of your non-covered securities were acquired through inheritance or gifts, the cost basis rules are different. For inherited securities, you generally get a stepped-up basis to the fair market value on the date of death. For gifted securities, it's more complicated and depends on whether the value went up or down since the original owner purchased them. If this applies to you, make sure you're using the correct basis method when entering these in FreeTaxUSA. The basis Morgan Stanley provides might not account for these special situations.

This is such a helpful thread! I'm dealing with a similar situation with Charles Schwab non-covered securities. One thing I'll add is that if you have wash sale adjustments on your non-covered securities, make sure those are properly reflected when you enter each transaction. My broker statement showed several wash sale loss disallowances that I initially missed when manually entering transactions. The IRS won't see these adjustments since the basis isn't reported to them, but you still need to account for them properly to avoid claiming losses you're not entitled to. FreeTaxUSA has specific fields for wash sale adjustments when you're entering individual transactions, so don't forget to check for those on your 1099-B!

Does anyone know if Sprintax specifically has a bulk import option for Fidelity? I'm in the same boat but with about 15 transactions, and I really don't want to enter them all manually if I don't have to.

For your specific situation with just 2 stock sales and a $0.26 loss, I'd recommend entering them separately to be completely compliant. Since it's only 2 transactions, the extra work is minimal compared to the peace of mind. However, I want to address something important that others touched on - Sprintax is generally designed for non-resident tax filing and may not be the best choice if you're a U.S. resident with investment income. Most major tax software like TurboTax, FreeTaxUSA, or H&R Block have much better investment reporting features including direct imports from Fidelity. If you're stuck with Sprintax for other reasons, you'll likely need to enter each transaction manually with the sale date, purchase date, proceeds, and cost basis for each stock. Make sure the total matches exactly what's on your 1099-B to avoid any automated matching issues with the IRS. The $0.26 loss will carry forward to future years if you can't use it this year, so it's worth reporting correctly even though the amount is small.

Just a heads up that if you refinanced last year, you might have TWO 1098 forms - one from each lender. Don't forget to add both when calculating your total mortgage interest! I almost missed this and would have underreported by $3,200.

Another thing to watch out for - if you paid any points when you got your mortgage, those should show up in Box 6 of your 1098. Points paid on a purchase mortgage are generally fully deductible in the year you bought the house, which could add a nice chunk to your itemized deductions. Since you bought in August, you might have paid origination points that you can deduct this year. Just make sure you didn't already deduct them if they were rolled into your mortgage amount rather than paid separately at closing.

Has anyone here actually calculated how many trades you need to qualify for trader tax status? I've heard different numbers from different accountants.

Just to add some clarity on the IRA question - your beneficiary IRA distributions will be taxed as ordinary income regardless of your trader status election. This is because IRAs don't have capital gains treatment to begin with. When you take distributions from a traditional IRA (including inherited ones), it's all ordinary income tax regardless of what investments were inside or how long they were held. So making the trader tax status election for your trading account won't make your IRA distributions any worse tax-wise - they were already going to be ordinary income. The election only affects your non-retirement trading account where you'd be giving up potential long-term capital gains treatment in exchange for the trader benefits like avoiding wash sales. Make sure you can handle losing long-term capital gains rates on any positions you might hold longer in your trading account before making this election.