Reply To: Dreaded Form 8949 with many trades

Home Fairmark Forum Taxation of Investments Dreaded Form 8949 with many trades Reply To: Dreaded Form 8949 with many trades


Thanks a ton for answering me in clear details, Kaye! Thank you for your time!

Is it just electronic filing you want to avoid? Or also using software to prepare your return?

Both! The reason is I am diligent in keeping detailed record on my spreadsheet so that I know & understand every part of my transactions. Also, for electronic filing and software, it’s likely to encounter problems such as now knowing which figure to enter for a specific entry, or which choice to make among several. You have to make yes/no, black/white decisions for every entry even when you aren’t sure. You can’t write explanations or add entries.

Back to the problem:

It turns out I was comparing only the Box A in my spreadsheet with the combined Boxes A and B in the 1099-B. I just checked again, and actually my Box A and 1099 for Box A has only a discrepancy of less than $20! I know my spreadsheet that doesn’t account for wash sales should show more gains than on the form 1099, but it seems somehow some of those “wash sales” were only “transient” (e.g. Bought several lots, then sold some shares at a price that is lower than some of the purchase prices within 30 days of buying other shares, and eventually sold all the remaining shares. So maybe some shares were regarded by the system as “wash”, but ultimately it didn’t matter?). So somehow, the total result of the form 1099 is almost the same as my spreadsheet, with only less than $20 more than mine. (I did verify that all the parts with discrepancies are ones with a “W” [wash sale] printed next to them.)

There are a couple of “undetermined term” amounts of less than $5 for a certain ETF, which I have no idea what they are (they aren’t from my transactions, and are all dated the first day of a month). Since I held the ETF short term, I suppose they belong to short term?

but they also have better things to do than bother taxpayers who appear to be paying more than necessary.

I wonder if some IRS staff is annoyed by paper filings. I recently got an IRS letter about my 2018 tax return that says I owe some taxes. But their calculation was unbelievably ignorant and wrong. They used a cost basis for the gain. After I pointed out their mistake, they sent me a reply, not admitting their mistake, but simply says they needed to process “all your information” before resolving the matter. It seems as if they just wanted to find fault with me without basis. I wonder if it’s because they didn’t like my always filing paper return and attaching my own spreadsheet.

Many thanks again!