This is a problem for your accountant :)

People learn this the hard way. These companies that pay you in 50% stock should probably have some checkbox on the employment agreement that says "I agree to get a licensed accountant to do my taxes every year, and I realize that I will be paying for this out of pocket."

The most complex tax disaster I got into cost $700 to resolve, and that is a tiny tiny fraction of what they pay you in stock, so just do it.

I’m not a tax expert. but if I’m understanding the directions on Schedule D and form 8949 correctly, if everything on your 1099-B was reported to the IRS (box A or D checked) and you don’t need to make any adjustment to basis, you can just put the grand total on Schedule D, without reporting each transaction on Form 8949.

Turbo Tax seems to take this approach, at least when I filed last year.

I've never worked for a company where the cost basis for RSUs manages to be reported accurately. I've had to correct them every single time.

This isn't a small company problem either - both Google and Microsoft had this issue (though only on ESPP shares at MS)

RSU are non-covered shares, so you can't just fill out the total on schedule D (box a or d won't be checked)

You can do the above and also send the IRS a copy of your 1099-B too, along with your 1040. I don't know if you can do that and e-file.

It's worth noting that this also only works if your 1099-B from the RSU broker are correct. In the past decade, that's about a 50-50 shot for me.

I don't have to do anything, I get a single form (1099? Don't remember) per source with gains and that's it. Don't even have to send in those forms with the return anymore. Is there some number where you have to fill out stock sales?