Do I need Form 8949 with Schedule D for reporting long-term capital stock losses?

That's helpful, thank you! Quick follow up - when filling out Form 8949, do I need to check box A, B, or C since these were long-term losses? Also, do I need to include any special codes in column (f) since these were straightforward sales reported on my 1099-B?

For long-term transactions that are reported to the IRS on a 1099-B with basis reported to the IRS, you would check Box D on Form 8949. Long-term means you held the assets for more than a year before selling. If the information on your 1099-B is complete and accurate (showing correct basis and acquisition date) and matches what you'll report, you won't need any adjustment codes in column (f). Those codes are only used when you need to make corrections or adjustments to what was reported on the 1099-B.

How does it handle wash sales? I had a few of those this year and wasn't sure if the basis was being calculated correctly on my 1099.

Is it accurate with crypto transactions too? My broker only reports cost basis for some of my transactions but not all, so I've been manually calculating a lot of it.

It handles wash sales really well - it identifies the wash sale adjustment amounts from your 1099-B and properly accounts for them on Form 8949. It even flags when the wash sale might span across different tax years which can be tricky. For crypto transactions, it works great even with partial reporting. You can upload your crypto exchange statements, and for transactions without cost basis, it helps you calculate it using various methods (FIFO, LIFO, etc.). It then generates the proper codes in column (f) of Form 8949 to indicate when you're providing basis information that wasn't reported to the IRS.

Wait, how does this actually work? The IRS phone lines are notoriously impossible to get through. Are they just auto-dialing for you or something?

I'm skeptical. I've tried everything to get through to the IRS including calling right when they open. No way someone can reliably get me through when millions of people are calling during tax season.

It uses an automated system that navigates the IRS phone tree and waits on hold for you. When an actual IRS agent picks up, you get a call connecting you directly to them. It's basically handling all the hold time so you don't have to sit there listening to that horrible music for hours. Yes, it absolutely works even during peak tax season. Their system is constantly calling and can get through faster than individuals can. I was skeptical too but was desperate after trying for three days straight to get through about my Form 8949 questions. Got connected in about 15 minutes when I had previously wasted hours hearing "due to high call volume" messages.

Can you explain what you mean by tax loss harvesting? I'm in a similar situation with about $8K in losses this year.

Tax loss harvesting means strategically selling investments that have declined in value to realize losses that can offset capital gains or up to $3,000 of ordinary income per year. Since you already have $8K in losses, you'll use $3K this year against ordinary income, then have $5K carrying forward. In future years, if you have investments that have appreciated significantly and you want to sell them, your carried-over losses will offset those gains, potentially reducing or eliminating the tax impact. Just be careful of the wash sale rule - don't buy substantially identical securities within 30 days before or after selling at a loss.

Learned this the hard way too. Does anyone know if turbotax carries this info forward correctly if you use them consecutive years?