I asked "I sold timber, but didn't get a 1099-S..." Eventually, Help offered to upgrade to TT live, but that's broken. Any ideas how to enter this, or report a bug?

Timber sales are reported in the Investment Section of TurboTax. If you're using TurboTax Online, you'll need Premier or Self-employed. 

To enter your Timber sales without a 1099-S or 1099-MISC form:

1. Open (continue) your return in TurboTax.
2. Select Pick up where I left off.
3. In the search box, search for investment sales then select the Jump to investment sales.
4. Answer Yes to the question Did you have investment income in 2022? (or Okay! to Time to kick off your investments!).
   • If you land on the Investment sales summary or Your investments and savings screen, select Add More Sales or + Add investments.
5. On the Let's import our tax info screen, select Enter a different way.
6. On the OK, let's start with one investment type screen, select Other (It doesn't matter that you don't have a 1099-S Form) then Continue.
7. Enter the requested information and Continue. 
8. Ignore The info entered should match the 1099-B from your financial institution. In the 1st drop down menu, select Land (other investment purpose).
9. Continue with the onscreen interview until complete.

For your cost basis, most people will enter a 0, but you could enter what you originally paid for the seedlings or saplings.

TurboTax doesn't support IRS Form T (Timber), but you probably don't need this form. According to the IRS, it's only needed ...when a sale or deemed sale under sections 631(a), 631(b), or other exchange has occurred during the tax year.

Thank you for letting me know about, "upgrade to TT live, but that's broken".

Do not try to find a 1099-S entry point. The sale of timber is considered a capital gain.

In TurboTax (TT), enter at:
- Federal Taxes tab (Personal in  Home & Business)

 - Wages & Income

Scroll down to:

-Investment Income

   -Stocks, mutual funds, Bonds, Other (Timber is other)

Select "No financial institution". Answer no when asked if you got a 1099-B.

Cost basis for timber is usually zero. Timber basis is not the cost of the property. 

For a discussion on Timber Basis, see https://www.extension.purdue.edu/extmedia/FNR/FNR_FAQ_2.pdf

Reference:http://www.timbertax.org/developments/Federal%20Income%20Tax%20on%20Timber-%20A%20Quick%20Guide%20for%20Woodland%20Owners.pdf

TT FAQ timber https://ttlc.intuit.com/community/entering-importing/help/where-do-i-enter-income-from-a-timber-sale/00/26620

My version of TT doesn't have "Jump to investment sales" after searching for investment sales. There's a description of selling a second home, nothing else.

You can enter this without using the Jump to tool.

• Click on the Wages & Income tab
• Next click on I'll choose what I work on
• Scroll down the screen until you come to the section Investment Income
• Chose Stocks, Mutual Funds, Bonds, Other and select Start or Update
• The first screen will ask if you sold any investments during the year, answer 
• Did you get a 1099-B or a brokerage statement for these sales? Answer No
• Tell us about this sale, Click I'll enter one sale at a time
• The drop-down boxes can be filled out with the details of the timber sale

1. Description - Timber parcel with general location or address
2. Date sold - your records
3. Date acquired - from your records
4. Sale proceeds -your records
5. Cost basis - expenses of the sale such as surveying, etc.

The timber sale will be recorded in your tax return. Here is very useful information about determining your expenses and how to determine the cost basis for a timber sale. See Pages 3 to 11.

@dbranson