TT Premier 2024 Mac, 1099-B: Box1b and 1e - cost basis entry issues

[doin_taxes]

I'm trying to enter information for a stock sale. The 1099-B, box 1b shows "Unknown". Box 1e also shows "Unknown". I have calculated a cost basis for this stock, which I purchased a number of years ago.

For box 1b, the dropdown doesn't have "Unknown", so I chose "Various (or more than one date)".

I left box 1e blank, as I can't enter letters. Then, I checked the box for "The cost basis is incorrect or missing on my 1099-B".

I unchecked the box for "I have other boxes on my 1099-B to enter", as the rest of the boxes are empty on the form.

Then, I click Continue. I select "None of these apply", and click Continue again.

The next page says "We noticed there's an issue with your cost basis...Let us know if you'd like to make any changes". So, here, I select that "I know my cost basis and need to make an adjustment", and I enter the calculated "Actual cost basis" figure.

I click Continue, then select "Yes, I acquired this entire investment more than a year before I sold it". I then click Continue again.

The app returns to the "Review your ... sales" page, with the cast basis added; however, the Gain/loss is calculated incorrectly, and the Status still says "Needs Review".

If I return to edit, the page shows the "Box 1e - Cost or other basis" box highlighted red, shows a red triangle with "Needs info.", and has both checkboxes checked again. Aarrgghh! What the heck? How do I get TT to accept my answers?

[annieland · Accepted solution]

I've been using TT for Mac desktop for decades, and I'm accustomed to the quirks, so I'll try to help again.  If you're sure you have the accurate cost basis amount, just type it on the first entry form and keep the "Cost basis is incorrect on my 1099-B" box checked.  Then when you step through it'll basically be confirming that you are sure of this holding time frame.  Since you have no acquisition date reported, if you're sure that every share you sold (including any reinvestments) are all from over a year ago, reaffirm that it's a long term gain.

Then if TT makes you do a loop-dee-loop just fix what it "forgot" as far as the cost basis you entered and the 'Various' as the date and step through again to confirm.  It should stick.  It's basically just entering it on your Form 8949 as an "E" type sale which is a long-term transaction where no cost-basis was reported by the broker.  As long as you have your own record for your purchase(s) you're good to go.

[doin_taxes]

The top of the page says "Your info should match your 1099-B exactly." This won't be a problem since Box 1e actually says "Unknown" on the 1099-B?

I've also been using TurboTax for decades, but only once before have I had this many technical issues. Years ago, the app had a problem with Macs that were case-sensitive. I had to wipe my Mac and re-install OS X as case-insensitive, just to use TurboTax. Getting stuck in loops and having to play games with my entries to get the app to accept it doesn't exactly fill me with confidence that my final forms will be correct. (I always eyeball them to make sure, anyway, but still...)