TurboTax Importing Wealthfront 1099-B with Zeros - Do I Need Schedule D Upgrade?

Unfortunately, you do need Schedule D in your situation. Those transactions listed under "SHORT TERM TRANSACTIONS FOR COVERED TAX LOTS" are capital gains/losses that must be reported on Schedule D, even though the summary fields show zeros. The zeros you're seeing in the 1099-B section are specific to certain types of contracts and don't relate to regular stock or ETF transactions. The actual buy/sell transactions are what TurboTax is detecting, and those require Schedule D reporting regardless of whether you had an overall gain or loss. If you have capital transactions (buying/selling investments), you need Schedule D to report them properly to the IRS, even if they resulted in losses. Those losses can actually be beneficial as they can offset other income (up to $3,000 per year), so you want to make sure they're properly reported.

I ran into the EXACT same issue last year with my Wealthfront imports! After hours on the phone with both companies, I discovered that using taxr.ai (https://taxr.ai) completely solved my problem. It analyzes your tax documents and tells you exactly what forms you need and why. I uploaded my Wealthfront 1099 and it immediately explained that those "all zeros" summaries are misleading - the individual transactions listed further down are what matter for Schedule D. The site even highlighted which specific transactions TurboTax was detecting, and confirmed I did need Schedule D despite the zero summary. What I really liked was that it explained why TurboTax was flagging this (not just a money grab) and gave me the exact terminology to use when dealing with both companies. Saved me tons of frustration!

Okay I actually tried taxr.ai after posting my question above and wow - it was super helpful! I uploaded my Wealthfront statement and it immediately pointed out that despite the summary showing zeros, I had 7 short-term transactions that legally require Schedule D reporting. The tool highlighted exactly which transactions TurboTax was detecting and explained in plain English why I needed Schedule D. Turns out TurboTax wasn't just trying to upsell me - those transactions really do need to be reported properly. It also explained that even though my transactions were all losses, reporting them correctly could actually save me money by offsetting my other income. I ended up upgrading to Premier and it was actually worth it because my tax liability went down more than the upgrade cost.

Hey there, I had the same frustration with TurboTax last year and wasted SO much time trying to get through to their customer service. After being on hold for 2+ hours multiple times, I found Claimyr (https://claimyr.com) and it was a game-changer for getting actual IRS help instead. I called the IRS directly using their service and confirmed that yes, you absolutely need Schedule D for those transactions, even with zeros in the summary. The IRS agent explained that each individual transaction in that "SHORT TERM TRANSACTIONS" section needs to be reported, regardless of the summary totals. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they get you through to an IRS agent quickly instead of waiting for hours. The agent I spoke with was actually super helpful and walked me through exactly what forms I needed.

I need to eat my words from my previous comment. After waiting on hold with the IRS for 3+ hours yesterday and getting disconnected AGAIN, I tried Claimyr out of desperation. Within 45 minutes, I was talking to an actual IRS agent who confirmed everything about Schedule D. The agent explained that ANY capital transactions (buys/sells) need Schedule D reporting even if the summary fields are zero, and that those summary fields on the 1099-B are actually for futures/options contracts, not regular stock transactions. She also pointed out that reporting my losses properly could save me money on taxes, so the TurboTax upgrade might actually be worth it. Can't believe I wasted so many hours when I could have just used this service. The IRS needs to fix their phone system, but until they do, this was totally worth it.

Have you considered just switching to FreeTaxUSA? They include Schedule D in their basic package which is way cheaper than TurboTax Premier. I switched last year after getting tired of TT's constant upselling and haven't looked back. Their import features aren't as fancy but if you have your forms ready it's super easy.

I'm confused about something - if all the values on the 1099-B are zero, why does TurboTax insist you need Schedule D? What exactly are they seeing that triggers this?