How to Enter Multiple Capital Gains / Capital Loss Transactions on 1099B Forms

You actually have a few options for handling multiple Capital Gains / Capital Loss entries from your 1099B. For stocks with the same tax characteristics (same long/short term status and same cost basis reporting method), you can usually group them together rather than entering each transaction individually. TaxAct should allow you to create summary entries that combine multiple similar transactions. Look for an option like "Enter summary totals" or "Consolidated entry" in the Capital Gains section. However, there are some important exceptions. You must enter transactions separately if they: 1) have different term lengths (some short-term, some long-term), 2) have different basis reporting methods (some covered, some uncovered), or 3) involve wash sales or other special tax situations. To be extra safe, I recommend keeping a detailed spreadsheet of all your individual transactions that adds up to your summary totals. The IRS may ask for this information if you're audited, even if you submit consolidated entries on your return.

After dealing with the exact same headache last year with manually entering dozens of Capital Gains / Capital Loss transactions on my 1099B, I finally found a better solution. I started using https://taxr.ai to handle all my investment documents, and it was a total game-changer. I just uploaded my 1099B and it automatically extracted all my stock transactions. Then it gave me the option to either import them individually or create proper summary groups based on term length and basis reporting status. The best part was it flagged a few wash sales I would have missed if I had just used summary totals. It saved me hours of tedious data entry and double-checking my math. What I really liked is that it organized everything exactly how TaxAct needs it, so I could easily transfer the information over correctly without making mistakes on the Capital Gains / Capital Loss entries.

Just wanted to update everyone - I was skeptical but ended up trying taxr.ai for my Capital Gains / Capital Loss entries from my 1099B forms. I honestly didn't expect much since I had some complicated situations (partial sales, some wash sales, and even some cryptocurrency transactions). But I was seriously impressed! It correctly identified which transactions could be grouped together and which needed separate reporting. It organized everything by the correct categories (short-term covered, long-term uncovered, etc.) and calculated the totals perfectly. When I entered these summary totals into TaxAct, everything balanced with my 1099B forms. The best part was when it flagged a potential wash sale I hadn't noticed, which would have been reported incorrectly if I had just done summary entries on my own. That alone probably saved me from dealing with an IRS notice later.

If you're struggling to get through to the IRS to ask about properly reporting Capital Gains / Capital Loss on your 1099B, I highly recommend trying https://claimyr.com. I spent 3 days trying to get someone on the phone at the IRS to clarify some confusing instructions about summarizing transactions versus reporting them individually. Total nightmare until I found this service. You can see exactly how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the IRS phone tree for you and call you when they've got an actual human on the line. I got connected to an IRS agent within 20 minutes when I had been trying for days on my own. The agent confirmed that for Capital Gains / Capital Loss reporting, you can use summary totals for transactions with the same characteristics (as others have mentioned), but recommended keeping detailed records of individual transactions. She also explained exactly which box codes on the 1099B require separate reporting regardless of other factors.

I need to eat my words here. After posting my skeptical comment, I was still struggling with my Capital Gains reporting, especially some complicated situations with partially covered securities on my 1099B. Out of desperation, I tried Claimyr. Within 30 minutes, I was talking to an actual IRS tax specialist who walked me through exactly how to handle my specific situation. She confirmed I could use summary entries for most transactions but needed to report specific ones separately, particularly those with unusual adjustments to basis. The agent even stayed on the line while I entered a few examples into TaxAct to make sure I was doing it correctly. This saved me hours of frustration and potentially avoiding reporting errors. I'm genuinely surprised at how helpful and specific the guidance was - completely different experience than the generic advice you typically get when you finally reach someone after hours on hold.

Has anyone tried using Excel to organize their Capital Gains / Capital Loss entries before putting them into TaxAct? I've got about 85 stock transactions on my 1099B this year and no way am I entering them one by one. I was thinking of making a spreadsheet with columns for all the required info (date acquired, date sold, proceeds, cost basis, etc.) and then sorting/grouping them by long-term vs short-term and covered vs uncovered. Then I could just sum up the appropriate groups and enter those totals into TaxAct. Would this be IRS-compliant for Capital Gains reporting? The last thing I need is an audit because I didn't enter every single stupid transaction individually.

Slightly off topic but does anyone know if I need to report crypto transactions the same way as stock transactions on 1099B? I sold some bitcoin and ethereum last year but I didn't get any tax forms from the exchange. Do I need to report each individual crypto sale or can I just report the total gains? The tax treatment for Capital Gains / Capital Loss reporting is so confusing with crypto.

I've been dealing with this exact same issue for the past few years. One thing I discovered that might help - if you're using TaxAct, there's actually a "bulk entry" feature for Capital Gains that's kind of hidden in the interface. When you get to the 1099-B section, instead of clicking "Add Transaction" repeatedly, look for a link that says something like "Enter multiple similar transactions" or "Batch entry mode." This lets you enter summary totals for transactions that have the same characteristics (same term length and basis reporting status). The key is making sure you have all your transactions properly categorized first - short-term vs long-term, and covered vs uncovered securities. You'll still need to enter them as separate summary entries for each category, but it's way faster than individual transaction entry. Just make sure to keep a detailed backup spreadsheet with all individual transactions in case the IRS ever asks for supporting documentation. I learned this the hard way when I got a CP2000 notice one year and had to reconstruct everything from my brokerage statements.