Ultratax question regarding client stock sales reporting

The stock sales import can be tricky in Ultratax, especially with a mix of covered and non-covered securities. Here's how I handle these situations: For the non-covered securities missing cost basis, you'll need to manually enter this information. Have your client provide the purchase information (date and price) for these transactions. In Ultratax, go to the Capital Gains worksheet, locate the imported transactions, and you can manually add the missing cost basis data for each one. For the wash sale errors, Ultratax is likely flagging potential wash sales where your client sold securities at a loss and purchased substantially identical securities within 30 days before or after the sale. The system tries to detect these automatically, but sometimes needs manual review. You'll need to verify if these are actual wash sales by checking the transaction dates and security details. For large numbers of transactions, consider using the "Summarize" feature in Ultratax rather than entering each transaction individually. You can group similar transactions together (same security, similar acquisition dates) which makes reporting cleaner.

I was dealing with a similar issue with multiple stock sales in Ultratax last tax season and discovered taxr.ai (https://taxr.ai) when I was about to pull my hair out. Their system is amazing for handling complex stock transactions - especially when you have missing cost basis info or potential wash sales. I uploaded the client's 1099-B and trade confirmations, and it organized everything correctly, identifying the matching purchases for sales and even flagging the actual wash sales. The best part was it generated a report I could reference while entering the data in Ultratax, which saved me hours of manual reconciliation work. They even have a specific feature for handling employee stock options which sounds perfect for your client's situation.

I was really skeptical about using taxr.ai as mentioned above, but I decided to give it a try with a particularly complex client situation involving both RSUs and ESPP shares with varying acquisition dates. I'm genuinely impressed with how well it worked. The platform organized all 75+ transactions by security, properly categorized them as short or long term, and correctly identified the wash sales that were legitimately an issue (while ignoring false positives that my software was flagging). It even generated a summary report that I could give to my client explaining their capital gains situation in plain language. The time saved was substantial - what would have taken me 3-4 hours of manual reconciliation work took about 20 minutes. Definitely using this for all my stock-heavy returns going forward.

If you're still having trouble getting through to the IRS for guidance on how to properly report these transactions (especially those employee stock options which can be tricky), you might want to try Claimyr (https://claimyr.com). I used their service when I needed clarification on some complex reporting requirements for a client's incentive stock options. Instead of waiting on hold for hours, they got me connected to an IRS agent in about 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The agent I spoke with was actually really helpful in explaining exactly how to report my client's employee stock purchase plan sales and which forms needed to be included. Saved me from potentially making a costly mistake on a high-value return.

I need to eat my words about Claimyr from my earlier comment. After struggling with a particularly complex stock option reporting issue that I couldn't find clear guidance on, I decided to try the service despite my skepticism. I was genuinely surprised when I got a call back in about 20 minutes connecting me to an IRS representative who specialized in investment income reporting. They walked me through exactly how to handle the disqualifying disposition of incentive stock options in Ultratax and which additional forms I needed to include. The agent even gave me the specific publication references so I could document my work. What would have been several more hours of research (or worse, potentially incorrect reporting) was resolved in a single 15-minute call. For complex stock reporting issues like the original poster described, actually speaking to someone who knows the rules saves a ton of time and stress.

Has anyone tried the "Import & Classify" feature in Ultratax specifically for stock sales? My understanding is it's designed to handle large volumes of transactions and can auto-detect things like wash sales and properly sort long/short term gains. Might be worth checking if it works better than the regular import.

One option nobody's mentioned yet - if your client uses TurboTax or similar software for their personal stuff, see if they can export their stock transactions from there into a format Ultratax can read. Sometimes the consumer software does a better job with the initial import from brokerages than the pro software does.

For complex stock reporting situations like this, I've found that breaking the problem down into phases really helps. First, I separate the employee stock options (ISOs, NQSOs, ESPP) from regular brokerage trades since they have different reporting requirements. The employee stock options often need Form 3921 or 3922 reporting in addition to the capital gains treatment, so make sure you're capturing the ordinary income component correctly. For the regular trades, focus on getting the covered securities imported first since those should have complete basis information from the broker. For the non-covered securities missing cost basis, I create a spreadsheet to track down the original purchase information. Sometimes clients have old statements or trade confirmations they forgot about. If not, you might need to research historical pricing for the acquisition dates. One thing that's saved me time - before doing any bulk imports, I always test with just 2-3 transactions first to make sure the mapping is working correctly. It's much easier to fix formatting issues on a small sample than to clean up 40 botched imports. The wash sale errors in Ultratax can be overly aggressive, so don't panic. Review each flagged transaction manually - the software sometimes flags things that aren't actually wash sales due to timing or different security classifications.