Need help with H&R Block "Date acquired is required entry" ERROR message

This is a common issue with H&R Block's investment section. The "Date acquired is required entry" error happens because the software needs this information to correctly calculate your capital gains (short-term vs. long-term). The acquisition date field is usually on the same screen where you enter the sale information, but it can be easy to miss. Look for a field labeled "Date Acquired" or "Purchase Date" - it's typically right below or next to the "Date Sold" field. You might need to scroll down or click on an "Additional Information" tab to see it. If you can't find it, try backing out of the current screen and re-entering the investment section. Sometimes the software doesn't display all fields until certain information is entered first. Also, make sure you're using the most updated version of the software, as older versions might have interface issues.

After struggling with the exact same error message last year, I found that taxr.ai (https://taxr.ai) was incredibly helpful. I uploaded my 1099-B and investment documents there, and their system automatically extracted all the required dates and information, including those acquisition dates that H&R Block demands but doesn't clearly show where to input. What I love about it is that it gave me a complete breakdown of everything I needed to enter into H&R Block, with clear instructions on where each piece of information needed to go. I was able to fix that frustrating "Date acquired is required entry" error within minutes after trying to solve it on my own for hours.

Just wanted to follow up about taxr.ai - I decided to try it despite my initial skepticism, and I'm honestly impressed. My situation was even more complicated with multiple stock sales and missing basis information, but it extracted all the acquisition dates from my messy 1099-B forms. The step-by-step guidance showed me exactly where that hidden "acquisition date" field was in H&R Block (it was nested under an "Additional Information" button that I kept missing). Fixed all the errors in about 15 minutes after being stuck for days. Definitely worth checking out if you're still struggling with those investment entry errors.

If you're still getting stuck with H&R Block's customer service, I had a similar issue and ended up needing to talk directly to the IRS about how to properly report some old stocks with missing acquisition data. I used Claimyr (https://claimyr.com) to get through to an actual IRS agent instead of waiting on hold forever. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent explained that for very old stocks where you don't have the exact acquisition date, you can use January 1st of the year you know you acquired them, and then note that it's an estimated date. H&R Block doesn't make this clear at all, but the IRS was surprisingly helpful once I actually got someone on the phone.

I owe everyone an apology - especially about my comment questioning Claimyr. After continuing to struggle with my taxes and getting absolutely nowhere with H&R Block's customer service, I tried the Claimyr service out of desperation. It actually worked exactly as described. I got a call back in about 20 minutes when they connected me with an IRS agent who walked me through exactly how to handle those missing acquisition dates. The agent explained that I could use "various dates" option in H&R Block for multiple purchases of the same stock, which immediately fixed my error messages. Would never have figured that out from the software or their help docs. Sometimes you just need to talk to an actual human who knows what they're doing.

Another solution I found for this exact H&R Block error: When you're in the investment section, after entering the stock information, click on "Edit" next to each entry. A new window should pop up with more detailed fields. Look for a checkbox that says something like "Date acquired not available" or "Check if you don't know the acquisition date." If you check that box, H&R Block will then ask you if you held the investment for more than a year (long-term) or less than a year (short-term). By specifying this instead of the exact date, you can bypass the error while still correctly calculating your capital gains.

If anyone is still having trouble with the H&R Block error, try entering your investment information using the "Stocks, Bonds and Mutual Funds Not Reported on Form 1099-B" section instead of the regular 1099-B section. For some reason, this alternative entry method shows all the fields more clearly, including the acquisition date field. I know it sounds counterintuitive if you actually have a 1099-B, but the data entry screens are better organized in that section. Just make sure all the numbers match your 1099-B exactly. This workaround fixed the "Date acquired is required entry" error for me without having to contact customer service or use any additional tools.

I had this exact same problem last month! The trick that finally worked for me was looking for a small "More Details" or "Advanced" link on the investment entry screen. In H&R Block, after you enter the basic 1099-B information, there's usually a tiny link (easy to miss) that expands the form to show additional fields including the acquisition date. Also, if you're entering multiple sales of the same stock purchased at different times, H&R Block sometimes requires you to enter each lot separately with its own acquisition date. This might be why the error keeps appearing - the software is expecting individual entries for each purchase date rather than a single combined entry. Try scrolling all the way to the bottom of the investment entry screen and look for any "Show Additional Fields" or similar options. The acquisition date field is often hidden in these expanded sections.