Just a heads up - don't forget to check if your grandfather ever received dividend reinvestments on these shares. Each reinvestment would have its own cost basis and holding period, so selling all the shares at once could actually be multiple transactions from a tax perspective. Makes the paperwork more complicated but could help establish at least some basis.

Another option to consider is reaching out to the company's transfer agent directly. Most publicly traded companies use transfer agents like Computershare, AST, or EQ Shareowner Services to maintain shareholder records. Even if your grandfather's brokerage doesn't have the historical data, the transfer agent might have records of when shares were originally issued or transferred, especially if there were any stock splits or corporate actions over the years. You can usually find out who the transfer agent is by looking at the company's investor relations website or calling their main investor relations number. I've had success with this approach for some old family shares where the original purchase documentation was long gone. Also, don't overlook checking if your grandfather might have old tax returns that show dividend income from these shares. Even without the purchase records, consistent dividend reporting over many years can help establish ownership timeline and potentially support a reasonable basis estimate when combined with historical stock price research.

I went through this exact situation a couple years ago when I needed old W-2s for a background check. Here's what worked for me: First, definitely try the IRS Get Transcript service that others mentioned - it's free and official. But heads up, the identity verification can be tricky if you've moved around a lot or don't have established credit history at your current address. If that doesn't work, here's a lesser-known option: many payroll companies (like ADP, Paychex) keep records longer than individual employers do. If you remember who processed your paychecks, you can sometimes contact them directly. They'll usually need your SSN and employment dates, but don't require you to go through your old manager. Also, check if you have any old bank statements from that time period - they sometimes show the employer name on direct deposits, which can help you figure out the payroll processor if you're not sure. For the 1099s, if you remember the companies that paid you, you can often find their tax ID numbers online and request copies directly from their accounting departments. Most businesses are pretty good about providing these since they're required to keep the records anyway. The key is being persistent but also having multiple backup plans. Don't put all your eggs in one basket!

I've been following this thread and wanted to share my experience from a slightly different angle. I actually work at a small accounting firm and we help clients with these types of document recovery issues pretty regularly. One thing I haven't seen mentioned is that if you're completely stuck with the IRS online system, many local VITA (Volunteer Income Tax Assistance) sites can help you navigate the transcript request process. They're usually staffed by people who are familiar with common issues like identity verification problems, and the service is completely free. Also wanted to add that for restaurant chains like Shake Shack, their corporate payroll departments are usually pretty efficient with these requests. I've helped clients get documentation from similar chains and they typically have dedicated processes for handling former employee record requests. Much easier than trying to work through individual franchise locations. One more tip - if you end up needing to prove your employment dates or income for any reason while waiting for the IRS transcripts, your Social Security statement (which you can access online at ssa.gov) will show annual earnings by employer. It's not as detailed as a W-2, but it can serve as interim verification for some purposes. The key thing is having multiple backup plans since different approaches work better for different people depending on their specific situation. Don't get discouraged if the first method doesn't work out!

Another option if you're concerned - just call H&R Block's customer service number directly from their main website (the hrblock.com one) and ask them to verify if gethrblock.com is legitimate. That's what I did when I was in the same situation last year. They confirmed it's their official download portal for retail software purchases.

I download H&R Block every year and yes gethrblock is legit. They use different websites for different things. Kind of confusing but totally safe.

I've been dealing with ESPP tax issues for years and want to clarify a few things based on my experience. The key is understanding that when you purchase ESPP shares at a discount, that discount is typically treated as compensation income and should appear on your W-2 in the year you bought the shares (not when you sold them). If you can find your W-2 from the year you purchased the ESPP shares, look for the discount amount included in your wages. If it's there, then you should definitely use the adjusted cost basis to avoid being taxed twice on the same money. However, if for some reason the discount wasn't included in your W-2 when you purchased (which can happen with some plan structures), then you'd use the regular cost basis and pay tax on the discount as part of your capital gains. The most important thing is to use Form 8949 with the proper adjustment code when your basis differs from the 1099-B. Don't just enter a different number without explanation - that's what triggers those CP2000 notices people mentioned. I'd also recommend keeping detailed records of your ESPP purchases, including purchase dates, discount amounts, and whether those discounts were included in your W-2 income. This documentation will be invaluable if you ever need to justify your basis calculations to the IRS.

I sold employee stock shares in 2025. My 1099 B from Computershare showed the cost basis but not the adjusted cost basis. I did not receive a supplemental form. I did purchase the shares at a discount. What do I do?

One important thing about filing without 1099s - the IRS matching system won't have those earnings on file. In my experience, this can sometimes trigger a verification letter later where they ask you to confirm your income (happened to me in 2023). Don't panic if this happens - just respond with your documentation. As long as you reported everything accurately, you'll be fine. This is also why keeping good records is super important when you don't have official forms!

Great advice from everyone here! I'm a tax preparer and want to emphasize a few key points for your husband's barber income: 1. You're absolutely correct that ALL income must be reported, regardless of receiving a 1099. The $5,200 goes on Schedule C as self-employment income. 2. He'll owe self-employment tax (15.3%) on the net profit, but this also means he's earning Social Security credits. 3. Payment apps like Venmo/Cash App are required to issue 1099-K forms only if you exceed $5,000 in a calendar year (the threshold changed for 2024), so he may actually receive one next year if his income increases. 4. For TurboTax, look for "Business Income" or "Self-Employment Income" and select "Income not reported on tax forms." You'll enter the total income and can deduct legitimate business expenses. 5. Create a simple spreadsheet now tracking all 2025 income and expenses - it'll make next year's filing much easier! The fact that you're being proactive about reporting this income correctly shows you're on the right track. Keep those payment app records and any business expense receipts!