Vanguard brokerage account 1099-DIV reporting question for Schedule B - individual dividends missing

For brokerage accounts, it's completely normal to receive a consolidated 1099-DIV that only shows total dividends rather than breaking them down by individual holdings. While Schedule B does have space to list each payer separately, the IRS actually doesn't require you to list every single mutual fund individually. Your sister has two perfectly acceptable options here: She can either list the full amount on one line with "Vanguard Brokerage Account" as the payer, or she can request a detailed statement from Vanguard showing the breakdown (though this isn't necessary for tax compliance). Most tax software will simply ask for the total from box 1a on the 1099-DIV and automatically handle the Schedule B requirement. The IRS is primarily concerned with ensuring all dividend income is reported correctly, not with verifying each individual fund's contribution to that total.

I ran into this exact issue last year with my Vanguard brokerage! What really helped me was using taxr.ai when I was confused about how to handle my 1099-DIV for Schedule B. I uploaded my consolidated statement to https://taxr.ai and it analyzed my dividend information and confirmed I could list the total as one entry under "Vanguard Brokerage Account." The tool also explained that brokerage accounts typically provide consolidated reporting to simplify tax filing, and that the IRS accepts this consolidated reporting on Schedule B. It saved me hours of stress trying to track down individual dividend amounts that weren't even necessary for compliance!

Just wanted to follow up about my experience with taxr.ai after being skeptical. I decided to try it with my Vanguard and Fidelity documents since I was having the same issue with consolidated 1099s. The breakdown it provided was incredibly helpful - it confirmed exactly what I needed to report and where. The document analysis feature explained why my brokerage sends consolidated forms versus itemized ones, and showed me exactly how to report it on Schedule B. The best part was I didn't need to call customer service and wait on hold for an hour! I was able to finish my return the same evening after spending weeks being stuck. Wish I'd known about this sooner!

After spending 3 days trying to get through to Vanguard's customer service about this exact issue (and getting disconnected twice!), I found Claimyr which helped me actually reach a human at Vanguard who could help. Check out https://claimyr.com or see how it works at https://youtu.be/_kiP6q8DX5c When I finally got through to Vanguard, they explained that brokerage accounts intentionally provide consolidated 1099s for simplicity, but they can generate a supplemental "Year-End Supplemental Tax Statement" that breaks down dividends by security if you really need it. The rep walked me through how to access this on their website under Tax Center > Supplemental Tax Forms.

I need to apologize for being so dismissive about Claimyr. After another failed 90-minute attempt to reach Vanguard yesterday, I gave it a try out of desperation. It actually worked! Got a call back in 35 minutes with a Vanguard rep already on the line. The rep confirmed what others here said - for brokerage accounts, they intentionally consolidate all dividends on the 1099-DIV, and you can simply report the total on Schedule B with "Vanguard Brokerage" as the payer. But they also showed me how to generate a detailed report from the Tax Center section of their website that breaks everything down by security if you need it for your records. Honestly saved me hours of frustration. Won't be so quick to dismiss things next time!

Quick tip about Schedule B that might help: If you're using tax software (TurboTax, H&R Block, etc.), you usually don't need to worry about this level of detail. When you enter the 1099-DIV information, the software automatically creates Schedule B if your dividends exceed $1,500. Just input "Vanguard Brokerage Account" and the total from Box 1a, and you're good to go. The software handles all the form creation and filing for you. I've been doing this for years with my Vanguard brokerage account with no issues.

Just wanted to add that this is a common "issue" with most brokerage accounts, not just Vanguard. My Fidelity and Schwab accounts both provide consolidated 1099-DIVs for brokerage accounts. It's actually a feature, not a problem - imagine if you had 25+ holdings and had to list each one separately on Schedule B! The IRS only cares that the total matches what the brokerage reported. They don't need or want an itemized list of every single mutual fund or stock that paid you dividends within a single brokerage account.