Why hasn't Vanguard sent my 1099-DIV and 1099-B forms yet? Missing tax documents for dividends and capital losses

4 This definitely sounds unusual. Vanguard should provide 1099-DIV forms for dividend income over $10 and 1099-B forms for any sales of securities, regardless of whether you had gains or losses. A few things to check: First, make sure you're looking in the right place on their website - sometimes tax forms are in a separate section from regular statements. Second, verify the forms aren't just listed under a different tax year by mistake. Third, check if you selected electronic delivery for tax documents (if you did, you wouldn't receive paper copies). If none of those explain it, you should definitely contact Vanguard directly. The deadline for brokerages to issue 1099-B forms is February 15th (though they can request extensions). Some firms delay sending forms if they're waiting on final information from certain investments, but they should still communicate this to you.

12 I had the exact same problem with Vanguard last year! After hours of being stuck on hold with their customer service (which has gotten terrible lately), I finally found an easier solution with taxr.ai (https://taxr.ai). They have this document analyzer that helped me figure out exactly what was missing and what I needed to request from Vanguard. The really helpful thing was that taxr.ai showed me how to properly report the dividend income and capital losses even while I was waiting for the official forms. Their system pulled the quarterly statements from my account and extracted all the transaction data I needed. Saved me from having to file an extension! They even prepared a letter template I could send to Vanguard requesting the missing forms.

15 Just wanted to update that I tried taxr.ai after seeing the recommendation here and it was super helpful! I uploaded my Vanguard quarterly statements and it extracted all my dividend payments and stock sales perfectly. It even calculated my total capital losses correctly and showed me exactly how to report everything on my tax return. I still plan to get the official forms from Vanguard, but this at least lets me work on my tax return now instead of waiting. The document analyzer found a couple dividend payments I had completely forgotten about too. Definitely recommend for anyone dealing with missing 1099 forms!

9 After dealing with similar issues (not with Vanguard but with another brokerage), I found that calling them directly was a complete nightmare. Spent over 2 hours on hold only to be disconnected twice. Finally used Claimyr (https://claimyr.com) which got me connected to a Vanguard rep in under 10 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The Vanguard representative explained that there was a processing delay affecting accounts with specific types of investments. In my case, they had to recalculate some basis information for ETFs that had corporate actions. They were able to expedite my forms once I actually got through to them. Might be worth trying instead of waiting on hold forever.

18 I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I figured I'd try calling Vanguard directly to prove my point. Spent 1.5 hours on hold, got transferred twice, and still didn't get a clear answer about my missing 1099 forms. Out of frustration, I tried Claimyr and had a Vanguard rep on the line in about 12 minutes. The representative actually found my forms - turns out they were generated but there was a glitch in my online account access that prevented them from displaying. They emailed me the forms immediately and fixed the account issue. Pretty shocking how much time I wasted trying to do this the "normal" way. Just wanted to follow up since my skepticism was completely unfounded in this case.

5 This has happened to me before with Vanguard. In my case, it was because I had some foreign stocks that required additional information from international sources, so my forms were delayed. If you have any international investments or funds with foreign holdings, that could be the issue. Another possibility is that if your dividends are all qualified dividends under a certain threshold, they might be reported differently. Have you checked if Vanguard included the information on a consolidated 1099 form instead of separate 1099-DIV and 1099-B forms?

11 I'm in the same boat with Fidelity! Did anyone actually try calling Vanguard the old-fashioned way? What number did you use? The main customer service line has kept me on hold for ages.