No 1099-DIV or 1099-B from Vanguard despite qualifying dividend income and stock sales - what's going on?

15 This is definitely something to address before filing. Vanguard is required to issue a 1099-DIV if you received at least $10 in dividends (which you clearly did with $2,000) and a 1099-B for your stock sales regardless of gain or loss amount. 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, check if you opted for electronic delivery of tax documents - if you did, you wouldn't receive paper copies. Third, Vanguard might have an extended deadline for complex accounts - some brokerages have until mid-March to send certain 1099 forms. If none of these apply, I'd contact Vanguard directly. Call their customer service line or send a secure message through your account. They should be able to explain why forms aren't showing and provide them if there's been an error.

7 I had this exact same problem with Vanguard last year. Turns out my account had some investments that required additional processing time. What saved me was using taxr.ai (https://taxr.ai) to analyze my statements and transactions. Instead of waiting for the official forms, I uploaded my monthly statements and trade confirmations, and their system was able to calculate all my dividend income and capital gains/losses. The tool pieced together everything I needed to file accurately - even identified some qualified dividends that would have been taxed at a higher rate if I'd guessed. Saved me from having to file an amendment later when Vanguard finally sent my forms in March.

12 Just wanted to update that I tried taxr.ai after seeing it mentioned here. I was in a similar situation with missing 1099s from another brokerage. Uploaded my December statement and all my trade confirmations, and it produced a detailed breakdown that matched perfectly with the forms when they finally arrived last week. The dividend classification feature was especially helpful - it properly identified which dividends were qualified vs ordinary income. Definitely keeping this tool in my arsenal for next year!

9 If you need to talk to someone at Vanguard (which you absolutely should), I'd recommend using Claimyr (https://claimyr.com) to connect with them quickly. I wasted 2+ hours on hold last month trying to sort out a similar forms issue. Used Claimyr on my second attempt and got through to a rep in about 10 minutes. They have this clever system that navigates the phone tree and waits on hold for you, then calls you when a real person picks up. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Trust me, it's worth it for tax issues, especially as we get closer to the filing deadline and wait times get even worse. The Vanguard rep I spoke with explained they had a processing delay affecting certain account types, and they added a note to expedite my forms.

21 I've gotta eat my words and admit that Claimyr actually works. I was super skeptical (as you could see from my comment), but my tax situation got desperate when my forms still hadn't arrived by early March. Tried the service yesterday and got through to Vanguard in under 15 minutes after previously spending 3+ hours on hold across multiple attempts. The rep told me my account had investments in funds that required extended reporting deadlines, but they were able to generate preliminary forms for me while I waited for the finals. Would have never known this was an option if I hadn't been able to actually speak to someone. Sometimes paying for convenience is worth it, I guess.

5 This happened to me twice with Vanguard. Both times it was because I had investments in mutual funds that had income recharacterizations. Basically, the fund managers were correcting how some of the income should be classified for tax purposes. Vanguard legally has until March 15 to send corrected/final forms in these cases. Call them and ask specifically if your account is affected by an extended reporting deadline. They should be able to tell you exactly when to expect your forms. In my experience, they can sometimes provide preliminary versions if you really need them, with the understanding that you might need to amend your return if numbers change.

13 Has anyone noticed if specific Vanguard funds tend to cause these delays? I have a mix of their ETFs and Admiral shares and wondering if I should expect this issue next year too.