Question about Form 2439 for REIT investments -- do I need this for my REITs from last year?

Thanks for explaining! Does this mean the undistributed gains on a 2439 are different from the capital gains distributions that show up on my 1099-DIV? I have both short and long-term capital gains listed on my 1099-DIV from Fidelity. Also, if for some weird reason I was supposed to get a 2439 but didn't, would the IRS flag this later?

Yes, they are different. The capital gains on your 1099-DIV are distributions actually paid out to you. Form 2439 reports undistributed gains - money the REIT earned but retained rather than distributing, yet still had to pay taxes on. As a shareholder, you get credit for those taxes paid. You don't need to worry about the IRS flagging anything. If a REIT was required to issue you a Form 2439, they would have sent it and also filed a copy with the IRS. Since you didn't receive one, it's almost certain you don't have one. REITs typically distribute most of their income to avoid corporate-level taxation, so Form 2439 situations are relatively uncommon.

How does this actually work? Do you just upload your docs and it tells you what forms are missing? I've got investments scattered across like 4 different platforms and honestly have no idea if I'm getting all the right forms.

Sounds convenient but I'm skeptical. Don't these tax prep services already check for missing forms? I use H&R Block and figured they'd catch that sort of thing. Is this actually finding stuff that the regular tax software misses?

You upload your investment documents - statements, 1099s, whatever you have - and it analyzes everything to identify specific tax situations. It compares what you have against what forms you should have based on your investment types. For my REITs across multiple accounts, it flagged exactly which investments might generate less common forms like 2439. This is different from regular tax prep software because it focuses specifically on analyzing documents and identifying missing forms before you even start inputting data. Regular tax software asks you questions but doesn't proactively scan your documents to tell you what might be missing. This catches situations where you don't even know what to look for, which was exactly my problem with the specialty REIT investments.

How does this actually work? Do you just give them your number and they call you? Seems sketchy to have some third party service involved in calling the IRS.

Yeah right, like the IRS would ever confirm whether they have forms filed under your SSN over the phone. I've called them before and they refuse to give any specific info without going through a whole verification process and even then they're super limited in what they'll tell you. I'm calling BS on this service.

You enter your phone number on their website, and they navigate the IRS phone system for you. When an IRS agent picks up, they connect the call to your phone. There's no third party on the actual call - it's just you talking directly with the IRS agent. They're simply holding your place in line so you don't have to listen to hold music for hours. Regarding verification - of course there's a verification process. When the IRS agent comes on the line, you have to verify your identity by providing your SSN, name, address, etc. Only after proper verification will they discuss your tax information. The agent I spoke with was able to check their systems and tell me they had no record of Form 2439s being filed under my SSN for that tax year, which was exactly the confirmation I needed.

Thank you for sharing your experience! That makes me feel a lot better about just selecting "no" on the TurboTax question. I was worried I was missing something major. My REITs are all pretty standard ones - nothing exotic or specialized. So if you've only gotten a 2439 once in 5 years with what sounds like a wider range of REIT investments, I'm probably fine.

You're welcome! Yes, for standard REITs, you'll typically just get the standard 1099-DIV reporting your dividends, which often includes a breakdown of ordinary dividends, qualified dividends, and capital gain distributions. The 2439 form is for a specific situation that's not common for most REIT investors. If you do have any concerns in the future, you can always contact your brokerage directly. Fidelity's tax document support is actually pretty good compared to some other platforms. They can usually confirm exactly which forms were generated for your account.

Would you have to pay additional taxes when you got those 2439 forms? I'm wondering if answering "no" when you should have said "yes" would result in underpaying taxes or if it's more of a credit situation where you'd be missing out on money back.

That's really helpful! Is the Wage and Income Transcript something I could still get now before filing? And do you know how long it takes to get it if I request it today? My tax deadline is coming up pretty soon.

If you create an account on the IRS website (irs.gov), you can access your Wage and Income Transcript immediately online. The electronic version is available for the previous tax year by late May or June, but we're still early in the filing season, so the 2023 information might not be complete yet. If you request it via Form 4506-T by mail, it typically takes 5-10 business days after they receive your request. Given the filing deadline approaching, the online method would be much faster if you qualify for online access. You'll need to verify your identity through their secure access process, which requires a financial account number or a mobile phone in your name.