When should I expect to receive 1099 forms from my investment company? Latest deadline?

Investment companies should send most 1099s by January 31st, but there's an important exception - for brokerage accounts and investments, companies have until February 15th to send 1099-B, 1099-DIV, and 1099-INT forms. If the investments involve certain complex instruments or REITs, they can actually request an extension from the IRS and may not send forms until March 15th. Since we're already past February 15th, your brother should definitely call both companies. The old company should issue a 1099-R for the IRA for the portion of the year they held it, and the new company should issue forms for both accounts after the transfer. Sometimes when accounts transfer late in the year, there can be confusion about which firm is responsible for which forms.

I went through something similar last year when my accounts were transferred between firms. I was getting super stressed about the missing forms until I found this tool called taxr.ai (https://taxr.ai) that really helped me track everything. It basically scans all your tax documents and tells you which ones you're still missing based on what you had last year and what the IRS would expect from your investment types. The tool flagged that I was missing a 1099-R from my old brokerage for an IRA that had been transferred. Turns out they weren't going to send it automatically because they thought the new firm was handling it! The taxr.ai system caught it because it knows what forms should be generated based on account types and transactions.

I was really dubious about this taxr.ai thing at first, but I decided to try it last week when Vanguard still hadn't sent my corrected 1099. I uploaded what I had, and the system immediately flagged that I was missing a 1099-DIV from a dividend reinvestment plan I'd forgotten about, plus it spotted that my mortgage lender had sent a 1098 with an incorrect mortgage interest amount. What impressed me was how it cross-referenced the documents against each other - it noticed discrepancies between my reported dividends and what should have been reported based on my holdings. When I called the companies, they both confirmed they needed to send corrected forms! It's saved me from potentially getting a CP2000 notice from the IRS later.

If you're still missing forms and the companies are giving you the runaround, I highly recommend using Claimyr (https://claimyr.com) to actually speak with someone at the IRS. I was in the same situation last year - missing 1099s, companies blaming each other, and I couldn't file my taxes. I spent HOURS trying to get through to the IRS directly with no luck. Then I used Claimyr and they got me a callback from the IRS in about 45 minutes. The IRS agent explained exactly what forms I should expect from each company after a mid-year transfer and even contacted the companies directly to sort it out. You can see how it works here: https://youtu.be/_kiP6q8DX5c - it's basically a system that navigates the IRS phone tree for you.

I have to eat my words about Claimyr. I tried it yesterday after posting my skeptical comment, and I got a call from an actual IRS agent within an hour. The agent confirmed that for IRAs that were transferred mid-year, both the old and new custodians should issue 1099-Rs showing the transfer. She also explained that because the transfer happened after October, the old firm is responsible for all the tax forms for those accounts this year. Apparently, there's a cutoff date where responsibility switches. The IRS agent even gave me direct contact information for the department at the investment firm that handles tax reporting issues. Problem solved in one afternoon after weeks of frustration!

One thing to watch out for with transferred accounts - sometimes the forms come under different account numbers! My dad had this exact issue. Both his old and new investment companies issued forms, but the new company used temporary account numbers during the transition that were different from his final account numbers. Check your mail carefully and look at your December statements from both companies. Sometimes they'll mention the tax reporting numbers which might be different from your regular account numbers. Also ask your financial advisor to help - they should be able to contact the back office and find out exactly what's going on with the forms.

For anyone still waiting on forms, you can also request a wage and income transcript directly from the IRS after February 15th. It won't have all the details of your actual 1099s, but it will show what forms have been filed under your SSN. I do this every year as a double-check to make sure I haven't missed anything. Go to IRS.gov and search for "Get Transcript Online" - you'll need to create an account if you don't have one. The wage and income transcript shows all reported income documents filed with your SSN, which can help you identify if there are forms you haven't received yet.

Just wanted to add another perspective on this - I work in the operations department at a mid-sized investment firm, and account transfers in the fall are notorious for causing 1099 confusion. Here's what's likely happening with your brother's situation: For the IRA transfer, both firms should issue forms but they report different things. The old firm issues a 1099-R showing the distribution from their custody, and the new firm should issue a 1099-R showing the rollover contribution. If it was a direct trustee-to-trustee transfer, the old firm might not issue anything if no taxable event occurred. For the trust account, it depends on when exactly the transfer completed. If it was after November 1st, the old firm typically remains responsible for ALL the tax reporting for that year, even if the new firm held the assets for part of December. This is an industry convention to avoid duplicate reporting. I'd recommend calling both firms and asking specifically: "What 1099 forms should I expect for tax year 2024 for account [number]?" They should be able to tell you definitively whether forms are coming and when. If they say no forms are coming, ask them to put that in writing - it'll save you headaches later if the IRS comes asking.

This thread has been incredibly helpful! I'm dealing with a similar situation where my Roth IRA was transferred between firms in September, and I've been getting conflicting information from both companies about who's responsible for the 1099-R. One thing I discovered that might help others - if you have online access to both your old and new accounts, check the "Tax Center" or "Tax Documents" section on both websites. Sometimes the forms are available for download before they're mailed, and you can see if there are any pending corrections or amendments. Also, for anyone waiting on complex investment forms (like K-1s from REITs or partnerships), those can legally come as late as September 15th if the investment company files extensions. I learned this the hard way last year when I filed early and then had to amend my return three times as corrected forms kept trickling in. The IRS wage and income transcript tip from Andre is golden - I just checked mine and found a 1099-INT from a bank account I'd completely forgotten about that earned $12 in interest. It's amazing how these small forms can slip through the cracks!

This is such a comprehensive thread - thank you everyone for sharing your experiences! As someone who's been through multiple account transfers over the years, I wanted to add a few more practical tips that have saved me headaches: First, if you're dealing with transferred accounts, create a simple spreadsheet tracking what forms you received last year versus what you've gotten so far this year. This helps you spot patterns - for example, if you got a 1099-DIV from XYZ mutual fund last year but haven't seen one yet, that's a red flag. Second, don't overlook small amounts. I once spent weeks trying to reconcile my taxes because I was missing a $3 1099-DIV from a fractional share that got liquidated during a transfer. The IRS computers don't care if it's $3 or $3000 - they just want the numbers to match. Finally, if you have a tax preparer, give them a heads up about the account transfers BEFORE your appointment. They can often spot missing forms that you might not think of, and they may have contacts at the major brokerages who can expedite missing forms. My CPA has saved me from filing incomplete returns multiple times just by asking the right questions about my investment activity. The tools mentioned here like taxr.ai and Claimyr sound really helpful - I'm definitely going to check them out for next year's tax season!