Roth IRA: Does it not generate a 1099 form at all?

Thanks for the explanation! Does this mean if I've made both Roth and Traditional IRA contributions, I'd get a 1099 form for the Traditional but not for the Roth? Also, what happens if I made a contribution to my Roth IRA but then realized I wasn't eligible because I made too much money this year?

Yes, you would typically receive a Form 5498 showing your Traditional IRA contributions and a 1099-R if you took any distributions from the Traditional IRA, but you wouldn't receive any tax forms for your Roth IRA unless you took distributions. If you contributed to a Roth IRA but exceeded the income limits, you've made what's called an "excess contribution." You have a few options: remove the excess contribution (plus any earnings on it) before your tax filing deadline, apply it to next year's contribution if you'll be eligible then, or pay a 6% excise tax on the excess amount for each year it remains in your account. Your provider would issue forms if you remove the excess contribution.

How does that work exactly? Can it analyze statements from different brokerages or just certain ones? I've got accounts scattered across Vanguard, Fidelity and an old 401k from a previous employer.

That sounds useful but idk if I want to upload my financial documents to some random website. How secure is it? They're not selling our data or anything sketchy like that right?

It works with pretty much any brokerage statements - I've used it with both Vanguard and Schwab without issues. You just upload your documents and it extracts the relevant info automatically. The analysis shows exactly which forms to expect and why. They use bank-level encryption for all uploads and don't sell user data. Everything is processed securely and they're actually more private than most tax services since they don't require you to create an account with personal info if you don't want to. I was skeptical at first too but their privacy policy is pretty straightforward.

Wait, how does this actually work? The IRS phone system is notorious for disconnecting people after waiting for hours. How does this service actually get you through?

Sounds like BS honestly. Nobody can magically get through the IRS phone system. They probably just keep you on hold the same as if you called yourself. What makes them any different than me dialing the number myself?

The service basically navigates the IRS phone tree for you and waits in the queue until an agent is available. Then it calls you and connects you directly to the IRS agent. No more listening to hold music for hours or getting disconnected after waiting. They use technology that keeps your place in line no matter what, even if the call would normally drop. They've figured out how to navigate the system efficiently based on call volumes and timing. It's completely different than calling yourself because they're using a system specifically designed to maintain connection with the IRS queue without you having to stay on the phone the whole time.

So do I need to keep the Form 5498 for my records even though I don't file it? And what's the point of sending it if we don't need to report Roth contributions on our tax return?

Yes, you should definitely keep the Form 5498 with your tax records. While you don't file it with your return, it's important documentation that proves you made contributions to your Roth IRA. This can be valuable if you're ever audited or need to calculate the basis in your Roth IRA for early withdrawals. The IRS receives this form to track contribution limits and ensure compliance. It helps them verify you're not exceeding annual contribution limits across all your IRA accounts. It's also useful for you to confirm your financial institution correctly recorded your contributions.

They're probably sending you account statements or Forms 5498, not 1099s. The 5498 just confirms your contributions but isn't needed for filing. Check the actual form number at the top - if it says 5498, that's different from a 1099-R (which you'd only get if you took money out).

@Jasmine is right - you're likely receiving Form 5498 which reports your annual contributions, not a 1099 form. The 5498 arrives around May (after tax season) and is purely informational - you don't need to file it with your taxes. It's just documentation that you contributed to your Roth IRA during the tax year. The only time you'd get a 1099-R from your Roth IRA is if you actually withdrew money from the account, which would need to be reported on your tax return.

This is really helpful to hear from someone with professional experience! I'm glad to know that the simplicity is actually by design. One quick follow-up question - if I ever do decide to do a backdoor Roth conversion in the future (since my income might go up), would that generate additional forms beyond the 1099-R you mentioned? I want to make sure I understand the full picture before I potentially get into that territory.