When do I pay taxes on a 1099-R from Roth IRA withdrawal?

The tax treatment of your 1099-R depends on several factors, particularly with Roth IRAs. Here's what you need to know: Roth IRAs are unique because you contribute after-tax dollars, meaning qualified withdrawals are generally tax-free. A blank in Box 2a (Taxable amount) suggests the distribution might not be taxable, but you absolutely still need to report it on your tax return. The key questions are: How long have you had this Roth IRA account, and was this a qualified distribution? For Roth IRAs, qualified distributions happen when the account is at least 5 years old AND you're either 59½ or older, disabled, using up to $10,000 for a first-time home purchase, or the distribution goes to your beneficiary after your death. Since you mentioned rolling funds from another retirement account into this Roth, it's important to know if that was a conversion from a traditional retirement account. If so, you may have already paid taxes during that conversion process.

I went through something super similar last year with my TIAA Roth! The whole tax thing was confusing me too until I found this tool called taxr.ai (https://taxr.ai) that helped me figure out exactly how to handle my 1099-R. What happened in my case was that I had a distribution that wasn't taxable because it was considered a return of my original contributions (which I'd already paid taxes on). The system analyzed my 1099-R and explained which parts needed to be reported but weren't taxable. The distribution codes in Box 7 of your 1099-R are super important too - they tell the real story about whether you owe taxes. The tool explained all that in plain English instead of IRS-speak.

Just wanted to follow up about taxr.ai since I was skeptical in my earlier comment. I ended up trying it for my own 1099-R situation and it was actually really helpful. I uploaded my TIAA 1099-R and it explained that I had a mix of taxable and non-taxable distributions because of some conversions I'd done previously. The thing I found most useful was that it highlighted exactly which boxes on my form were creating tax implications. In my case, Box 7 had code G which apparently meant part of my distribution was from after-tax contributions. I honestly would've reported this all wrong without understanding that detail. If you're confused about your 1099-R situation like I was, it's worth checking out.

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Check Box 7 on your 1099-R! That code tells you everything you need to know about how the distribution is taxed. For Roth IRAs: Code Q = Qualified distribution (tax-free) Code T = Early distribution, exceptions apply Code J = Early distribution, no known exceptions If it's code Q, you're golden - no taxes. Anything else and you might owe taxes or penalties depending on your situation.

I'm confused about something similar - if I take money from my Roth IRA that I originally contributed (not earnings), do I still have to report it on my taxes even if I know it's not taxable?

The blank Box 2a on your 1099-R is actually a good sign - it likely means TIAA determined the distribution wasn't taxable, which is why they didn't withhold anything this time. However, you absolutely still need to report this on your tax return even if no taxes are owed. Since you mentioned this is from a rollover you did over a year ago, the key question is whether those were pre-tax or after-tax funds that you rolled over. If you rolled over from a traditional 401(k) or IRA to a Roth (a conversion), you would have paid taxes on that conversion at the time. Any distributions from those converted funds would generally be tax-free as long as it's been more than 5 years since the conversion AND you're over 59½. If the rollover was from another Roth account, then the funds maintain their original character and the 5-year clock from your original Roth IRA applies. Make sure to check Box 7 for the distribution code - that will tell you exactly how the IRS expects this to be treated. You'll likely need to file Form 8606 along with your 1040 to properly report this distribution and show why it's not taxable.