Thanks for the reply. I'll be 59.5 at the end of this year.
Long story, but I am currently receiving some Roth 401K funds as part of my monthly distribution now before I am 59.5. Last year they sent me 2 1099's, one from pre-tax showing it was all taxable and one for my Roth with only the earnings showing taxable. The question I have is this: If I transfer my Roth funds from 401K to my brand new IRA and then turnaround and attempt to withdrawal all of it in 2026 (contributions and earnings). Will they send me the earnings without knowing I meet the 5 year rule? Maybe the 1099 they send will reflect taxes on the earnings and that will get sorted when I do my taxes for the year?
Again, I don't know the specific rules on Roth 401(k)s.
But the way taxes generally work, the custodian will send you a 1099 with the distribution, the taxable amount, whether the taxable amount was not determined, taxes withheld, and a distribution code.
You'll then report that 1099 on your tax return, ideally correctly, knowing your whole tax situation.
The custodian doesn't need to know about the 5 year rule or your other Roths or anything else. They'll be able to complete the 1099 with what they know. That, plus what you know, is what results in your tax return being prepared correctly. At the end of the day, it's the taxpayer who's responsible for their tax return, not the custodian. If, for example, the custodian doesn't know that you met the 5 year rule, but you do, then there will be a way to handle that on your return.
To answer your specific questions in order:
1. They'll send you whatever distribution you request. It's up to you to understand the tax consequences of your requests.
2a. I don't know what you mean by "taxes on the earnings". I think normally Roth distributions don't have any taxes withheld. That being said, the custodian may withhold federal and/or state income taxes if you ask them to. But the actual taxability of the distribution will be determined by your tax return, not by what they do.
2b. Yes, it should get sorted on your tax return.