Roth IRA early withdrawal - vanguard 1099-R coding

[hornet99]

I opened a Roth-IRA back in 1998 with Scottrade and transferred it to Vanguard in 2008, where I continued to contribute annually until 2017. I began tIRA conversions into it in 2021 (paying associated income taxes) in anticipation of early withdrawals before I turn 59 1/2 (currently 53). My goal is to avoid all taxes and penalties.

If I understand corn18's withdrawal table (snippet below), I can withdrawal all of my contributions tax and penalty free right now if I want.

Question:

Vanguard has been tracking my contributions since 2008 and therefore know my contributions since that time. What they don't know is my Scottrade contributions. Unfortunately Scottrade no longer has those records and (of course) I didn't save my 5498s from back then. I did record my contributions in a spreadsheet. With this in mind, how does Vanguard correctly code my 1099-R such that it doesn't get characterized as early-distribution unqualified, and therefore subject to penalty and tax.

Thanks in advance,
Hornet








Corn18 ORDER OF DISTRIBUTIONS
Regular contributions
Taxable portion of first conversion
Nontaxable portion of first conversion
Each subsequent conversion, in order, with the taxable portion coming out first for each conversion
Earnings (any increase in value occurring inside the Roth IRA)

TAXES AND PENALTIES

UNDER AGE 59.5*
FIVE YEAR CONVERSION HOLDING PERIOD NOT MET*
Contributions: Tax-No; Penalty-No*
Conversions: Tax-No; Penalty-Yes (Taxable Portion)*
Conversions: Tax-No ;Penalty-No (Nontaxable Portion)*
Earnings: Tax-Yes; Penalty-Yes*

UNDER AGE 59.5*
FIVE YEAR CONVERSION HOLDING PERIOD MET*
Contributions: Tax-No; Penalty-No*
Conversions: Tax-No; Penalty-No (Taxable Portion)*
Conversions: Tax-No; Penalty-No (Nontaxable Portion)*
Earnings: Tax-Yes; Penalty-Yes*
I have a questions regarding Vanguard:

 

[cathy63]

Vanguard doesn't need to know your contributions history. They should issue a 1099-R with a J in box 7, indicating an early distribution from a Roth IRA.

You will need to fill out form 8606 Part III when you do your taxes. You will enter the withdrawal amount from box 1 of the 1099-R and the amount of your contributions that you kept track of. The form will tell you to subtract the latter from the former, and as long as it comes to zero or less, none of your withdrawal will be taxable.

The IRS will normally just believe you when you tell them on form 8606 how much you contributed to the account over time, but they also should have all your old 5498s that would also allow them to figure it if they wanted to.