Form asks for first year of designated Roth contribution. I do not remember and paper trail was destroyed. What year do I enter when I don't know?

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Check record on-line with account custodian(s). Lacking that, won't matter much if you can (eventually) prove first time was at least five years ago ...

The issuer of the 1099-R enters that on the form if this is a 1099-R for a designated Roth and the box 7 code indicated a designated Roth (code B or H). Enter what the form you received has or blank of no entry on your 1099-R.

**Disclaimer: This post is for discussion purposes only and is NOT tax advice. The author takes no responsibility for the accuracy of any information in this post.**