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One question - who determines if I had earnings on the excess Roth contributions? Does the brokerage house determine this or do I need to figure out if that particular contribution generated any return?

Ultimately, you do. The brokerage may or may not assist you with the calculation, but as far as the IRS is concerned, you are responsible for the calculation.

If I was sitting on cash, then made the contribution, bought some stock, then sold some stock it seems murky as to whether or not that particular contribution generated a return, no?

I believe that same publication 590 talks about this calculation. You do not try to calculate the earnings on a specific contribution.

You take a look at the value of the account at the time of the contribution, and again at the time of withdrawal. The change in value is allocated proportionally between what was already in the account and your contribution. The specific investments are not relevant.

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