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But what are the mechanics of doing this? Do I contact the brokerage and have them make the starting move?

Are your Traditional accounts IRAs? And are your Roth accounts IRAs? As Wradical indicated, moving your money into IRAs from employer plans will probably make conversions a little easier.

And then answer to the mechanics is - it depends on your administrator/custodian. Many of them make it pretty easy to do on their website, especially if you are converting between accounts at the same brokerage, without having to contact the brokerage at all. If you want to do a conversion between brokerages, you may have better luck starting with the brokerage that has the Roth, and asking them to pull from the brokerage that has the Traditional.

Do I designate a dollar amount that should be converted -- or can I designate some specific investments that are to be converted?

You can do either. The mechanics of doing each depend on your administrator/custodian, but it is possible to convert either a dollar amount or a specific investment.
AJ
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