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I am planning on transferring shares of my existing taxable mutual fund to open a Roth IRA in the same fund (TWCUX). I want to identify specific shares to limit my tax liability. I reinvest all dividends. My question is this:

Do I merely pick the most expensive shares purchased within the last 18 months or do I cost average ( picking shares held longer than 18 months) around the most recent share price as I have already paid taxes on those gains already?

Thanks in advance for the help!
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