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I am just staring out in investing and I have a Roth IRA that I invest $50 into every month into a mutual fund. I have $10,000 in different stocks in just a plain account with my broker. I want to roll these stocks into my roth so when I sell them after I am 60 I won't have to pay the significant amount of capitol gains that will accumulate in the next 40+ years, ( I am only 20). I am wondering if and how I should get these stocks into my Roth.

Nice try, but you can't do that. Contributions to an IRA (Roth or otherwise) are limited to cash only. It is possible to transfer assets (like stocks) into an IRA, but only when they are coming from another retirement plan. So forget the idea of moving stocks from a plain brokerage account into your IRA - it ain't gonna happen! You're stuck with those capital gains, but that's not such a bad thing.

Also I wanted to know if the dividend re-investment that I do on these stocks will count toward my total annual roth contribution.

Earnings (dividends, capital gains, whatever) inside an IRA do not count toward the annual contribution. What counts is new money going into the account (in the form of cash!) from outside.

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