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Is it possible to transfer stock I already own into my Roth IRA without having to sell the stock?
No. A deposit to an IRA must be in cash. A conversion from traditional IRA to Roth can be "in kind" i.e. As a stock transfer. Last, any withdrawals can also be in stock or funds.  IRS Publication 590, so important, it's now in 2 sections Part A and Part B, addresses IRA issues such as this as well as most others.  By the way - now on page 7 - "Contributions, except for rollover contributions, must be in cash."