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At Vanguard, can I transfer shares from regular investment account to a Roth IRA?
No, IRA contributions can only be made in the form of cash (rollovers and conversions are different). You'd have to sell the investments in your taxable account, incurring capital gains or losses, then transfer the proceeds to your IRA in cash. Note that the amount you can transfer is subject to the limits on how much one can contribute to the IRA each year. You could look into Vanguard Target Retirement funds, which have a lower $1,000 minimum investment, or Vanguard ETFs.