IRA Rollover of Stock

I can tell you a bit about the mechanics - which don't work correctly (Q2009 RPM R6).

Quicken intends to determine the tax impact of transfers of cash into and out of investment accounts by looking at the "Tax Attributes" for the account. [Click "Options > Set Tax Attributes" on the Account Attributes pane on the Overview tab of the account to see how your Tax Attributes are set.]

If Quicken was working correctly, I assume the steps to take would be: sell securities in IRA account; transfer cash to Roth IRA account; buy securities in Roth IRA account. [Alternatively, you might be able to use Remove Shares transactions in the IRA, a cash adjustment in the IRA for the value of the securities, a transfer of cash to the Roth IRA, then multiple Add Shares transactions in the Roth IRA account.]

But if you transfer cash out of a Quicken tax-deferred account into another investment account; Quicken doesn't treat the transfer according to the Tax Attributes setting. In order to get the correct tax treatment in Quicken, you need to transfer the cash to a non-investment account.

To overcome that problem, you could setup a dummy intermediate non-investment account; transfer the cash from the IRA to that intermediate account, then immediately transfer the funds out of the intermediate account and into the Roth IRA. The transfer out of the IRA will appear in the Tax Planner and the Tax Schedule report (assuming you've assigned the correct Tax Line Item to the transfer out in the Tax Attributes of the IRA account).

Even that transfer into the Roth IRA will not be treated correctly (though Quicken would have no way of knowing what to do in this case); Quicken will call the transfer into the Roth IRA a "contribution" ... but since it's a Roth IRA, I don't think this has much significance.

I don't use Turbo Tax, so I can't comment on the effects there.

[Ideally, Quicken would have some sort of rollover transaction ... as of Q2009, it doesn't.]