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I have qualified stock options for the company I work for, and want to have them paid for out of my Roth IRA. Can I do this?

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No, you cannot.

ISO are given to you in your capacity as an employee (that's why it is "qualified"), while your IRA is not an employee. You cannot transfer property to the IRA, so you cannot transfer them to the IRA once you paid for them as well.

This is different from non-qualified stock options (discussed in this question), which I believe technically can be granted to IRA. But as Joe suggests in his answer there - there may be self-dealing issues and you better talk to a licensed tax adviser (EA/CPA licensed in your State) if this is something you're considering to do.

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