When may I withdraw my Roth IRA earnings income tax-free?

The recharacterization of IRA contributions is a change of the annual contribution made to a Traditional or Roth IRA into the other IRA type. This includes the designation of a contribution plus earnings from one IRA type into the other IRA type.

Recharacterzied contributions do not include Roth Conversions or Rollovers…

You can withdraw funds from your IRA at any time but in general, withdrawing funds from your IRA prior to age 59 ½ means you'll have to pay a 10% early withdrawal penalty. You may avoid the penalty if you're withdrawing because of:

• First time home purchase (USD 10,000 lifetime limit)…

An "early" withdrawal is generally one taken before age 59½ in a traditional IRA or within the first five years of a Roth IRA. In addition to the amount added to your income, the IRS may assess an additional 10% penalty. You should consult with your tax advisor regarding the tax consequences…

Yes, an employee can withdraw from the SIMPLE IRA whenever they wish. They will be subject to tax requirements.

SIMPLE IRA withdrawals are typically subject to income tax on any amount withdrawn.  Early withdrawals, which are those made prior to the account holder reaching the age of 59 ½, may be subject to an additional tax of 10% or 25%…