401(k) plans do not actively promote the ability to withdraw money from your 401(k) account before age 59?. In fact, some plans require you to take a loan from the plan before you can take a withdrawal. Most plans do, however, offer the ability to withdraw from your 401(k), which, under IRS regulations, must be for an \\\"immediate and heavy financial need.\\\" These so-called \\\"hardship withdrawals\\\" are allowed for the following reasons: Unreimbursed medical expense for yourself or a dependent Purchase of primary residence College tuition for yourself or a dependent To prevent eviction or foreclosure If you take a hardship withdrawal, the plan sponsor will set aside 20% as a prepayment of your federal taxes. An additional 10% premature withdrawal penalty may apply. There are some exceptions to the 10% premature withdrawal penalty, including: Disability (as defined by the IRS) A separation of service (after age 55 and prior to age 59?) If your withdrawal is distributed in the form of \\\"substantially equal payments\\\" made at least annually over your life expectancy or the joint life expectancy of you and your designated beneficiary Payments for certain unreimbursed medical expenses under the Internal Revenue Code Distributions to alternate payees required through Qualified Domestic Relations Orders (as might be issued in divorce proceedings) If you are considering taking a withdrawal, check with your plan sponsor or the IRS for more details. Source - http://www.quicken.com/cms/viewers/article/retirement/18339

1st you need to roll the 401(k) into a Rollover IRA then you can take a withdrawal to pay for health insurance. You will pay income taxes on the money but not the 10% penalty.

You should rollover or direct transfer your 401k to an IRA. You can start taking money out at age 59 1/2 (I believe).