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You are not required to pay the early withdrawal penalty at all. "Separation from service" means you left the job, whether by retirement, quitting, fired or laid off. The distribution (withdrawal) in 2016, from your previous employer's 401k, does qualify for the separation from service exception, to the early (before age 59-1/2) withdrawal penalty because you were 55 or over when you separated. There is no time limit for the withdrawal.
Had you rolled over the 401k to an IRA, any subsequent distribution from the IRA would not qualify (but might qualify for the home buyer exception). Home buying is not a penalty exception to a 401k distribution (only IRAs).
You are not required to pay the early withdrawal penalty at all. "Separation from service" means you left the job, whether by retirement, quitting, fired or laid off. The distribution (withdrawal) in 2016, from your previous employer's 401k, does qualify for the separation from service exception, to the early (before age 59-1/2) withdrawal penalty because you were 55 or over when you separated. There is no time limit for the withdrawal.
Had you rolled over the 401k to an IRA, any subsequent distribution from the IRA would not qualify (but might qualify for the home buyer exception). Home buying is not a penalty exception to a 401k distribution (only IRAs).
A clarification question. Turn 55 in 2018 & separate from employer in June 2018. Would a 401K distribution in March 2018 still be exempt from the 10% penalty? ..or do you need to distribute after the separation in June to qualify for the exemption?
No, a distribution prior to separation from service does not qualify for the age-55 exception.
clarifying question - if I retire from company after age 55, meaning no W2, but continue doing some work for the company as a consultant, meaning 1099, does that still meet rule of 55 definition of "separate from service"?
The answer likely depends on the amount of service provided as an independent contractor. I'm not sure of the threshold, but if the amount of service provided as an independent contractor is a significant fraction of the amount provided as an employee, the IRS can consider you to be still employed with the company. However, the IRS is probably not going to question a code-2 Form 1099-R provided by the plan.
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