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HelloThe Early Distribution penalty would not apply to a Roll Over. If you withdrew $100,000 on Oct 31 you would have 60 days to put $100,000 in another tax deferred account (or the same) to avoid tax and a penalty.
If you later withdrew $100,000 then you would not have the penalty but of course would owe tax on the distribution.
When you filed your return you would report the $200,000 distributed to you but $100,000 would be non taxable as long as you met the 60 day requirement.
I thought my response did go by your dates.
"take an IRA distribution on October 31,2015 for $100,000 , take another one for $100,000 on November 20,2015 and use that distribution to repay the first one"
You take out in Oct and need to put money, of same amount, back within 60 days.
As long as you put in the same amount taken out with in 60 days of that Oct date you have a rollover. It does not matter where you get the money from.
They could always challenge any thing but as long as your actions were consistent and you stay within the 60 days of the first you would be within the rules.
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