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Do you have to leave/retire from a company in order to be able to roll your 401K into an IRA? Or, can I roll my 401K without leaving my current employer?

You have to leave.

how long ?
could i work something out with my company that i quit. Quickly roll my 401(k) and then get my job back the next week (month?) and start a new 401(k) ?

I certainly can't think of a reason that would be illegal-- MSFT fires and hires it's "temp" workers periodically to ensure they remain temps. Of course, you'd lose your vacation, seniority, time toward vesting etc. so it probably wouldn't be a great deal for you.
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