From what I understand the first "used" mission will be insured.

Insurers seem to be playing a bit loose with SpaceX:

>This insurance official said that given the market’s current softness, underwriters have overlooked the fact that they are not always sure what modifications have been made to the Falcon 9 they are insuring.

http://spacenews.com/spacex-to-brief-underwriters-on-the-roa...