See my comment here[1]. While I'm not normally a government apologist, from the unsealed court documents, it appears that they did everything by the book here. The original order was for metadata related to a single, specific named account. There were several follow up orders and court proceedings before the request was broadened to turn over the SSL keys.
I'd claim that not producing evidence in response to a lawful subpoena and court order is proof that he's guilty of contempt of court[2].
[2] There are lawful ways to resist such an orders - you file a motion to oppose in the case. While I don't have access to PACER to confirm that no such motion was filed, the judge's orders have no mention of such a motion in the established facts.
I'd claim that not producing evidence in response to a lawful subpoena and court order is proof that he's guilty of contempt of court[2].
[1] https://news.ycombinator.com/item?id=6519732
[2] There are lawful ways to resist such an orders - you file a motion to oppose in the case. While I don't have access to PACER to confirm that no such motion was filed, the judge's orders have no mention of such a motion in the established facts.