Law Order
via Lavabit
Eventually, under government pressure, Lavabit founder Ladar Levison closed down his site and nuked the servers. Ostensibly, he did this rather than comply with government requests.
Following his many subsequent calls to unseal documents related to the FBI's case against him, we find out that Levison actually offered to comply - though not how they had in mind.
Initially, investigators wanted Levison to supply them with the means to wiretap select email users in order to get metadata - this was in July, so they were most likely shooting for Snowden's location data.
Levison decided to comply but wanted funding to provide the wiretap, but he wanted compliance funds to the tune of $3,500. Investigators apparently declined [see document below] because the proposal would not include real-time data and because they thought it was too much money.
Fed up, the FBI went back to court and got an order for SSH
In what TechCrunch called "an epic troll," Levison gave investigators his keys but printed them in 4-point font and filling 11 full pages.
"Each of the five encryption keys contains 512 individual characters - or a total of 2,560 characters," wrote prosecutors. "To make use of these keys, the FBI would have to manually input all 2560 characters, and one incorrect keystroke in this laborious process would render the FBI collection system incapable of collecting decrypted data."
The Bureau considered this submission "illegible" but laborious was probably a more accurate description.
It's impossible, though, to know if Levison actually "complied" with requests, or fed them an encryption key with one character altered - if so, it would have taken the FBI a million years to troubleshoot the missing or changed character.
Meanwhile, Levison's lawyer was furiously appealing the rulings.
Finally, rather than allow the government to seize his data and compel him to decrypt it, Levison shut down his site.
Here's the excerpt:
via U.S. Government