A good way to regain and build trust with users would have been to acknowledge his previous mistakes. Then at least you could say "he's been around the block, done it wrong and learned how to do it right". Instead, he writes:

"In August 2013, I was forced to make a difficult decision: violate the rights of the American people and my global customers or shut down. I chose Freedom."

That isn't what happened. He chose to build and sell a supposedly secure email service that was fundamentally vulnerable to government intrusion. He then decided to play chicken with the USG over a warrant no different than ones he'd complied with previously. The completely pointless escalation forced him to compromise all of his users, something the government had not been asking for. He then shut the service down.

There are a lot of ways to describe this but 'I chose Freedom' without any acknowledgment of his previous mis-steps is both misleading and shameless. I wouldn't buy supposedly secure services from him.

If Edward Snowden started a mail service, I'd probably trust it more. If you want to talk about "going to the mat" for people, I think Snowden has made the bigger sacrifice.

Moxie and Whisper Systems probably would get my nod too. Perhaps even DJB or Bruce Schnier.

He didn't go to the mat for his users. He built a service that he knew was vulnerable to standard legal process (or if he didn't, he was amazingly incompetent) but sold it as if it were safe from the government, duping even Edward Snowden. The government, naturally, engaged in standard legal process, and found that he possessed a key that would give the government access to everything they needed, and that he was capable of turning it over. So he was ordered to turn it over, which should have surprised no one.

He did surrender the key, although by printing out the key in 4-point font (unclear if he was buying time, or just thought contempt charges sounded fun). After the government pressed him harder, he shut down the service days later. He didn't disclose that he had surrendered the key; the public found out when the court documents, including the key itself, were unsealed.

If something can't be done securely, don't tell your users that it can be done securely. If you know you can't win, there's honor in refusing to lose without a fight. But there's no honor in first promising people that you'll win, and there's quite a bit of dishonor in asking people to pay you to win.

Lavabit v1 should never have been built. Many people were technically qualified to build something like it it (it's email, which constrains the design significantly), had the resources, and chose not to. The fact that Levison built it, and that he hasn't apologized for building it, demonstrates that he's untrustworthy. This is not to say that he's a bad person; everyone makes mistakes, and I wouldn't trust myself to build a secure email service singlehandedly, because I know what mistakes I've made and what sort of personality flaws I have. It's just a statement that the required level of trust is extremely high, and Levison hasn't demonstrated it.

Lavabit v2's "Trustful" mode has all of the same flaws as Lavabit v1. He writes about his "free and open source server" and asks how you feel about "trusting our servers," when that was never the problem. If you can magically make sure that the government doesn't have access to your system, a standard unencrypted email server will do just fine. If you can't, they'll issue the exact same legal order to Lavabit v2 that they did to v1, and it'll be just as effective.

Phil Zimmermann

He went to prison over pgp.

But then the mail service he was involved in (silent circle mail) shut down at the same time as lavabit.

Vincent Canfield