I don't really understand PGP/GPG, either. But what I can vaguely glean from what I read is that GPG has 2 ways of deciding whether to trust a key. One is based on signatures, and one is based on what I tell it (that's what accounts for the 5 and 6 ratings -- me just saying I trust this key). Perhaps the way MailMate interacts with GPG means that it uses only the web of trust/signature model and ignores this other thing (which may be "user trust," I'm not sure). I'll dig around and see if I can figure it out, and post if I can.

Best,
r


On 28 Sep 2017, at 1:41, Benny Kjær Nielsen wrote:

On 27 Sep 2017, at 22:00, Robert Goldman wrote:

Whenever I try to send a message with GPG encryption, I get an "OpenPGP encryption failed dialog box." The horrible error message (I know -- this is GPG's fault, not MailMate's!) looks like this:

The fact that I chose to just pass on the error messages to the user shows that I did not dare to try to “translate” them into something more comprehensible :)

But the trust level on my recipient's key is 5 and mine is 6. So why does this fail?

You need to sign the key, e.g., using the “GPG Keychain” application or `gpg2`. This is not always necessary though. OpenPGP is based on a “web of trust” and there are other ways that `gpg2` might determine that a key is valid. The details can be found in the “Using trust to validate keys” on [this page](https://www.gnupg.org/gph/en/manual/x334.html).

I don't claim to understand the details of “trust” and “validity” and I often find it confusing myself. Luckily (for me), all this really happens outside of MailMate. If you want to debug how MailMate uses `gpg2` then you can see how it's used by enabling the `MmDebugSecurity` hidden preference and launching MailMate from a Terminal window. You should be able to simply copy/paste the `gpg2` command and the arguments provided by MailMate if you want to do what MailMate does directly on the command line.

I hope this helps.

--
Benny


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