On 17 Feb 2017, at 10:16, Robert M. Münch wrote:

No, but when you sign a message then the recipient gains the ability to encrypt messages to you if they add your certificate to the keychain.

I think in S/MIME exist different types of certificates as I own one for signing but that can't be used for encryption. Not sure how this is handled.

This is not a problem when signing, but when encrypting then the message also needs to be encrypted for you (since otherwise you cannot view the message later on). MailMate cannot do this without a certificate available for doing encryption.

What is strange is this: I received an email where MM stated that it was successfully S/MIME decrypted. But I don't have any S/MIME encrypting certificate.

Your signing certificate must have been used to encrypt the message by the sender (I don't think this is technically a problem, but I don't think it is strictly correct behavior).

MailMate has also not been very good at checking whether or not certificates were marked for use for signing/encryption, but *I think* the latest releases do respect this.

So I'm wondering why MM displays this message. Further I don't have a clue how the one who send me the email would have gained access to my S/MIME certificates.

They get your certificate if you have sent a signed message to him/her.

I think this happens automatically in Apple Mail. In MailMate you have to explicitly add it to the keychain.

How do I add this to the keychain? Can I access the certificate anyhow?

Click on “Show Details” and then “Add to Keychain”.

2. Answering the email with encryption & signing doesn't work. I get: "Failed to find valid certificate to encrypt for [email protected]. The specified item could not be found in the keychain. Error code: -25300" (Note: This text is shown twice). But I can see the certificate for the recipient in one of my keychains.

The error code means that it couldn't find a valid certificate.

For whom? For me or the guy I'm going to send an email to?

For the one with the email address `[email protected]`.

S/MIME and OpenPGP users should update to the latest test release (r5346). I've made several changes which I would like to have tested including an important bug fix for S/MIME (which I would like to release soon).

Ok, will do.

Thanks!

--
Benny
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