Re: [MlMt] S/MIME Encryption

2017-02-17 Thread Benny Kjær Nielsen

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 
xyz@abc.com. 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 `xyz@abc.com`.

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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Re: [MlMt] S/MIME Encryption

2017-02-17 Thread Robert M. Münch
On 16 Feb 2017, at 11:29, Benny Kjær Nielsen wrote:

>> 1. I'm wondering how this works as I can't remember to send my S/MIME 
>> certificate. Is there something like a key-server for S/MIME as well?
>
> 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.

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. 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.


> 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?


>> 2. Answering the email with encryption & signing doesn't work. I get: 
>> "Failed to find valid certificate to encrypt for xyz@abc.com. 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?

> Have you checked that it's not expired or otherwise not trusted (view it in 
> Keychain Access)?

Yes, and I think it's correct.

> For debugging, you can send me the certificate off list and I can try 
> creating a message myself.

Done.

>> 3. When trying to send the email I need to enter the password for a signing 
>> certificate I own. This is the first keychain in the keychain app. But this 
>> certificate is not for encryption. Could it be that MM just access the first 
>> keychain and doesn't search through all of them?
>
> MailMate doesn't specify a specific keychain when doing certificate searches, 
> but I think the system library looks in the login keychain first.

I see the "Signing" and "Email Encryption" certificate there.

> When signing then MailMate only looks for certificates which can be used for 
> signing.

Which seems to work as I'm asked to enter the password for the USB token.

> 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.

-- 

Robert M. Münch, CEO
M: +41 79 65 11 49 6

Saphirion AG
smarter | better | faster

http://www.saphirion.com
http://www.nlpp.ch


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Re: [MlMt] S/MIME Encryption

2017-02-16 Thread Benny Kjær Nielsen

On 13 Feb 2017, at 11:27, Robert M. Münch wrote:

Hi, I received an encrypted S/MIME message which was successfully 
decrypted. At least that's what MM shows.


1. I'm wondering how this works as I can't remember to send my S/MIME 
certificate. Is there something like a key-server for S/MIME as well?


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


2. Answering the email with encryption & signing doesn't work. I get: 
"Failed to find valid certificate to encrypt for xyz@abc.com. 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. Have you 
checked that it's not expired or otherwise not trusted (view it in 
Keychain Access)?


For debugging, you can send me the certificate off list and I can try 
creating a message myself.


3. When trying to send the email I need to enter the password for a 
signing certificate I own. This is the first keychain in the keychain 
app. But this certificate is not for encryption. Could it be that MM 
just access the first keychain and doesn't search through all of them?


MailMate doesn't specify a specific keychain when doing certificate 
searches, but I think the system library looks in the login keychain 
first. When signing then MailMate only looks for certificates which can 
be used for signing. If you need to then you can force an explicit 
binding between an email address and a certificate using a [hidden 
preference](https://manual.mailmate-app.com/hidden_preferences#security).


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).


--
Benny
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