Hi there

I have some trouble using ssl in Apples Mail.
I have two certificates, one for private (j...@me.com) and one for business 
(j...@acme.com).
Both are valid certificates from Verisign.

With both certificates I can sign and encrypt (ok, encrypt not really depends 
on my cert), but I can decrypt only with the company cert.
For whatever reason Mail alway reports that it cannot decrypt the email for my 
private account.

So I exported the email as plain file (.eml extension). I also exported the 
corresponding certificate plus the key as .cert files and converted them using 
openssl (e.g. openssl x509 -inform der -in key2.cer -out key2.pem).

If I now use openssl to decrypt, I get the following message:

---cut---
Dilbert:test user$ openssl smime -decrypt -recip cert.pem -inkey key2.pem -in 
smime.p7m 
Enter pass phrase for key2.pem:
Error reading S/MIME message
3040:error:2107A087:PKCS7 routines:SMIME_read_PKCS7:no content 
type:/SourceCache/OpenSSL098/OpenSSL098-30/src/crypto/pkcs7/pk7_mime.c:296:
Dilbert:test adieball$ openssl smime -decrypt -recip cert.pem -inkey key2.pem 
-in testmail.eml 
Enter pass phrase for key2.pem:
Error decrypting PKCS#7 structure
3111:error:21070073:PKCS7 routines:PKCS7_dataDecode:no recipient matches 
certificate:/SourceCache/OpenSSL098/OpenSSL098-30/src/crypto/pkcs7/pk7_doit.c:450:
3111:error:21072077:PKCS7 routines:PKCS7_decrypt:decrypt 
error:/SourceCache/OpenSSL098/OpenSSL098-30/src/crypto/pkcs7/pk7_smime.c:470:
Dilbert:test user$
---cut---

I double-checked the mail for recipient Name and email and both are correct 
(case sensitivity checked). 

Beginning of key2.pem:

---cut---
Bag Attributes
    friendlyName: Schl<FC>ssel von digitalid.verisign.com
    localKeyID: 18 CA 83 04 84 DD 09 4B F9 E0 4B DC B0 DF 19 7B D1 A5 13 0B 
Key Attributes: <No Attributes>
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: DES-EDE3-CBC,F011FC14BD2F6ECF

sG3trM0OgPDbf8MqzlKl1y5tEz4jqq5N1V2PfJjf8BY8DlxEcMZEcbe8aKcp6DxM
wuWzMY+QE60d64m3waX1WmHj9Iw9BaDz+SGBwSO1CpDkkPG/Ug0ohdmRvwKuDLNV
[...]


Beginning of cert2.pem:

---cut---
Bag Attributes
    friendlyName: John Doe
    localKeyID: 18 xx 83 xx 84 xx xx xx [...} 
subject=/O=VeriSign, Inc./OU=VeriSign Trust 
Network/OU=www.verisign.com/repository/RPA Incorp. by 
Ref.,LIAB.LTD(c)98/OU=Persona Not Validated/OU=Digital ID Class 1 - Netscape 
Full Service/CN=John Doe/emailaddress=j...@me.com
issuer=/C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=Terms of use at 
https://www.verisign.com/rpa (c)05/OU=Persona Not Validated/CN=VeriSign Class 1 
Individual Subscriber CA - G2
-----BEGIN CERTIFICATE-----
MIIFXjCCBEagAwIBAgIQKHvbtcfTy5QhIodqOcjMXDANBgkqhkiG9w0BAQUFADCB
3TELMAkGA1UEBhMCVVMxFzAVBgNVBAoTDlZlcmlTaWduLCBJbmMuMR8wHQYDVQQL

[...}

(changed Name, Email and Key ID)

OpenSSL> version
OpenSSL 0.9.8l 5 Nov 2009
OpenSSL> 


Any help in guiding me to the right direction is appreciated.


Thanks a lot in advance

Andre


Attachment: smime.p7s
Description: S/MIME cryptographic signature

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