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I am very clueless when it comes to certificates/security and the like so please excuse my ignorance.

I purchased a certificate and it was sent to me. I generated the CSR using the java keytool. I managed to use OpenSSL to extract the private key from the keystore.

I am using a mail server called SmarterMail, and I wish to use the certificate for SMTP TLS.

Smartermail requires me to point to the certificates location, but it needs to know the private key (I assume)

I tried merging the crt and the private key into a .pfx file, but smartermail does not recognize that format.

So what I am asking is, is there a way I can merge the crt and the private key. install it. export it from windows certificate export wizard with "export private key" and have it as Base-64 encoded X.509 (.CER) That is the format SmarterMail wants.

Thank you so much.

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From the below link , smartermail needs you to provide the pfx [containing private key and public key protected by your password] and provide a base64 encoded copy of your certificate.

If you have the private key and certificate with you in separate files then you can use one of several tools[openssl etc] to make a pfx from the key and cert.

Steps to configure SSL on smartermail

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  • Thank you for your reply, that link is for an older version on SmarterMail and those menus don't exist anymore. I used this one , and even though it says "Export without private key" I found someone else who had my problem and his solution says export with private key.
    – Fuzz
    Jul 4, 2014 at 8:49
  • As i have mentioned in the answer , you are referring to the certificate export in base64 format since smartermail can read only b64 format. For this you should export without private key only as given in the steps in link.
    – Arun
    Jul 4, 2014 at 10:03
  • Thanks again, I did that but I get this exception in the smartermail logs : Exception negotiating TLS session: System.NotSupportedException: The server mode SSL must use a certificate with the associated private key. Do you think I need to add the private key to my keystore? (I am using the java keytool if that matters)
    – Fuzz
    Jul 4, 2014 at 11:16
  • I suggest you to provide the pfx with the as explained in the link i gave you . The menu structure would have change but i feel you can still find the option.
    – Arun
    Jul 7, 2014 at 14:18

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