Converted PFX SSL cert throwing SSLHandshakeException?

Question

I was given a PFX "wildcard" SSL certificate (I believe its a VeriSign cert) for *.ourdomain.example.org. I then used this answer to help me convert the PFX into a JKS keystore entry and add it to a JKS keystore. When I run keytool -list -keystore mykeys.jks I see:

Keystore type: JKS
Keystore provider: SUN

Your keystore contains 1 entry

<my key's long GUUID>, May 1, 2014, PrivateKeyEntry, 
Certificate fingerprint (SHA1): <cert's fingerprint>

So I know the converted PFX cert is in there. But at runtime, when JNDI is using SSL to establish a connection to my AD server (over LDAPS), I am seeing the following exception:

javax.net.ssl.SSLHandshakeException:
    sun.security.validator.ValidatorException: PKIX path building failed:
    sun.security.provider.certpath.SunCertPathBuilderException:
        unable to find valid certification path to requested target

I'm wondering if something got botched in the conversion from PFX to JKS. I'm pretty sure nothing else is wrong with the SSL cert, because I was using a self-signed cert before using this PFX and my browser was giving me the typical "I do not trust this certificate" warning. After I added the converted PFX and restarted my app, those warnings went away. Any ideas as to what could be going on here?

Answer 1

Firstly, in many cases, you don't need to convert from PKCS#12 (PFX) to JKS, many applications will let you set the keystore type to PKCS12 (instead of the default JKS), which will allow you to use your PFX file directly.

It looks like you're mixing up the usage of trust store and key store here (see this question).

Having a keystore with a certificate and its PrivateKeyEntry (here, coming from a PKCS#12 file) is normally used as a "keystore keystore" (as opposed to a keystore used as a truststore). This would normally be used for the certificate you present to your clients as a server, or the client certificate you use when connecting to a server that requests one.

Here, the "PKIX path building failed" exceptions means that your Java application doesn't trust the remote certificate it is connecting to. Presumably, your AD server has nothing to do with this JKS keystore. Rather, your server that uses your keystore is also a client to that AD server, and it cannot trust the AD server certificate.

You don't say how you've configured your application. Perhaps you've used your keystore for both the keystore and truststore settings (effectively preventing the use of the CA certificates bundled with the default JRE truststore), or perhaps your AD certificate is self-signed or not issued by a CA that is part of the default truststore. If the latter is the case, simply import the AD certificate (just the certificate, not the certificate and its private key) into the trust store (you can either do this into the JRE's cacert file or make a copy of it and use that using the javax.net.ssl.trustStore and related system properties).