Question

I’m trying to configure a Tomcat server with SSL. I’ve generated a keypair thus:

$ keytool -genkeypair -alias tomcat -keyalg RSA -keystore keys

Next I generate a certificate signing request:

$ keytool -certreq -keyalg RSA -alias tomcat -keystore keys -file tomcat.csr

Then I copy-paste the contents of tomcat.csr into a form on Thawte’s website, asking for a trial SSL certificate. In return I get two certificates delimited with -----BEGIN ... -----END, that I save under tomcat.crt and thawte.crt. (Thawte calls the second certificate a ‘Thawte Test CA Root’ certificate).

When I try to import either of them it fails:

$ keytool -importcert -alias tomcat -file tomcat.crt -keystore keys
Enter keystore password:
keytool error: java.lang.Exception: Failed to establish chain from reply

$ keytool -importcert -alias thawte -file thawtetest.crt -keystore keys
Enter keystore password:
keytool error: java.lang.Exception: Input not an X.509 certificate

Adding the -trustcacerts option to either of these commands doesn’t change anything either.

Any idea what I am doing wrong here?

Answer 1

I finally understood what was going on here. It turns out that the replies that I got from Thawte are formatted as PKCS#7, whereas keytool expects certificated in the X.509 format.

openssl can be used to convert certificates from one format to another:

$ openssl pkcs7 -in thawtetest.crt -print_certs |
  openssl x509 > thawtetest.x509

Now you can import thawtetest.x509 with keytool, and tomcat.crt right behind it.