Spring Boot / SSL and BadPaddingException

Are you working on getting SSL self signed certificates working with Spring Boot and getting a javax.crypto.BadPaddingException? Hopefully this post will save you some time.

I created this post to help remind myself and hopefully spare others the frustration of an issue that my co-worker and I ran into when setting up SSL on a project.

We developed a script that would generate a self signed p12 keystore for the application to use for local development and to test out our process before requesting the private key / certificates we needed from the client to secure the application we were developing.

#!/usr/bin/env sh
 
# passwords for the local generated certs
export KEY_STORE_PASSWORD=keyStorePassword
export KEY_PASSWORD=keyPassword
 
# Pick which OpenSSL to use - system default or one installed with Homebrew
export OPENSSL=openssl
#export OPENSSL=/usr/local/opt/openssl/bin/openssl
 
# Clean any previously-generated keys or certs
rm -rf ./generated
mkdir ./generated
 
# Generate Root CA Certificate
 
$OPENSSL genrsa -aes256 \
                -out ./generated/ca.key.pem -passout env:KEY_PASSWORD \
                4096
 
$OPENSSL req -config openssl.ca.cnf -batch \
             -new -x509 -days 3650 \
             -key ./generated/ca.key.pem -passin env:KEY_PASSWORD \
             -out ./generated/ca.cert.pem -passout env:KEY_PASSWORD
 
# Generate Server Certificate signed by Root CA
 
$OPENSSL genrsa -aes256 \
                -out ./generated/localhost.key.pem -passout env:KEY_PASSWORD \
                4096
 
$OPENSSL req -config openssl.server.cnf -extensions server_cert -batch \
             -new -days 3650 \
             -key ./generated/localhost.key.pem -passin env:KEY_PASSWORD \
             -out ./generated/localhost.cert.csr -passout env:KEY_PASSWORD
 
$OPENSSL x509 -extfile openssl.server.cnf -extensions server_cert \
              -req -sha512 -days 3650 \
              -in ./generated/localhost.cert.csr -passin env:KEY_PASSWORD \
              -CAkey ./generated/ca.key.pem -CA ./generated/ca.cert.pem -set_serial 1000 \
              -out ./generated/localhost.cert.pem
 
# Convert Server Key and Certificate to proper format for java trust store
 
$OPENSSL pkcs12 -export -name localhost -caname "Localhost CA" \
                -inkey ./generated/localhost.key.pem -passin env:KEY_PASSWORD \
                -in ./generated/localhost.cert.pem \
                -certfile ./generated/ca.cert.pem \
                -out ./generated/localhost.p12 -passout env:KEY_STORE_PASSWORD

Once we had created the keystore and verified the certs looked correct, we started up the application with the new keystore referenced in the application configuration.

server:
  port: 8443
  ssl:
    enabled: true
    key-store: ./certs/generated/localhost.p12
    key-store-password: keyStorePassword
    key-store-provider: SunJSSE
    key-store-type: PKCS12
    key-password: keyPassword
    key-alias: localhost

To our surprise we were greeted with the following error.

Caused by: javax.crypto.BadPaddingException: Given final block not properly padded. Such issues can arise if a bad key is used during decryption.
        at com.sun.crypto.provider.CipherCore.doFinal(CipherCore.java:991) ~[sunjce_provider.jar:1.8.0_171]
        at com.sun.crypto.provider.CipherCore.doFinal(CipherCore.java:847) ~[sunjce_provider.jar:1.8.0_171]
        at com.sun.crypto.provider.PKCS12PBECipherCore.implDoFinal(PKCS12PBECipherCore.java:399) ~[sunjce_provider.jar:1.8.0_171]
        at com.sun.crypto.provider.PKCS12PBECipherCore$PBEWithSHA1AndDESede.engineDoFinal(PKCS12PBECipherCore.java:431) ~[sunjce_provider.jar:1.8.0_171]
        at javax.crypto.Cipher.doFinal(Cipher.java:2164) ~[na:1.8.0_171]
        at sun.security.pkcs12.PKCS12KeyStore.engineGetKey(PKCS12KeyStore.java:371) ~[na:1.8.0_171]
        ... 34 common frames omitted

Ok, we must have done something wrong when generating the key, certificates, or keystore, right? After following a number of guides trying to recreate the keystore using different methods and a lot of googling what could be causing this error, we changed the key store password and key password to match on a whim, and presto the application started up correctly.

server:
  port: 8443
  ssl:
    enabled: true
    key-store: ./certs/generated/localhost.p12
    key-store-password: keyStorePassword
    key-store-provider: SunJSSE
    key-store-type: PKCS12
    key-password: keyStorePassword
    key-alias: localhost

It turns out that the `passout` variable of the `OPENSSL pkcs12` command changes both the key store password and the key password to the supplied value. This was not readily apparent from the man (linux manual) pages we were examining.

OPENSSL pkcs12 -export -name localhost -caname "Localhost CA" \
                -inkey ./generated/localhost.key.pem -passin env:KEY_PASSWORD \
                -in ./generated/localhost.cert.pem \
                -certfile ./generated/ca.cert.pem \
                -out ./generated/localhost.p12 -passout env:KEY_STORE_PASSWORD

In summary, when using ‘openssl pksc12 -export’, the value supplied to ‘-passout’ will need to be provided to Spring Boot for both the ‘key-store-password’ and ‘key-password’ properties.

I created an example project that demonstrates this which can be found at github.

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