... for me with Java 1.8.0 332 (various OpenJDK builds) on TC 9.0.63 and 10.0.21, platform various Linuxes and also Solaris Sparc. It does not fail for Java 11 and also not for Oracle Java 1.8.0 331.

Testsuite: org.apache.tomcat.util.net.jsse.TestPEMFile
Tests run: 5, Failures: 0, Errors: 1, Skipped: 0, Time elapsed: 0.947 sec

Testcase: testKeyEncryptedPkcs1DesEde3Cbc took 0.59 sec
Testcase: testKeyEncryptedPkcs8 took 0.196 sec
        Caused an ERROR
Cannot retrieve the PKCS8EncodedKeySpec
java.security.spec.InvalidKeySpecException: Cannot retrieve the PKCS8EncodedKeySpec at javax.crypto.EncryptedPrivateKeyInfo.getKeySpec(EncryptedPrivateKeyInfo.java:258) at org.apache.tomcat.util.net.jsse.PEMFile$Part.toPrivateKey(PEMFile.java:212)
        at org.apache.tomcat.util.net.jsse.PEMFile.<init>(PEMFile.java:143)
        at org.apache.tomcat.util.net.jsse.PEMFile.<init>(PEMFile.java:98)
at org.apache.tomcat.util.net.jsse.TestPEMFile.testKey(TestPEMFile.java:74) at org.apache.tomcat.util.net.jsse.TestPEMFile.testKeyEncrypted(TestPEMFile.java:69) at org.apache.tomcat.util.net.jsse.TestPEMFile.testKeyEncryptedPkcs8(TestPEMFile.java:64) 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.unpad(CipherCore.java:975)
at com.sun.crypto.provider.CipherCore.fillOutputBuffer(CipherCore.java:1056)
        at com.sun.crypto.provider.CipherCore.doFinal(CipherCore.java:853)
at com.sun.crypto.provider.PBES2Core.engineDoFinal(PBES2Core.java:323)
        at javax.crypto.Cipher.doFinal(Cipher.java:2168)
at javax.crypto.EncryptedPrivateKeyInfo.getKeySpec(EncryptedPrivateKeyInfo.java:253)

Testcase: testKeyPkcs1 took 0.004 sec
Testcase: testKeyEncryptedPkcs1Aes256 took 0.035 sec
Testcase: testKeyEncryptedPkcs1DesCbc took 0.023 sec

Best regards,

Rainer

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