SSLPoke

Test establishment of a TLS connection to a host with Java.

This version has been enhanced to print all known system and security properties relevant to TLS and HTTPS.

Usage

Positive test:

java -jar sslpoke.jar www.github.com 443

You should get this:

connecting to www.github.com:443 with the following system and security properties:
java.version: System: 1.8.0_251
java.vendor: System: Oracle Corporation
policy.allowSystemProperty: Security: true
java.security.policy:
CertPathValidator.PKIX:
cert.provider.x509v1:
java.protocol.handler.pkgs:
security.provider.1: Security: sun.security.provider.Sun
ssl.ServerSocketFactory.provider:
ssl.SocketFactory.provider:
jdk.tls.client.protocols:
jdk.tls.disabledAlgorithms: Security: SSLv3, RC4, DES, MD5withRSA, DH keySize < 1024, EC keySize < 224, 3DES_EDE_CBC, anon, NULL
jdk.tls.legacyAlgorithms: Security: K_NULL, C_NULL, M_NULL, DH_anon, ECDH_anon, RC4_128, RC4_40, DES_CBC, DES40_CBC, 3DES_EDE_CBC
jdk.tls.ephemeralDHKeySize:
jsse.enableSNIExtension:
https.cipherSuites:
https.protocols:
sun.security.ssl.allowUnsafeRenegotiation:
sun.security.ssl.allowLegacyHelloMessages:
keystore.type: Security: jks
keystore.type.compat: Security: true
javax.net.ssl.trustStore:
javax.net.ssl.trustStorePassword:
javax.net.ssl.trustStoreType:
javax.net.ssl.keyStore:
javax.net.ssl.keyStorePassword:
javax.net.ssl.keyStoreType:
CertPathValidator.PKIX:
jdk.certpath.disabledAlgorithms: Security: MD2, MD5, SHA1 jdkCA & usage TLSServer, RSA keySize < 1024, DSA keySize < 1024, EC keySize < 224
com.sun.net.ssl.checkRevocation:
com.sun.security.enableCRLDP:
com.sun.security.crl.timeout:
sun.security.certpath.ldap.cache.lifetime:
com.sun.security.enableAIAcaIssuers:
ocsp.enable:
ocsp.responderURL:
ocsp.responderCertSubjectName:
ocsp.responderCertIssuerName:
ocsp.responderCertSerialNumber:
http.nonProxyHosts:
https.protocols:
https.proxyHost:
https.proxyPort:
java.security.debug:
javax.net.debug:

Successfully connected.
Protocol: TLSv1.2
Cipher suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256

Negative tests (courtesy of badssl.com):

java -jar sslpoke.jar expired.badssl.com 443
java -jar sslpoke.jar wrong.host.badssl.com 443
java -jar sslpoke.jar self-signed.badssl.com 443
java -jar sslpoke.jar untrusted-root.badssl.com 443
java -jar sslpoke.jar revoked.badssl.com 443
java -jar sslpoke.jar cbc.badssl.com 443
java -jar sslpoke.jar rc4-md5.badssl.com 443
java -jar sslpoke.jar rc4.badssl.com 443
java -jar sslpoke.jar 3des.badssl.com 443
java -jar sslpoke.jar null.badssl.com 443
java -jar sslpoke.jar tls-v1-0.badssl.com 1010
java -jar sslpoke.jar tls-v1-1.badssl.com 1011
java -jar sslpoke.jar tls-v1-2.badssl.com 1012

Which should get you an error like this:

[...]
Connection failed.
javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: validity check failed
        at sun.security.ssl.Alerts.getSSLException(Unknown Source)
        at sun.security.ssl.SSLSocketImpl.fatal(Unknown Source)
        at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
        at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
        at sun.security.ssl.ClientHandshaker.serverCertificate(Unknown Source)
        at sun.security.ssl.ClientHandshaker.processMessage(Unknown Source)
        at sun.security.ssl.Handshaker.processLoop(Unknown Source)
        at sun.security.ssl.Handshaker.process_record(Unknown Source)
        at sun.security.ssl.SSLSocketImpl.readRecord(Unknown Source)
        at sun.security.ssl.SSLSocketImpl.performInitialHandshake(Unknown Source)
        at sun.security.ssl.SSLSocketImpl.writeRecord(Unknown Source)
        at sun.security.ssl.AppOutputStream.write(Unknown Source)
        at sun.security.ssl.AppOutputStream.write(Unknown Source)
        at SSLPoke.connect(SSLPoke.java:51)
        at SSLPoke.main(SSLPoke.java:84)
Caused by: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: validity check failed
        at sun.security.validator.PKIXValidator.doValidate(Unknown Source)
        at sun.security.validator.PKIXValidator.engineValidate(Unknown Source)
        at sun.security.validator.Validator.validate(Unknown Source)
        at sun.security.ssl.X509TrustManagerImpl.validate(Unknown Source)
        at sun.security.ssl.X509TrustManagerImpl.checkTrusted(Unknown Source)
        at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(Unknown Source)
        ... 11 more
Caused by: java.security.cert.CertPathValidatorException: validity check failed
        at sun.security.provider.certpath.PKIXMasterCertPathValidator.validate(Unknown Source)
        at sun.security.provider.certpath.PKIXCertPathValidator.validate(Unknown Source)
        at sun.security.provider.certpath.PKIXCertPathValidator.validate(Unknown Source)
        at sun.security.provider.certpath.PKIXCertPathValidator.engineValidate(Unknown Source)
        at java.security.cert.CertPathValidator.validate(Unknown Source)
        ... 17 more
Caused by: java.security.cert.CertificateExpiredException: NotAfter: Mon Apr 13 01:59:59 CEST 2015
        at sun.security.x509.CertificateValidity.valid(Unknown Source)
        at sun.security.x509.X509CertImpl.checkValidity(Unknown Source)
        at sun.security.provider.certpath.BasicChecker.verifyValidity(Unknown Source)
        at sun.security.provider.certpath.BasicChecker.check(Unknown Source)
        ... 22 more

Java Properties

The properties that influence the network, TLS protocol, certificate verification and debugging behavior of a JVM are described in:

Java Secure Socket Extension (JSSE) Reference Guide (Java 8, Java 11)
Java PKI Programmer's Guide
Networking Properties

So far, I've come across the following parameters that seem relevant:

Policy
- policy.allowSystemProperty
- java.security.policy
Implementation
- cert.provider.x509v1
- java.protocol.handler.pkgs
- security.provider.1
- ssl.ServerSocketFactory.provider
- ssl.SocketFactory.provider
Protocol
- jdk.tls.client.protocols
- jdk.tls.disabledAlgorithms
- jdk.tls.legacyAlgorithms
- jdk.tls.ephemeralDHKeySize
- jsse.enableSNIExtension
- https.cipherSuites
- https.protocols
- sun.security.ssl.allowUnsafeRenegotiation
- sun.security.ssl.allowLegacyHelloMessages
Stores
- keystore.type (https://docs.oracle.com/javase/8/docs/api/java/security/KeyStore.html)
- keystore.type.compat (https://bugs.java.com/bugdatabase/view_bug.do?bug_id=8192884)
- javax.net.ssl.trustStore
- javax.net.ssl.trustStorePassword
- javax.net.ssl.trustStoreType
- javax.net.ssl.keyStore
- javax.net.ssl.keyStorePassword
- javax.net.ssl.keyStoreType
Certificate path validation
- CertPathValidator.PKIX
- jdk.certpath.disabledAlgorithms
- jdk.security.caDistrustPolicies
- com.sun.net.ssl.checkRevocation
- com.sun.security.enableCRLDP
- com.sun.security.crl.timeout
- sun.security.certpath.ldap.cache.lifetime
- com.sun.security.enableAIAcaIssuers
- ocsp.enable
- ocsp.responderURL
- ocsp.responderCertSubjectName
- ocsp.responderCertIssuerName
- ocsp.responderCertSerialNumber
Proxy
- http.nonProxyHosts
- https.protocols
- https.proxyHost
- https.proxyPort

Troubleshooting

To get more detailed logs, set the following properties:

java.security.debug
- https://docs.oracle.com/javase/8/docs/technotes/guides/security/jsse/JSSERefGuide.html#Debug
- https://docs.oracle.com/javase/8/docs/technotes/guides/security/jsse/ReadDebug.html
- suggested option: -Djavax.net.debug=ssl,trustmanager,handshake
javax.net.debug
- https://docs.oracle.com/javase/8/docs/technotes/guides/security/troubleshooting-security.html
- suggested option: -Djava.security.debug=properties,certpath

Servers

To see the protocols and ciphers supported by the server you are trying to connect to you can use tools such as Qualys SSL Labs if the server is publicly available or sslscan if you are in a private network.

Credits